Vacation Rentals By Owner In Chincoteague Island, VA

Showing 307 Of 307 Vacation Rentals

$242.39

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

Bath

Sleeps

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

Bath

Sleeps

Exceptional(34)

$386.69

/ Nightly

Condo

Historic Whealton House with full access to Waterside Inn facilites

Chincoteague Island, Virginia, United States

Charming condo with water view front deck and back deck with table and chairs. Fully equipped kitchen including microwave, stove, refrigerator, coffee maker, toaster, pots and pans, dishes/ serving items and utensils. Other amenities include central ac/heat, free WiFi, 2 T.V.'s, outdoor grill, and linens upon check in. Condo is located 1/2 mile from shops and restaurants in the Historic Main Street district. The condo is across the street from Waterside Inn hotel where the onsite manager and check in are located. You have full use of all hotel facilities during your stay in Sunset Hill Condo. Hotel amenities include seasonal outdoor heated pool, private fishing and crabbing pier, marina, boat trailer parking, fitness room & jacuzzi, and pickleball courts. Sunset Hill Condos are not wheelchair accessible, all units are non smoking, and we welcome short or long term rentals. We are located 3 miles from entrance to Chincoteague National Wildlife Refuge where the ponies run free. We offer spectacular views of the sunset, 4th of July fireworks, and rockets launched from Wallops Flight Facility. The condo is a short walk to the Chincoteague Carnival which takes place in July leading up to the world famous Chincoteague Pony Swim.

Bed

Bath

Sleeps

Exceptional(2)

$217.92

/ Nightly

Apartment

Stella della Baia | Brand New Chincoteague Getaway South of Downtown Near Carnival, Shops & Dining

Chincoteague Island, Virginia, United States

Welcome to 'Stella della Baia'! This is the perfect little getaway spot if you're looking for something simple, comfortable, clean and affordable. Everything is BRAND NEW and waiting for you! Located just south of downtown, Stella della Baia is conveniently located to the Fireman's Carnival, movie theater, downtown restaurants & shopping, and more. If you're traveling with a larger group but like the separate of your own place, check out 'Stella del Mare' ! Book both homes and receive a 5% discount off of each! brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- Pets are not 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.

Bed

Bath

Sleeps

$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

Bath

Sleeps

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

Bath

Sleeps

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

Bath

Sleeps

Rent a place that suits your needs

Condo

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Most popular vacation rentals in Chincoteague Island

Exceptional(13)

$700.50

/ Nightly

Private vacation home

House on the Dune by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$767.05

/ Nightly

Private vacation home

Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$859.07

/ Nightly

Private vacation home

Wildcat Haven | Luxury Bayfront Estate, Private 500' Pier, Dual Kitchens + Pet Friendly

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$1059.04

/ Nightly

Private vacation home

June's Retreat | Luxury Waterfront Estate w/ Panoramic Bay Views, Boat Dock, Billiards + Verandas

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$416.26

/ Nightly

Private vacation home

Off Belay | Luxury Creekside Home, Screened Porch, Fireplace & Gourmet Kitchen

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$404.32

/ Nightly

Private vacation home

Cockleshell Cottage | Accessible Oyster Bay II Home w/ Screened Porch, First-Floor Suite & Pets Ok

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$407.00

/ Nightly

Private vacation home

K and S Paradise by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$407.04

/ Nightly

Private vacation home

Canalfront home with Screened Porch by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$412.77

/ Nightly

Private vacation home

Sunset Bay Villa 206 | Luxury Condo w/ Waterside Balcony, Gourmet Kitchen + Pool & Fitness

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

Exceptional(13)

$442.82

/ Nightly

Private vacation home

Blue Sea Star | Quiet Oyster Bay Cul-de-Sac w/ Screened Porch, First-Floor Suite & Pet Friendly

Chincoteague Island, Virginia, United States

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Bath

Sleeps

Vacation Rentals By Owner In Chincoteague Island, VA

$242.39

$286.55

$386.69

$217.92

$500.52

$1132.59

$170.91

Rent a place that suits your needs

Most popular vacation rentals in Chincoteague Island

$700.50

$767.05

$859.07

$1059.04

$416.26

$404.32

$407.00

$407.04

$412.77

$442.82

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