Home Vacation Home Rentals By Owner In Chincoteague Island, VA

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Exceptional(9)

$513.68

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Private Vacation Home

The Coastal Retreat by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Live for the moments you can’t put into words….. brbrWhen was the last time you took a Vacation that truly took your breath away A Vacation Home shouldn’t be just a place to lay your head at night - it’s the heart of your Vacation - a place to relax, rewind, and reconnect with those who matter most. A place to make memories, savor moments, and just “be”. Here at Seaside, we want you to have a Vacation Experience - and that is exactly what you will get here at Coastal Retreat on Tim Hill Lane. What makes it an even better Vacation You can bring your Family Dog with a $100 Pet Fee!brbrThis one-of-a-kind Home was designed as a replica of an 1800’s Coast Guard Station - and it has more character and charm than you could imagine. Perched on the banks of the Assateague Channel, you’ll experience Views that will take your breath away. With a Floating Dock for fishing, crabbing, and tying up your Boat, and a gorgeous, comfortable interior, Coastal Retreat has it all! You can even launch your Boat right down the street at Fir Landing Boat Ramp, and leave it right in your backyard!brbrCoastal Retreat is in a great mid-island location, just off Deep Hole Road, and a super short drive to Assateague National Seashore. Driving down Tim Hill Lane, you’ll feel as if you’re driving onto your own private island. A very private and quiet location, you can relax on the deck and take in that salty, sweet sea breeze while listening to the Tree Frogs sing. Seeing the Kayaks tucked under the house, you can’t help but feel giddy with excitement about the days ahead…..brbrYou’ll love kicking back in the Living Area with Flat Screen Streaming TV, comfy furnishings, and a wall of windows to the Water. Warm Wood Floors and a Knotty Pine Ceiling create such a welcoming room that you’ll never want to leave - except to slip out to the Channel Front Deck!brbrThe Chef in your family will love the Views from the Well-Stocked Kitchen with all the comforts of Home. Prepare meals with a Bay View, and dine in the comfort of Central AC, or out on the Waterfront Deck at the Picnic Table - perfect for enjoying some Fresh Local Crabs! Not one to cook on Vacation Gary Howard Seafood is right around the bend - pick up some Fresh Seafood already cooked, or some to cook later at the house yourself! Also just steps away is Captain Zack’s Seafood, and many other great Restaurants.brbrCoastal Retreat sleeps 8 more than comfortably in 3 bedrooms, plus the Loft. Bedroom 1 is on the 1st Floor and has a Queen Bed - perfect for those who don’t want to deal with more stairs. A Full Bath with a Tub/Shower is convenient to the Living Area and this Bedroom.brbrWandering upstairs, you’ll find 2 more Bedrooms and the Loft. Bedroom 2 is dressed in Sunny Yellows and Beachy Blues and has a Pyramid Bunk (Twin over Full) and sleeps 3. Bedroom 4 has a King Bed, Private Master Bath with Tub/Shower Combo, and fabulous Channel Views. The very cool Loft has not only a Queen Bed with Privacy Curtain, but also a Sitting Area with another Flat Screen TV!brbrThere’s no doubt that you will leave Coastal Retreat with precious memories that will last a lifetime. More pics of this fabulous Home will be coming soon, but don’t wait to make your Reservation, as it’s sure to fill quickly!brbrFriendly dogs are welcome with $100 Pet Fee per Dog - 2 Dog Max. Dogs MUST be current on Flea/Tick Preventative & Immunizations. No Cats.brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors. LINENS INCLUDED, NO SMOKING, NO VAPING. FAMILIES ONLY AND MUST BE AT LEAST 25.
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Bath 2

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Sleep 8

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Exceptional(2)

$264.23

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Private Vacation Home

Catch of the Day by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Memories at the Beach last a lifetime….. brbrHoping to land the big one this year for your Chincoteague Island Vacation Look no further than adorable “Catch of the Day” on super quiet and peaceful Tim Lane, just off Deep Hole Road, in the very heart of Chincoteague Island!brbrThis delightful Duplex sits tucked at the end of the Lane, surrounded by peaceful Shade Trees. Just imagine kicking back on the Front Porch and listening to the Tree Frogs sing. Kick off your Flip Flops at the door - you’re on Island Time now!brbrYou’ll love relaxing in the comfy Living Area and enjoying Free WiFi and Flat Screen Streaming TV. Warm colors pulled from Nature itself are warm and welcoming. With plenty of comfy seating, there’s room to spend time together without ever feeling crowded. Slip out the Sliders to the fabulous Screened Porch overlooking nothing but Nature - totally peaceful. What a wonderful place to begin and end every precious Vacation Day. There’s also a convenient Half Bath just off the Living Area.brbrThe Chef in your family will find meal prep a bay breeze in the Well-Stocked Kitchen! With all the comforts of home, whipping up the “Catch of the Day” is no problem, and you can enjoy it in the comfort of the AC, or Al-Fresco on the Screened Porch! No luck fishing Gary Howard Seafood is just around the bend, as is Captain Zack’s Seafood - yum!brbrCatch of the Day sleeps 6 more than comfortably in 3 Bedrooms. Bedroom 1 is on the 1st Floor with a comfy Full Bed. Wandering upstairs, you’ll find 2 more Bedrooms and a Full Bath. Bedroom 2 has a Queen, and rich reds and antique furnishings. Bedroom 3 is great for the kids with 2 Twin Beds, and brilliant blues and greens. The Full Bath has a Tub/Shower Combo, and has been newly renovated, as has the Half Bath downstairs.brbrSo, if you’ve been looking for the perfect place to relax, rejuvenate, and reconnect with those who matter most, cast a line and reel in this amazing Catch of the Day!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.
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Bath 1

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Sleep 6

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Exceptional(6)

$303.72

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Private Vacation Home

Channel View Charmer by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Channel View Charmer - Every moment has the potential to be amazing….brbr**Now Dog Friendly!** brbrLooking for the perfect beach getaway for your family Channel View Charmer will charm it’s way into your heart forever! This adorable Water View Home has to be in one of the best locations on our beautiful little island. Located adjacent to ever-popular Veteran’s Memorial Park, the world is your oyster (“arster” as pronounced here on our little island). Only steps away, you will find a fabulous playground, pier for fishing and crabbing, tennis and basketball courts, and a boat launch ideal for launching kayaks, as well as boats. brbrJust imagine enjoying your morning coffee on the Deck while watching Herons and Egrets dance over the Assateague Channel. Or stroll down to the dock to try your hand at fishing and crabbing. And you can enjoy a glass of pinot while watching the kids safely playing at the playground, just across the lane from the house.brbrAs you pull into the drive, you’re already thinking this will be anything but a boring vacation - there’s so much to do mere steps from the house! Channel View Charmer is adorned in colors from Mother Nature herself - muted Sea Grass Greens and Sandy beige - with fun pops of color throughout. We just love its retro flair - so warm and welcoming. brbrYou’ll love kicking back in the Living Area after a fun-filled day searching for seashells and wild ponies, and enjoying Free WiFi and Cable TV. Or perhaps lounge on the front Deck and take in that salty, sweet sea breeze as you watch the kids have a blast at the playground. Channel View Charmer’s open layout is perfect for spending time together, without ever feeling crowded. brbrThe Living Area opens to the Dining Area and Well-Stocked Kitchen - no need to eat out each vacation day, unless you want to, of course! Grill the Fresh Catch of the Day, which hopefully YOU caught, on the Charcoal Grill, and dine in the comfort of Central AC, or Al-Fresco on the Outdoor Picnic Table - also a great place to have a Crab Feast! Or, if the mood strikes you, wander down the street to Etta’s Channelside Restaurant, or super popular Mr. Baldy’s. Just off the Kitchen, you’ll find a convenient Half Bath, and Full Size Washer and Dryer. brbrChannel View Charmer sleeps 8 more than comfortably in 3 Bedrooms - 2 of which are upstairs. Bedroom 1, on the 1st Floor, has a comfy Queen Bed and a fun Nautical Theme. Wandering upstairs, you’ll find 2 more Bedrooms, each with 1 Full and 1 Twin Bed, with Bedroom 3 also having Flat Screen Streaming TV. A shared Full Bath with Tub/Shower Combo sits between the 2 Bedrooms. brbrIf you’re ready for a Vacation Experience, rather than just a place to lay your head at night, Channel View Charmer should be on your short list! Traveling with another family ! Book Channel View Charmer and Seaside Serendipity, right next door, together!brbr2 Dog Max with $100 Pet Fee each. Pets must be pre-approved. Pets must be current on vaccinations, and on Flea/Tick Preventative. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors. LINENS INCLUDED, NO SMOKING, NO VAPING. FAMILIES ONLY AND MUST BE AT LEAST 25.
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Bath 1

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Sleep 8

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Exceptional(9)

$238.04

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Private Vacation Home

Ava's Beach Cottage by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Ava’s Beach Cottage - Relax, Rejuvenate, and Reconnect…..brbrLife takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ava’s Beach Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern Amenities, there's no better home base for making Chincoteague Island Vacation Memories. What makes Ava’s even more special You can bring your family dog, so it’s truly a getaway for the whole family!brbrTucked in a great mid-Island location on Ridge Road, you’re close to everywhere you want to be - including Assateague National Seashore, where our famous Wild Ponies roam free! Whether you enjoy searching for Wild Ponies, Beach Combing, Fishing, or just Sunbathing, there’s truly something for everyone in your crew. Our Beaches are wild and wonderful - no highrises, no boardwalks - just beautiful Mother Nature! Did you know that Assateague National Seashore is the most visited National Park in our country Spend a little time here and you will discover why this is.....brbrAva’s Beach Cottage is just perfect for a Couples Getaway, or for a small Family. You’ll love curling up in the cozy Living Area after a fun-filled day at the Beach, and enjoying Free WiFi and Flat Screen Smart TV. Soothing Colors of Sand and Sea are warm and welcoming, and the sofa is also a Sleeper. If you’re one to enjoy kicking back in the great outdoors, you are going to love the Detached Screened Porch just steps away! Curl up with a good book on the Outdoor Sectional, or enjoy some Fresh Local Seafood at the Outdoor Dining Set - or maybe relax on the Porch Swing and share stories of the day’s adventures. Just take in that salty, sweet sea breeze, and just BE. Your pup is going to love having a Fenced Yard to run and play in - it’s just the perfect set-up for the whole family! There’s even an Outdoor Shower for rinsing off sandy feet.brbrMealtime will be a bay breeze in the well-stocked Kitchen. With everything you need to prepare everything from a quick bite before hitting the Beach, to Cheeseburgers in paradise for dinner, there’s no need to eat out everyday - unless you want to, that is! You have your choice of both a Gas Grill and a Charcoal Grill in the backyard, and there are also many great dining options nearby, if you do want a break from cooking.brbrAva’s Beach Cottage sleeps 6 in 2 Bedrooms, plus a Sleeper Sofa in the Living Area. Bedroom 1 is located on the 1st Floor, and has a comfy Queen Bed, gorgeous Coastal Colors, and a Flat Screen Smart TV. Just outside of Bedroom 1, you’ll find a Stackable Washer and Dryer, should you need it. The Full Bath is also on this floor, and has a Walk-in Shower.brbrUpstairs, you’ll find a very cool Loft-like Bedroom that sleeps 3. The kiddos will love this space, which has a Twin Bed and a Twin Bunk Bed. Please take note that there is not a Door on this Bedroom, which is at the top of the stairs, so this may not be a great option for very young children, and you can bring a gate along if you like, as well.brbrAva’s Beach Cottage is the whole package, y’all - adorable and affordable, this is the beach break you’ve been longing for. Give us a call to book your time on our Little Island by the Sea today!brbrWell-trained dogs allowed with non-refundable $100 Pet Fee each - 2 Max, and must be approved in advance. Pets must be on flea and tick preventative and current on vaccinations. No cats. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. LINENS INCLUDED, NO SMOKING, NO VAPING, FAMILIES ONLY AND MUST BE AT LEAST 25.
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Sleep 6

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Exceptional(13)

$279.17

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Private Vacation Home

Whispering Pines by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Trees listen to the Breeze; and then rustle its voice so beautifully….brbrLooking for a getaway that makes you feel a million miles from the real world Just imagine kicking back under the shade of tall Pine Trees - swaying in the breeze, while you listen to the Tree Frogs sing - pure bliss. Whispering Pines is not just a place to lay your head at night - it’s a feeling - a true Vacation Experience. Nestled on a quiet cul-de-sac in a great mid-Island location, you’ll be close to everywhere you want to be, including Assateague National Seashore, where our famous Wild Ponies roam free. And, Whispering Pines welcomes your well-trained dog with a $100 Pet Fee each - 2 max! Now, it’s truly a Vacation for the whole family!brbrAs you pull down the long lane to this beautiful Duplex, you’ll know you made the right choice. Even though it’s a Duplex, it offers so much privacy and space. You’ll enter through the fabulous Screened Porch that lines the front of the house - kick off your Flip Flops and let the fun begin!brbrYou’ll love kicking back in the spacious Living Area with Free WiFi and Flat Screen Smart TV. There’s even a cozy Seasonal Fireplace for those chilly Off-Season Stays. Whispering Pines is the perfect getaway for any season, and we absolutely adore our Little Island by the Sea in the quieter months, as well! Sink into the comfy furnishings after a day of fun in the sun, and just BE together - what a wonderful concept! We love the Open Layout of Whispering Pines - it’s perfect for spending time together without ever feeling crowded.brbrThe Living Area opens to the Kitchen and Dining Area. Well-Stocked with all the comforts of home, mealtime will be anything but a chore. With both a Keurig and Mr. Coffee type pot, everyone will enjoy their favorite morning brew. Dine in the comfort of Central AC, or wander out to the Screened Porch and dine Al-Fresco under the shade of the Pine Trees. Grab a quick bite at the Breakfast Bar before heading to the Beach to search for Wild Ponies, or pick up some Sandy Pony Donuts on the way! Speaking of Ponies, the backyard of Whispering Pines overlooks Historic Beebe Ranch, and you can often see Chincoteague Ponies right from your back Deck! Relax on the Deck or in the yard around the Fire Pit - so many cool places to just hang out at Whispering Pines.brbrWhispering Pines sleeps 9 in 3 Bedrooms and 2 Full Baths. Bedroom 1 is located on the 1st Floor and has a comfy Queen. Perfect for those who prefer not dealing with stairs, this spacious Bedroom has a Flat Screen Smart TV, and Private Access to the back Deck. Full Bath 1 is just across the hall, and has a large Vanity and Tub/Shower Combo. A Full Size Washer and Dryer is also provided for your convenience.brbrWandering upstairs, you’ll find 2 more Bedrooms and another Full Bath. Bedroom 2 is a huge room with soaring ceilings, sunny yellow walls, and a luxurious King Bed. The kids and grown-ups alike will approve of Bedroom 3, which sleeps 5! There is a Pyramid Bunk (Twin over Queen) and a Twin Bed with Twin Trundle. Both Bedrooms 2 and 3 each have a Flat Screen Smart TV, as well.brbrThe great mid-Island location of Whispering Pines means you’re pretty much 5 minutes from everywhere you want to be. A short drive to the Beach, Historic Main Street’s Shops and Restaurants, and more, you’re in the perfect location for all adventures Chincoteague! Your furbaby will love being able to tag along to many places, including Chincotiki, Island Creamery, and Leonard Waterfront Park, which is dog friendly, but unfortunately they can’t tag along to the Beach with you. But, they and you are going to love those peaceful walks amongst the Pine Trees at beautiful Whispering Pines! Plan your getaway today!brbrWell-trained dogs allowed with non-refundable $100 Pet Fee each - 2 Max, and must be approved in advance. Pets must be on flea and tick preventative and current on vaccinations. No cats. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements.
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Bath 2

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Exceptional(30)

$671.63

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Sunkissed Shores | Bayfront Retreat, Private Pier, Arcade Loft, King Suites & Epic Sunset Views

Chincoteague Island, Virginia, United States

Sunkissed Shores invites you to experience waterfront living at its finest. This expansive four‑bedroom, four‑and‑a‑half‑bathroom retreat sits directly on Chincoteague Bay, offering sweeping water views and unforgettable sunsets from every room. Each bedroom features its own private balcony and ensuite bath, including two king suites on separate levels for added privacy. A cheerful bunkroom provides flexible sleeping for families and groups, and thoughtful touches like two pack 'n plays and a highchair make traveling with little ones effortless.brbrThe heart of the home is the stunning great room, where soaring ceilings and dramatic walls of windows bring the bay right inside. During cooler months, the seasonal fireplace transforms this space into a warm, inviting haven—perfect for watching winter sunsets or enjoying a quiet evening indoors. A fully equipped kitchen—with generous counter space, quality cookware, and every gadget you could need—makes meal preparation and entertaining a pleasure. Just off the living area, an enclosed all‑weather gazebo opens to a large waterside deck, creating the perfect setting for crab feasts, morning coffee, or simply relaxing as the sky shifts from gold to pink each evening.brbrUpstairs, the game loft offers entertainment for all ages with a classic 1980s Space Invaders arcade machine, a commercial‑grade 4‑player arcade table with over 2,500 games, a 77 TV, board games, a chess/checkers table, and a giant wall‑mounted Connect 4. A queen sleeper sofa provides additional space for guests, and each upstairs bedroom sits in its own private wing for a peaceful retreat.brbr​​​​​​​Step outside to your private pier, where you can fish, crab, or launch kayaks directly into the bay. The bulkheaded shoreline offers easy access to the water, and the eastern side of the property provides serene sunrise views over the marsh—giving you the rare opportunity to enjoy both sunrise and sunset from the same home. With unmatched views, thoughtful amenities, and room for everyone to unwind, Sunkissed Shores stands apart as a place where memories are made and every day ends with a sunset worth savoring.brbr- No smoking is permitted on the premises. br- Linens and towels are included with your reservaiton.br- No pets are permitted on the premises.br- Any reservations made for a future year (known as Advanced Reservations) are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
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Bath 4

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Sleep 15

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Exceptional(8)

$354.58

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Private Vacation Home

Waterfront Wonder by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Sunsets are proof that no matter what happens, every day can end beautifully - and there is no better place to take in one of our famous Chincoteague Sunsets than fabulous Waterfront Wonder (formerly Sunset Foals). With gorgeous Newly Refinished, but still Historic, Hardwood Floors, and other upgrades, Waterfront Wonder still oozes the quintessential Chincoteague Charm you love, but also has the Amenities that you want and need.brbrLocated Waterfront on South Main Street, you'll be facing the most gorgeous Sunsets and Views of Chincoteague Bay. This beautiful Home is on an expansive lot with off-street parking behind the house, where there is also plenty of room to play and catch Lightning Bugs. Relax on the Deck while grilling the Fresh Catch of the Day and listen to the Tree Frogs sing. Wander to the front of Waterfront Wonder, and let the show begin - OH, those Views! The Waterfront Land across Main Street and directly on the Bay belongs to this special Home, so you will have your very own Private Pier to fish, crab, and clam - and you can even bring your small boat! Depth varies, but a shallow draft boat should be fine here, depending on the weather. There is a Kayak Launch off of the Pier to easily launch your kayaks to explore our wonderful waters. A couple of inviting Adirondacks and a Fire Pit wait for you by the water’s edge, and there’s a Picnic Table for meals right by the water. brbrAnd the house itself - just stunning. This lovely Home sleeps 8 more than comfortably in 3 Bedrooms. As you enter through the rear of Waterfront Wonder, there is a convenient Mud Room/Laundry Room for kicking off your Flip Flops. The Galley-Style Kitchen has all you need to make meal time a bay breeze. With Solid Surface Countertops and a lovely Tile Backsplash, it is both charming and well-equipped. Just off of the Kitchen is the huge Dining Room - just perfect for family meals and quick breakfasts before hitting the Beach. You can also dine Al Fresco on the Furnished Deck our back, or at the Picnic Area on the Waterfront side. AND, there's a delightful Breakfast Nook on the Waterfront Sun Porch, as well!brbrYou'll love relaxing in the spacious Living Room after a fun-filled day at the Beach. Sink into the comfy Sectional Sofa and enjoy Free WiFi and Flat Screen Smart TV, all while still taking in lovely Water Views. A great place to cuddle up with the family for Movie Night, or just curl up with a good book. And there’s a cozy Electric Fireplace for those chilly Off-Season Stays - one of our favorite times on our Little Island by the Sea. Lining the front of Waterfront Wonder is an awesome Front Porch/Sunroom that has Views that will change you - just breathtaking. What a wonderful place to enjoy your morning coffee and watch the Herons and Egrets fish for their morning meal. Just off of the Dining Area is Bedroom 1, which has a comfy Queen Bed and Attached Full Bath. brbrUpstairs, you will find 2 more spacious Bedrooms and another Full Bath. Bedrooms 2 has both a comfy Queen Bed and a Bunkbed with 2 Twins, and sleeps 4. Bedroom 3 has another Queen Bed, and all Bedrooms are decorated with a charming Coastal Flair. There is a large 2nd Full Bath upstairs with a Tub/Shower Combo. At the end of the hall, a welcoming little nook with a View beckons you to sit a spell and take in Bay Views that will knock your socks off. You will fall in love with the Vintage Wood Trim and touches of history throughout this special Home.brbrAnd of course, the water's edge is where you'll want to spend most of your time fishing, crabbing, and just taking in the spectacular Views. Waterfront Wonder is also very close to the Pony Parade Route during our famous Pony Swim! Stroll South just a few houses and watch this Historic Event! Don't wait to Book your time here - the calendar is sure to fill up fast!brbrWell-Trained dogs welcome with $100 Pet Fee each - 2 Max, and must be approved. Dogs must be current on vaccinations, and on Flea/Tick Preventative. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements.
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Bath 2

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Sleep 8

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Exceptional(4)

$403.53

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Private Vacation Home

Seahorse Shanty by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

At the Beach, life is different. Time doesn't move hour to hour, but with the flow of the Ocean. We live by the currents, plan by the tides, and follow the sun. When is the last time you can say you had a day like this Now is the time - grab the kids, the dogs, and the horses - that’s right - Seahorse Shanty is Dog Friendly!brbrSeahorse Shanty is a spectacular Brand New Custom Home just completed in 2023, and it was worth the wait. Sitting on 2 acres in a fabulous Mid-Island Location, you’ll be close to everywhere you want to be, yet still feel a million miles away from the real world. This statuesque home is nestled amongst whispering pines, and sits on 2 Horse Pastures. Don’t have horses No worries, because you’ll so appreciate the peace and serenity this expansive property offers - privacy, peace, and quiet. Pulling down the Lane to the house, you’ll know you made the right choice….brbrUpon entering Seahorse Shanty, you’ll be greeted by Colors of Sea Grass and Sandy Beaches - so lovely. The Open Layout is perfect for how we live today - spend time together without ever feeling crowded. Sink into the oversized Sectional after a day of exploring Assateague National Seashore, less than 10 minutes away, and enjoy Free WiFi and Flat Screen Streaming TV. There’s even a seasonal Fireplace for those chilly Off-Season Stays - one of our favorite times here on our Little Island by the Sea.brbrThe Chef in your family will love the Well-Stocked Kitchen, with all the comforts of home. With gleaming Granite Countertops, beachy White Cabinetry, and Stainless Appliances, mealtime will be a bay breeze. Between the Dining Table and Breakfast Bar, there’s plenty of room for the whole gang. Dine in the comfort of Central AC, on the Screened Porch (Furnishings on the way), or in the Shaded Picnic Area under the house - a great place to enjoy some Fresh Local Crabs and Chincoteague Oysters. Not one to cook on Vacation We’ve got you covered - you’re just a hop, skip, or jump away from many great dining options, and don’t forget to check out our awesome variety of Food Trucks - we’re known for them!brbrSeahorse Shanty sleeps 7 in pure comfort and style, all on the main level. Bedroom 1 is a Master with a comfy Queen Bed, Flat Screen Streaming TV, and a gorgeous Coastal Palette that’s sure to make it a restful retreat. The Private Master Bath has a stunning Custom Walk-in Shower and Double Vanity with Granite. The Rinnai On-Demand Water Heater ensures a hot shower for all. Slip out the Sliders to the Deck to listen to the Tree Frogs sing while the rest of your family slumbers…..brbrDown the Hall, Bedroom 2 has another Queen Bed, and Bedroom 3 sleeps 3 in a Pyramid Bunk (Twin over Full). All Bedrooms are equipped with a Flat Screen Streaming Only TV. There is a 2nd Full Bath with Tub/Shower Combo that is shared.brbrAll of this, and only a few miles from Assateague National Seashore, where our famous Wild Ponies roam free. Whether you enjoy fishing, shell-combing, or searching for ponies, Assateague has something for everyone, and is hands down one of the most stunning, natural beaches in America - no boardwalks, no shops, just Mother Nature at her finest.brbrOwner had exterior security camera. Up to 2 dogs max welcome at no additional fee.brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements.
Bed 3

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Bath 2

Bath

Sleep 7

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Exceptional(6)

$449.76

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Private Vacation Home

Whelks on Willow by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Whelks on Willow - Live in the Sunshine, Swim the Sea, drink the Wild Air..... brbrWelcome to Whelks on Willow - a lovely Coastal Cape Cod tucked away on Willow Street - close to everywhere you want to be, yet a million miles away from the worries of the real world. Featuring a refreshing Private Pool, Whelks on Willow is truly a Vacation Destination that sleeps 8 in comfort and style. brbrYou'll love relaxing in the Living Area with Free WiFi and Flat Screen TV after a fun-filled day at the Beach, which is only about 7 minutes away. With lots of oversized, comfortable furnishings, it truly has that home away from home feel. There's even a cozy Fireplace for those chilly Off-Season Stays - one of our favorite times on our little Island by the Sea!brbrThe Chef in your family will love the well-equipped Kitchen - mealtime will be anything but a chore! Well-stocked with all you need, there's no need to dine outbrevery day, unless you want to, that is! You can dine indoors in the comfort of the AC, or Al-Fresco on the huge Deck surrounding the Pool - talk about dinner with a view!brbrPool is seasonal, will be open from Memorial Day until Labor DaybrbrThe Sunroom that lines the back of Whelks on Willow is hands down one of our favorite places in this beautiful home. It's the perfect place to curl up with a good book, or for the kids to watch a movie. Stroll through the Sunroom and take a dip in the refreshing Private Pool - it's all yours! Catch some rays on the sun deck and take in that salty, sweet sea breeze. There's nothing like having your own tropical oasis - plus the beach is a short 5 minutes away!brbrAlso on the 1st Floor is Bedroom 1 with a comfy Queen Bed, Half Bath, and a spacious utility room with Full Size Washer and Dryer. Bedroom 1 is adorned in Coastal Blues and Whites - light and breezy, and has a Private Half Bath. brbrWandering upstairs, you'll find 2 more Bedrooms and another Full Bath. Bedroom 2 has a luxurious King Bed and tastel Coastal Decor. Right down the Hall, Bedroom 3 sleeps 4 with 2 Twin Beds, each with a Twin Trundle. A 2nd Full Bath is conveniently shared with a Shower. brbrWhelks on Willow - The perfect homebase for your next Chincoteague Island adventure!brbr*SUNDAY TURN DURING THE PEAK SEASON*brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
Bed 3

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Bath 2

Bath

Sleep 8

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$297.21

/ Nightly
Private Vacation Home

Saltwater Gospel by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Tucked in a very quiet part of our Little Island by the Sea, Saltwater Gospel is more than just a home—it’s a way of life. Time doesn’t move hour to hour, but mood to moment. We live by the currents, plan by the tides, and follow the sun….brbrYou don’t need a home that sleeps 8, but still want to enjoy the many benefits of staying in a true home, as opposed to a hotel No worries! This adorable Townhome in the heart of Chincoteague Island has all you need! Saltwater Gospel comfortably sleeps 8 in 1 Bedroom plus a Bonus Room and a Sleeper Sofa, and is only 5 short minutes to Assateague National Seashore - home of our famous Wild Ponies! brbrTucked away on Coach’s Lane, just off Maddox Boulevard (aka the Beach Road), Saltwater Gospel is the perfect getaway for small families, a small group of friends, or even a romantic retreat. You’ll enjoy walking or riding your bike to Shops, Dining, Amusements, and even the Beach! No need to break the bank for your next Chincoteague Vacation!brbrAfter a fun-filled day at the Beach, you’ll love relaxing in the spacious Living Area with oversized, comfy furnishings. With Free WiFi and Flat Screen Cable TV, it’s a great place to gather at the day’s end to share stories of the day’s adventures, or perhaps enjoy family movie night. We love the open layout of this adorable home - plenty of room for all to gather together without ever feeling crowded. brbrThe Chef in your family will appreciate the Well-Stocked Eat-in Kitchen with all you need to make mealtime a sea breeze. There’s plenty of room for all at the Dining Room Table, or you can dine Al-Fresco on the Deck in the private backyard with Dining Set. Not one to cook on Vacation We’ve got you covered - several great dining options are just a short stroll away!brbrAfter a day of memory making, you’ll appreciate sinking into the comfy Queen Bed in the Primary Bedroom. Dressed in beachy blues and whites, it’s sure to be a restful retreat. It also has an Attached Full Bath with Walk-in Shower. Down the hall, the Bonus Room is great for the kiddos or singles with 2 sets of Twin Bunkbeds. If you need another sleep option, the Living Room Sofa is also a Sleeper! A 2nd Full Bath in the hall has a Tub/Shower Combo. brbrThere’s so much to do on Chincoteague Island, that no one will ever be bored! Mini Golf and other Amusements are a quick walk for the kids - or the kid in you! And there’s nothing like being just down the street from one of the most pristine beaches in our country! So, if you could use a little Saltwater Gospel in your life about now, pack your bags and grab those who matter most - and we’ll see y’all at the Beach!brbrSeaside Vacations does not allow group rentals to guests under age 25. NO SMOKING AND NO PETS. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements.
Bed 2

Bed

Bath 2

Bath

Sleep 8

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Exceptional(5)

$336.91

/ Nightly
Private Vacation Home

The Mane Escape by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

We travel not to escape Life, but for Life not to escape us…..brbrWhen was the last time you slowed down - took time to watch the birds dance over the water, or just listen to the breeze rustle the trees Life is crazy - we know! We’re rushing to work, the kids are rushing to school - and the family pup just wants to tag along for all of it. What you need is an escape that the whole family can enjoy - and we’ve got it for you - all of you, including your furbaby! Welcome to The Mane Escape - brand new to our Vacation Rental Family - in the heart of Chincoteague Island. brbrThis beautiful home sits on North Main Street, close to everywhere you want to be. Combining all the quintessential Chincoteague Charm you love with the Modern Amenities you want and need, it’s sure to make everyone in your family super happy! Just a short drive or bike ride away is Assateague National Seashore - home of our famous Wild Ponies. Whether you like beach combing, sunbathing, or searching for ponies, your time on Assateague will be treasure forever. brbrYou’ll love relaxing in the gorgeous Living Area dressed in Colors of Sand and Sea. Sink into the oversized, comfy furniture and enjoy Flat Screen Cable TV with Streaming and Free WiFi. Just off the Living Area, and lining the front of The Mane Escape, is an awesome Screened Porch. Kick your feet up and take in lovely Views of deep water Lewis Creek, just across the street. Sunsets are pretty spectacular from the Porch, as well!brbrThe Chef in your family will absolutely love the Newly Remodeled Kitchen which is well-stocked with all you need. Nautical Navy Cabinets and Crisp White Countertops just scream Beach House, and the Backsplash is simply stunning. There’s even a Coffee Station with Coffee Grinder, Drip Coffee Pot, and Hot Water Dispenser. We highly recommend grabbing some fresh beans from Amarin Coffee - you’ll fall in love! Grill the Fresh Catch of the Day out back on the Gas Grill, and dine in the comfort of the AC in the huge Dining Room. There’s also a Full Bath with Walk-in Shower, and Full Size Washer and Dryer on this level. brbrJust off the Kitchen, lining the back of The Mane Escape, is a 2nd spectacular Screened Porch - and you’ll never want to leave this one. With a soaring Cedar Ceiling and comfy furnishings, you’re sure to begin and end every precious Vacation day right here. brbrThe Mane Escape sleeps 8 more than comfortably in 3 Bedrooms and 2 Full Baths. Wandering upstairs, Bedroom 1 has a comfy Queen Bed and overlooks Lewis Creek. Right across the Hall, Bedroom 2 sleeps 4 with a Twin Bed with Twin Trundle, and Full over Full Bunkbed - a perfect room for the kiddos. Bedroom 3, at the end of the Hall, has another Queen Bed and brilliant colors that just make you happy. The 2nd Full Bath is convenient to all Bedrooms and has a Tub/Shower Combo. brbrThe Mane Escape is all about experiencing Chincoteague Island - and there’s no better way to do this than living like a Local in a true Home - warm and welcoming. With the very best of both Indoor and Outdoor Living, it’s the perfect homebase for your next Island adventure! Relax, reconnect, and rejuvenate…..brbr*Well trained dog (2 max) welcome with $100 Pet Fee each. Must be current on Vaccinations and on Flea/Tick Preventative. NO CATS. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(10)

$242.39

/ Nightly
Private Vacation Home

The Pearl at Grand Bay by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Salty air breezes and the sweet serenity of pond-front living await you at The Pearl at Grand Bay. This Newly Remodeled End Unit Townhome has it all - magnificent Water Views, and a stunning interior. Located on the ever-popular East Side, you can have the Chincoteague Vacation you’ve been dreaming of at a very family-friendly price tag - and even your family dog can enjoy this Vacation!brbrIf you’re not familiar with the East Side, imagine driving down a quiet road that hugs the shoreline of the Chincoteague Channel - glancing out over the water, you will see only Assateague National Seashore and our famous Lighthouse - you may even see some ponies grazing in the marsh across the water! Grand Bay Court is in just the perfect location - you can easily stroll to Memorial Park to enjoy the Playground, Kayak and Boat Launch, Crabbing, Fishing, and more, and are just a short stroll from waterside dining at Etta’s Restaurant. brbrAs you pull up to The Pearl at Grand Bay, you’ll notice how lovingly landscaped and cared for this home is. Two Rockers on the charming Front Porch await you and a glass of Sweet Tea - kick off your flip flops and let the fun begin!brbrThe Pearl at Grand Bay has been completely updated - with floors reminiscent of a stroll on the Boardwalk and lovely Coastal Decor throughout, you will instantly feel relaxed. The Living Room with its comfy furnishings is a great place to chill after a fun-filled day on the Beach, and is well-equipped with Flat Screen TV for Streaming (No Cable) and Free WiFi. Wandering down the Hall, the spacious Eat-in Kitchen will wow you with Modern shades of distressed Grays and a stunning Custom Back Splash. Well-stocked with all you need, mealtime will be anything but a chore! There is also a convenient Half Bath and Laundry Area with a Full Size Washer and Dryer that will come in very handy.brbrAt this point, all eyes are on the doors leading to the amazing Outdoor Living at The Pearl. Wander out the Sliders to find a gorgeously manicured Pond Front Patio with jaw-dropping Views. Sit back in the Adirondacks and watch Herons, Egrets, and even Eagles fish for their morning meal. Dine Al-Fresco at the Outdoor Dining table and listen to the waves in the Channel, not far at all - breathe in that salty air we’re so famous for. Gather around the Chiminea in the evenings and share stories of the day’s adventures……brbrThe Pearl at Grand Bay sleeps 8 more than comfortably in 2 Bedrooms, plus two twins in the Living Area. Upstairs, the Master Bedroom is adorned in shades of Sea Grass and Sand Dunes and has a comfy Queen Bed. The highlight here is the Private Balcony overlooking the Pond and Views of the Assateague Channel - a great place to begin the day with your morning coffee! The Private Master Bath has a Walk-in Shower and lovely Vanity with lots of storage. Down the Hall, Bedroom 2 sleeps 4 with two twins and a queen. There is also a 2nd Full Bath upstairs with a Tub/Shower Combo.brbrMake some time to take some time with those who matter most - the Beach is calling!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Well-behaved dog allowed and at NO ADDITIONAL CHARGE. Dogs must be reported prior to arrival - 2 MAX. Must be current on all vaccinations and on flea/tick preventative.
Bed 2

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Bath 2

Bath

Sleep 8

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Exceptional(5)

$292.8

/ Nightly
Private Vacation Home

Pet Friendly Beach House by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

There is no time to be bored in a world as beautiful as this….brbrWelcome to The Robinson Family Beach House on our little slice of Heaven, Chincoteague Island. Located on ever-popular North Main, you'll enjoy the peace and quiet, yet still be close to everywhere you want to be. The Attractions of Historic Main Street with so many quaint Shops and Restaurants, Robert Reed Waterfront Park, and the Chincoteague Carnival Grounds are just a short drive away, as is the Beach and attractions on Maddox Boulevard - the Beach Road. With 3 inviting Bedrooms and 2.5 Baths, this charming Home is ready to make your family's Vacation Dreams come true!brbrAfter a fun-filled day exploring Assateague National Seashore and searching for our Famous Wild Ponies, you'll love coming back to the comfort of a true home, not a hotel room, with all the comforts of home. Rinse off in the Outdoor Shower, and relax in the comfortable Living Room and enjoy Flat Screen Streaming TV and Free WiFi. The Robinson Family Bach House feels a bit like you’re visiting an old friend - warm, comfortable, and relaxing. You’ll love the Historic Hardwood Floors throughout - so much character. Or sip Sweet Tea on the cozy Enclosed Porch, which lines the front of the house, and take in that salty, sweet sea breeze.brbrWander through the charming Curved Doorway, and you’ll find the Dining Area and Kitchen. The well-stocked Kitchen has all you need to make mealtime super easy. There’s also a Full Bath just off the Living Area - both Full Baths are located on the 1st Floor. There’s also a convenient Full Size Washer and Dryer in case you need to run a load of laundry.brbrThe Robinson Family Beach House sleeps 8 in 3 Bedrooms, without anyone ever feeling crowded. Just off the Living Area, Bedroom 1 has a comfy Queen Bed, Flat Screen Streaming TV, and is decorated with muted Coastal Colors - so relaxing. Wandering upstairs, you’ll find 2 more Bedrooms. Both Bedrooms 2 and 3 have a Full Bed and a Twin Bed, sleeping 3 in each room. Bedroom 2 is adorned with beachy blues and Flat Screen Streaming TV. In Bedroom 3, you’ll find a fun Fish Theme in crisp blues and whites, another Flat Screen TV, and a workstation for checking a few emails or finishing up a little Summer homework. These Bedrooms share a Jack and Jill Half Bath. brbrIf you’re looking for the quintessential Chincoteague Cottage, with old world charm you love, plus the Amenities you want and need, The Robinson Family Beach House is the place for you!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
Bed 3

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Bath 2

Bath

Sleep 9

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Exceptional(11)

$407.0

/ Nightly
Private Vacation Home

K and S Paradise by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Life’s a Beach - If you’re not barefoot, you’re overdressed….brbrWhen was the last time your Vacation made you happier than a Seagull with a french fry If you’ve been searching for just the right place - or just the right Experience, we should say - boy, do we have the place for you! K and S Paradise is nestled right in the heart of Chincoteague Island, and combines all the charm of yesteryear you love, with the modern amenities you want and need - and you can bring the family dog with a $100 Pet Fee, so no member of the family is left behind! Add in Water Access at the end of the street for crabbing and kayaking, and this is a deal that can’t be beat!brbrThis darling home sits on the East Side of Chincoteague Island at the end of the road, with no through traffic, so it’s nice and quiet. Fido will be chomping at the bit when he sees the great fenced-in yard, which makes for safer play time for both pups and the kids! With Views of the Assateague Channel from the 2nd Floor Deck that will take your breath away, you’ll find the perfect combo of location and amenities.brbrAs you enter through the Kitchen, you know the Chef in your family will be pleased with the ample Counter Space, Center Island, and all the gadgets you could need or want. No need to dine out everyday - unless you want to, that is! For family meals at home, you can dine in the comfort of Central AC in the huge Dining Room, or Al-Fresco on the Screened Porch, while taking in that salty, sweet sea breeze. brbrYou’ll love relaxing in the Living Area with Free WiFi and Streaming Only Flat Screen TV, and plenty of seating for all. Just off the Living Area is a small Sunroom - just perfect for curling up with a good book. brbrAlso on the 1st Floor, you’ll find Bedroom 1 with 2 Twin Beds and serene colors of sand and sea. A Full Bath with Walk-in Shower is convenient to both the Living Area and Bedroom 1. And just in case you need to do a load of laundry, there is a Full Size Washer and Dryer in the Laundry Room. brbrAs you wander upstairs, you will find Bedrooms 2 and 3. Bedroom 2 is easy, breezy - adorned in beautiful blues and greens, and has a comfy King Bed. Down the Hall, Bedroom 3 is light and airy with crisp whites, a Queen Bed, and gorgeous Views of the Assateague Channel. A 2nd Full Bath with Tub/Shower Combo is just down the Hall. brbrAnd speaking of Views, slip out onto the 2nd Floor Balcony to take in some of the prettiest Water Views. The Water Access is just across the driveway - the Kids will love trying their hand at crabbing and fishing. And on top of that, you’re just a few minutes from Assateague National Seashore, where our famous Wild Ponies roam free. brbrSo, if you’re looking for a Family Getaway that won’t break the bank, grab the kids - and the dog - and head on down to Chincoteague for the time of your life at K and S Paradise!brbrWell-trained dogs allowed with non-refundable $100 Pet Fee each - 2 Max, and must be approved in advance. Owners request that dogs not be allowed on couches/chairs to minimize wear. Pets must be on flea and tick preventative and current on vaccinations. No cats. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. LINENS INCLUDED, NO SMOKING, NO VAPING. FAMILIES ONLY AND MUST BE AT LEAST 25.
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(1)

$286.55

/ Nightly
Private Vacation Home

Bay Pony by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Isn't it time for a new romance.....with Life ! A visit to fabulous Bay Pony is certainly the place to begin. This phenomenal End-Unit Townhome is located in a wonderful little community, Silver Sails. One of the most unique and wonderful features of this Neighborhood is that it has a spectacular seasonal Community Swimming Pool for you to enjoy after a day on the Beach! This is a rarity on Chincoteague Island and your family will love having this amenity! Silver Sails is tucked in the middle of Chincoteague Island, with easy access to everywhere you want to be!brbrBay Pony.....where to begin This stunning 3 Bedroom/2.5 Bath Townhome has all the comforts of home, and is decorated with a tasteful Coastal Flair. Tucked away on a quiet, private cul-de-sac and backing to a gorgeous Tidal Creek, you will want to spend as much time outside as you will inside! Upon entering, you'll be swept away by the soothing colors of Sand and Sea. High ceilings, rich blues, and crisp whites make Bay Pony light, bright, and beachy. As you wander down the Hall to the Living Area, you will be welcomed by awe-inspiring Views of the Tidal Creek and nothing but beautiful Nature. brbrRelax in the Living Area after a fun-filled day of exploring Chincoteague, and enjoy the Free WiFi, Flat Screen Cable TV, comfy Furnishings, and even a Cozy Fireplace for chilly off-season nights. With a wonderful Open Floor Plan, the Living Area opens to the spacious Dining Area and truly a Chef's Kitchen. Mealtime will be a bay breeze in this incredibly well-equipped Kitchen with Gleaming Granite Countertops and awesome Water Views. There is plenty of seating in the Dining Area with seating for 6, and the Breakfast Bar is perfect for quick meals before hitting the Beach.brbrJust off the Living Area, you'll love hanging out on the wonderful Screened Porch with comfy furniture and amazing Water Views. Just imagine relaxing here with a glass of wine as the sun sets, ahhhh. Or kick back in one of the Adirondacks and take in that salty, sweet sea breeze. Grill the Fresh Catch of the Day, which hopefully you caught, on the Gas Grill, or maybe whip up some Cheeseburgers in Paradise. The kids will love catching Crabs and listening to the Tree Frogs sing as Mom and Dad take a breather. Make memories - isn’t that what it’s ALL about !brbrBay Pony sleeps 6 more than comfortably, featuring a 1st Floor Master Bedroom with Queen Bed, and a spacious Master Bath with Tub/Shower Combo. There is also a convenient Half Bath just off the Living Area. Upstairs, Bedroom 2 has another Queen, and Bedroom 3 has 2 Twin Beds - the perfect room for the kids. A 2nd Full Bath with Tub/Shower Combo is shared. brbrThis incredible Vacation Home truly has it ALL - and don't forget about the Community Pool, only a very short stroll from your front door! Enjoy all that our wonderful Island and Assateague National Seashore have to offer, and do it in style at Bay Pony!brbrBay Pony - Because the most important things in life aren't things.....brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
Bed 3

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Bath 2

Bath

Sleep 6

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$500.52

/ Nightly
Private Vacation Home

Nestled Inn by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Welcome to Nestled Inn - where time with family isn’t measured in minutes or hours, but in the memories that quietly become the best parts of our lives.brbrThis spectacular home was Brand New in 2025, and is absolutely stunning. Tucked on a super quiet Lane off the beaten path, you’ll feel a million miles away from the real world, yet still be close to everywhere you want to be, including Assateague National Seashore and Chincoteague Wildlife Refuge - where our famous Wild Ponies roam free. You're even just a short stroll from the Chincoteague Carnival Grounds. And if you’re looking to accommodate a large group or family reunion, Nestled Inn, Relax Inn, and The Feathered Nest are all tucked in this wonderfully quiet location!brbrYou’ll love relaxing in the Living Area after a fun-filled day at the beach. With muted colors pulled from nature itself and high-end luxury furnishings, you won’t be homesick here! Sink into the oversize sectional and enjoy family movie night together, or hang out on the Screened Porch and share stories of the day’s adventures. The open layout at this gorgeous home is perfect for spending time together without ever feeling crowded. brbrJust off the Living Area, the Kitchen will wow you. Mealtime will be easy breezy in this well-equipped Kitchen with all the comforts of home, and then some! We love the combo of beachy white cabinetry and flooring reminiscent of a stroll on a rustic boardwalk. Add in Stainless Appliances and gorgeous Shiplap Accents, and Nestled Inn is the perfect combo of style and function. Grab a quick bite at the Breakfast Bar before hitting the beach, or dine Al-Fresco on the awesome Screened Porch, which is furnished with furniture for both dining and relaxing. Not one to cook on vacation We’ve got you covered! You’re less than 5 minutes away from several great dining venues!brbrAfter dinner, check out the Patio with Fire Pit, roast some marshmallows, and make memories sure to be shared for generations to come. After all, isn’t this what life is about brbrNestled Inn sleeps 8 comfortably in 3 Bedrooms, and with 2 Full Baths, plus the Half Bath. Bedroom 1 is a desirable 1st Floor Primary Bedroom with a luxurious King Bed, Flat Screen Smart TV, and cool grays and whites, promising a restful retreat. The Attached Primary Bath has a Double Vanity and Custom Walk-in Shower. brbrWandering upstairs, you’ll find 2 more Bedrooms and a Full Bath in the hall. Bedroom 2 is enormous, and has a Queen Bed, Flat Screen Smart TV, and a Full Sleeper Sofa. Down the hall, Bedroom 3 also has a comfy Queen and Flat Screen TV. brbrAll of this, and keep in mind you’re only a short ride away from one of the most pristine beaches in America. Whether your pleasure is sunbathing, fishing, shell combing, or searching for Ponies, our pristine beaches offer something for everyone! Get Nestled Inn your next getaway - you won’t regret it!brbrNO SMOKING AND NO PETS. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(14)

$1132.59

/ Nightly
Private Vacation Home

Stoney Point by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Stop for a moment and imagine your dream vacation - what would it be like A spectacular Custom Home perched on the Assateague Channel with breathtaking Views Or maybe a Dream Home in which everyone has a Master Bedroom with Waterfront Balcony and Private Master Bath How about a warm and inviting Great Room where you can gather with those who matter most, while taking in Views one can only dream about There is such a place - and you will never want to leave Stoney Point!brbrStoney Point is located in ever popular Piney Island - which happens to be the closest community to Assateague National Seashore. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our country are just a short stroll or bike ride away. Did you know that Assateague National Seashore is the most visited National Park in our country Spend a little time here and you will discover why this is.....brbrLocated next door to Stoney Point is the community’s natural Kayak Launch, making your morning kayak tours even easier. Whether you enjoy spending time in the water, or simply relaxing with a glass of wine while enjoying the Views, Stoney Point is the place for you. brbrAs you drive down the winding road leading to Stoney Point, you’ll breathe deeply and take in the glorious smell of the Salt Air. You really can’t get much closer to the water than at this spectacular brand new home.brbrStoney Point is one of the most brilliantly planned homes and absolutely perfect for family gatherings. With parking for 4 cars, a spacious area under the house for storage, 2 Outdoor Showers, and plenty of yard for all of your toys, there is room for the whole gang here!brbrAs you enter the 1st Floor, you find Bedrooms 1 and 2, as well as the Laundry Room. Every Bedroom in this wonderful Home features a Private Balcony! Bedroom 1 features a spectacular Full Bathroom with Granite Vanity and Bath Tub/Shower, and a Queen Bed. Bedroom 2 also features a Queen Bed, and Full Bathroom with Granite Double Sink Vanity and lovely Custom Tile Shower. The Views from both of these bedrooms will simply take your breath away. Sweeping views across the Channel to Assateague - just imagine enjoying your morning coffee on your Private Balcony! Each Bedroom in this amazing home also has a Smart TV.brbrAs you climb a short set of stairs to the 2nd Floor, there will be no doubt in your mind you chose the right home to spend your vacation time relaxing in! With amazing Hickory Floors throughout, and soaring Pine Cathedral Ceilings, Stoney Point is the epitome of the “Open Concept Home”. The Chef in the family will love the Gourmet Kitchen featuring State of the Art Stainless appliances, Granite Countertops, a KitchenAid Range that overlooks the Assateague Channel, and a Wet Bar that has an Ice Maker! This kitchen has everything you will need, and then some!brbrThe huge Kitchen overlooks both the Dining Area and the Living Area, with plenty of seating for all. The Breakfast Bar seats 4, and the Dining Table can seat 8 comfortably. Just beyond this is the Living Area with Floor to Ceiling Windows framing the most spectacular water and Lighthouse Views ever! With Free Wifi, a 55 inch Flat Screen TV, High End furnishings and lovely Coastal Colors, you will never want to leave this room. Also on this level is a wrap-around deck, and an enormous Screened Porch overlooking the Channel featuring a picnic table to enjoy those Crabs al fresco, and also comfortable Wicker Furniture for relaxing and sharing the day’s stories.brbrWait - we aren’t done yet! Finally, you will climb another short set of stairs to the 3rd Floor, which features 2 additional Bedrooms. Bedroom 3 features a Queen Bed and another beautiful Full Bathroom, as well as a Private Balcony. Bedroom 4 features a King Bed, Master Bathroom with Granite and Custom Tile Shower, and more views that will WOW you!brbrThis amazing home is in a great location with easy access to the Beach, Fine Dining, and Entertainment. You may never want to leave the house, though!brbrStoney Point - Your Dream Vacation awaits you!brbrSeaside Vacations does not allow group rentals or rent to guests under age 25 - Families only - No HS Senior Groups, Bachelor-Type Parties, etc. Therefore, online bookings for group rentals will not be honored.brbrEvery effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any error.
Bed 4

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Bath 4

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Sleep 8

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Exceptional(13)

$170.91

/ Nightly
Private Vacation Home

Serendipity on Chincoteague - The perfect getaway!

Chincoteague Island, Virginia, United States

Just give me the Sea, and a little Cottage just to be…..brbrWork, meetings, school, traffic, homework, repeat - right ! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most - giggle, frolic on the Beach, and make memories that will forever be treasured. Take in that salty, sweet sea breeze - you’re on Island Time now. And if you can make the time, you won’t be disappointed. Welcome to Serendipity in the very heart of Chincoteague Island…..brbrThis adorable Newly Renovated Duplex is tucked on Willow Street - peaceful and quiet, yet close to everywhere you want to be. You can walk or ride your bikes pretty much everywhere on the Island from this location, but you will be just as happy kicking back on the Screened Porch and listening to the Tree Frogs sing. brbrAs soon as you walk through the front door, you’ll fall madly in love with Serendipity’s whimsical Coastal Style - there’s something to admire everywhere you look! So much love and care has been put into making it the perfect home base for your visit to our beautiful Little Island by the Sea. Enjoy kicking back in the Living Area with Free WiFi and Flat Screen Streaming TV after a fun-filled day at the Beach. There are plenty of books, and the Screened Porch is the perfect place to curl up with one and enjoy the sunshine. Just having been Newly Renovated, Serendipity is like brand new inside, and can’t wait to help you make amazing Memories!brbrJust off the Living Area, the Chef in your family will adore the Well-Stocked Kitchen, with all the comforts of home. With every gadget you could need, mealtime is sure to be a bay breeze. Dine indoors in the comfort of the Central AC, or steam some Fresh Local Crabs and dine Al-Fresco on the Screened Porch. Need a break from cooking while on Vacation There are so many great dining options within just a few minutes - dine waterfront at The Ropewalk and take in amazing sunsets, or treat yourself to Bill’s Prime Steak and Seafood - one of our favorites! Also tucked away in the Kitchen is a Brand New Stainless Washer and Dryer. brbrSerendipity sleeps 6 more than comfortably in 2 Bedrooms, plus a Sleeper Sofa in the Living Area. The Master Bedroom is dressed in beachy blues and sunny yellows, and features a Queen Bed and Flat Screen Streaming TV. The Private Master Bath has a Tub/Shower Combo. Just around the corner, Bedroom 2 is fun and eclectic, with 2 Twin Beds and another Flat Screen Streaming TV. There’s a 2nd Full Bath with Tub/Shower Combo in the Hall, also convenient to the Living Area. brbrSo, if you’ve been looking for the perfect Chincoteague Vacation - without breaking the bank - Serendipity is the place for you! Need a little flexibility in your life Serendipity is part of our awesome Flex-Stay Program, and only has a 3 night minimum ALL year long! Arrive any day you want - leave any day you want!! The world is your Oyster here with Seaside Vacations!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
Bed 2

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Bath 2

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Sleep 6

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