Vacation Home Rentals By Owner In Chincoteague Island, VA

Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Island, the lighthouse, the wild ponies and the abundant wildlife. This spacious home boasts a complete line of amenities including a 600' pier/dock with deep water access, and waterside decks and screened porch. This home is great for boaters! The bright and airy open floor plan is highlighted with fine custom windows throughout that frame the beautiful, panoramic water views. In addition, there are 2 private master bedroom suites, both with private full baths, on the main living level. The second level features another two bedrooms and full bath plus a private sleeping area, so there is plenty of room for everyone! Wireless internet available. brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. 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.

Return | Waterfront Views, 600' Pier, Decks, Boat-Friendly, Lighthouse + Wildlife Vistas

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$687.93

DRAGONFLY POINT is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the home, you see the bay and canals from every window! The abundance of decking for entertaining will amaze you with easy access on both floors. Upper family room/loft with unobstructed views.The home has beachy-chic feel with built in bookcases, shiplap, custom fixtures and bathrooms, and more. Two master bedroom suites - upper and lower. Totally fenced in yard that has mature plantings, kayak launch with concrete pad, 120' pier that extends into the bay, comfortable screened porch and much more! Many updates recently including washer & dryer, brand new kitchen & appliances, new bathrooms, etc. SIMPLY BREATH TAKING VIEWS! Come for a stay at Dragonfly Point - it's one you surely will not forget! brbr- This property has a 7 night minimum stay year 'round. br- No smoking is permitted on the premises. br- Linens and towels are included with your reservation.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.

Dragonfly Point | Luxury Oyster Bay Waterfront w/ 120' Pier, Screened Porch & Panoramic Views

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$696.59

Fabulous, fabulous, fabulous! If you're looking for a large space to have a family vacation or reunion, this is it. This beautiful waterfront home is located on a tidal creek and boasts over 3,000 sq ft of living space. All amenities - central air, all kitchen appliances & washer/dryer, and so much more! The formal dining room is great for large gatherings. Beautiful back deck area with private pool for your enjoyment. Island Estate is a PET FRIENDLY home. Please Note: Pool is open Memorial Day weekend through end of season/last renter (weather permitting).brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival.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.

Island Estate | 5BR Waterfront w/ Private Pool, Large Family Retreat, Pet Friendly

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$1059.04

June's Retreat is Chincoteague Island's premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the expansive wrap-around verandas, you'll feel as though you're one with nature and your surroundings. Downstairs features a chef's quality kitchen, private billiards room, waterside glass atrium, living room, private den, formal dining room, sitting room and a bathroom. Upstairs you'll find 4 bedrooms with bathrooms (en suite), a sitting area and balcony. The panoramic views of Chincoteague Bay are unobstructed and unsurpassed. Come and see for yourself; we promise you won't be disappointed!brbr- Linens and towels are included with our reservation.br- No smoking is permitted on the premises. 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.

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

Chincoteague Island, Virginia, United States

4

Bed

5

Bath

10

Sleeps

$274.35

Give me the Sea, and a little Cottage just to be…..brbrWelcome to ‘Making Memories on Mumford’ - an adorable new addition to our Seaside Vacations’ Family! This cozy home is not just a place to lay your head each night - it’s like a visit with old friends - so warm, welcoming, and comfortable. Tucked in the heart of our Little Island by the Sea, you’ll feel a million miles from the real world, yet be close to everywhere you want to be. You’re only minutes from Assateague National Seashore, where our Wild Ponies roam free, as well as shops, dining, mini-golf, and Robert Reed Waterfront Park, home of free events all Summer, as well as a great spot to watch one of our incredible Chincoteague sunsets. brbrThe Living Area is just perfect for kicking back after a fun-filled day at the Beach, and enjoying comfy furnishings, Free WiFi, and Flat Screen Smart TV. It’s light and airy, with a tasteful coastal flair. Just perfect for a small family or 2 couples traveling together, there’s plenty of space for all, both inside and out. With that Chincoteague charm we love, plus the modern amenities you want and need, it’s a great vacation homebase that is also affordable!brbrJust off the Living Area, you’ll find the well-stocked Kitchen, with all the comforts of home. We just love the painted sea glass cabinets and beachy LVP flooring. A Stacked Washer and Dryer is also housed in the Kitchen for your convenience. Slip out the Kitchen door to find the coolest backyard oasis with a detached Screened Porch, and Patio with seating and Fire Pit. Dine al-fresco in the Screened Porch, and take in that salty, sweet sea breeze - there’s nothing like it. With both furniture for relaxing and a picnic table, it’s great for family dining, and perfect for a good old fashioned crab feast! On the patio, you’ll find lounge chairs for chillaxing around the Fire Pit, and sharing stories of the day’s adventures. Too hot outside Dine in the comfort of Central AC in the spacious Dining Room!brbrMaking Memories on Mumford sleeps 4 more than comfortably with 2 Bedrooms and a Full Bath. Bedroom 1 is dressed in calm, coastal colors promising a peaceful retreat, and has a comfy Queen Bed. Down the hall, Bedroom 2 has beachy blues and crisp whites, and both a Full Bed and Twin Bed. The Full Bath has a Tub/Shower Combo, and mosaic tile mural that we just love. brbrWhether you’re into soaking up sunshine or searching for ponies, Chincoteague Island truly has something for everyone! After a day of exploring, you’ll love being able to stroll down the street to the waterfront park and take in our spectacular sunsets, or enjoy an incredible dinner at Bill’s Prime - always one of our favorites. We hope that you will be Making Memories on Mumford this year with those who matter most, as well! brbrSeaside Vacations does not allow group rentals to guests under age 25. NO SMOKING! 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.

Making Memories on Mumford by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$309.71

Beach Blessing - May your blessings be countless, like grains of sand.....br br Welcome to Beach Blessing - a Brand New Chincoteague Island Vacation Home ready to make your Vacation Dreams come true! This breathtaking New Home is located on Boothe Street - a quiet and serene location nestled between Main Street and Willow, yet close to everywhere you want to be. You can easily walk or ride your bike to the Carnival Grounds, Restaurants, Shops, and Robert Reed Park, easily the best spot to catch our fabulous sunsets.br br This 3 Bedroom/ 2 Bath Custom Home simply oozes quintessential Island Charm. With peaceful Sea Grass Green Siding and a classic Silver Metal Roof, it looks as if it belongs in Coastal Style Magazine. A spectacular 4-Season Sunroom lines the front of Beach Blessing beautifully decorated with Beachy White Wicker, Shiplap Walls, and Coastal Beadboard Ceiling - what a wonderful place to curl up with a good book or sip your morning coffee. This gorgeous Cottage is designed with a Beachy Farmhouse Cottage Style - you'll love the relaxing colors of Sand & Sea, and gleaming Hardwood Pergo Floors that greet you as you enter Beach Blessing. br br On the first floor, you'll find a spacious Living Area comfortably furnished and ready to sink into after a day of fun in the sun. The Custom Stone Fireplace is simply stunning and will be so wonderful on chilly off-season evenings. You will love just sitting back and relaxing in this Family-Friendly, Open Floor Plan while enjoying the Free WiFi and Flat Screen Satellite TV. Just off of the Living Area is the Kitchen and Dining Area, both of which will thrill the Chef in your family. Preparing Family Meals, while still enjoying the company of family and friends is always a treat, and the flow of Beach Blessing makes this so easy. The well-stocked Kitchen will feature Gleaming Granite Countertops, Stainless Steel Appliances, and a dramatic Tile Backsplash. There is also an Island Breakfast Bar perfect for quick meals before heading out to explore our wonderful Island! You can even dine Al Fresco on the Screened Porch that lines the back of the Home, while taking in that salty, sweet breeze and listening to the whispering pine trees. Don't feel like cooking on Vacation Wander down to many fine dining options including The Ropewalk, Bill's Prime Steak & Seafood, Don's Seafood, and more. br br Beach Blessing also offers a 1st Floor Bedroom with comfy Queen Bed, Flat Screen TV, and a Full Bath with Tub/Shower Combo convenient to both Bedroom 1 and the Living Area. Upstairs, you will find 2 more spacious Bedrooms. Bedroom 2 is the Master and features another brand new Queen Bed, Flat Screen TV, and access to a gorgeous Full Bath with Double Sinks and a Tub/Shower Combo. Bedroom 3 is perfect for the kids to share with aTwin Bunk Bed and 2 Twin Beds, yet another Flat Screen TV, and lots of space. Sunshine and Natural Light pour in through many large windows illuminating this stunning Beach Home. br br Beach Blessing combines the very best of Indoor and Outdoor Chincoteague Living. With multiple Living Areas that take in the true beauty of our quaint Island, you can enjoy time with your family while still having plenty of room to stretch out and relax. Stay tuned and watch for new pics as this stunning Home progresses, but don't wait to Book, as time in this Beauty won't last long!br br Beach Blessing - Beach Days are the Best Days!br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.

Beach Blessing by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$340.97

Ocean East 1 - Because not all who wander are lost.......br br Welcome to Ocean East 1 on the Eastside of Chincoteague Island. This lovely End-Unit Townhome has it all - a comfortable layout, sweeping Views of the Assateague Channel & Lighthouse, Water Access, and even welcomes your well-trained Family Dog!br br As you enter Ocean East 1, all eyes will be on your breathtaking Views - you can already feel yourself beginning to relax. This End-Unit Townhome has all you need to make incredible Chincoteague Island Vacation Memories. You will love the Open Floor Plan that invites everyone to spend time together and share stories of the day's Adventures. On the 1st Floor, you will find a spacious Living Area comfortably furnished and a wall of windows to the water. Relax in the Central AC while enjoying the Flat Screen Cable TV and Free WiFi after a fun-filled day on the Beach. You won't want to leave the huge Bayfront Balcony just off the Living Area - just imagine sipping your morning coffee while watching the Herons & Egrets fish for their morning meal! The well-stocked Kitchen has all you need to make mealtime a bay breeze. Enjoy meals in the Eat-in Kitchen or Al Fresco on the Balcony. The 1st Floor also has a super convenient Half Bath just off the Living Area. There is also a 1st Floor Bedroom with a Queen Bed!br br Upstairs, you will find 2 more spacious Bedrooms and 2 Full Baths. Bedroom 2 is a Master with a huge King Bed, access to another Waterfront Balcony, and a Master Bath. You can see forever from here - what a great place to sink into an Adirondack with a good book. Bedroom 3 is ideal for the kids with 2 Twins and a Full Bed. There is even a Playstation 2 TV w/DVD Player when they need a little down time. There is also a 2nd Full Bath and Full Size Washer & Dryer upstairs!br br The Outdoor Living at Ocean East 1 is incredible, as well. Fish and Crab right from the dock, launch a kayak, or bring your boat! Being the End-Unit provides the home with more privacy, as well as a beautiful side-yard that Fido will love! Talk about keeping everyone happy!br br Comfortable. Affordable. Waterfront. Dog-Friendly. Ocean East 1 really does have it all. Give us a call to plan your time in Paradise today!br br Ocean East 1 - Where Dreams are made of sun & sand.....br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with $100 Pet Fee. Dogs MUST be current on Flea/Tick Preventative & Immunizations. No Cats. Please note that fireplace is for decorative purposes only and must not be used. Owner's have cats.

Ocean East 1 by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$631.16

Memories are timeless treasures of the heart….brbrWhen was the last time you took a Vacation that truly touched your heart and took your breath away They aren’t easy to find, but when you do, you never forget the special moments and the memories that were made. Belle Vue is THIS kind of Vacation - an Experience that you will never forget, not just a place to lay your head at night.brbrBelle Vue means “beautiful view”, and boy, did they name this home perfectly! Tucked directly on the water’s edge on the ever-popular East Side of Chincoteague Island, this majestic home overlooks the Assateague Channel and all the Creeks leading to it, as well as the Assateague Lighthouse - absolutely stunning Views in every direction! Watch Ponies graze from across the Channel, and Herons, Eagles, and Egrets fish for their morning meal, from pretty much every room in this house. And not that you needed more convincing, but all of this is less than 10 minutes to Assateague National Seashore, where our famous Wild Ponies roam free. brbrAs you pull into the driveway, that salty, sweet air will greet you with a hug, and you’ll know you’re “home”. It’s hard to unpack, because you can’t take your eyes off the Water - the Lighthouse - the Wildlife. The kids - and the kid in you - will have so much fun fishing and crabbing - right in your own backyard. And Belle Vue is perfect for Boaters, Kayakers, and water lovers of every kind - tie up the Boat in the back, and be on the water with a moment’s notice!brbrThis spectacular Custom Home is such a special place - it is a true “home”, and you can feel the Memories that were made there. With soaring Ceilings and warm Wood throughout, it exudes Coastal Charm. The open Living Area is perfect for relaxing after a fun-filled day at the Beach, and enjoying Flat Screen Smart TV. Comfortably furnished and decorated with Local Art and unique pieces gathered over the years, it’s so welcoming. Just off the Living Area, the Sunroom is the place to be - with huge Windows to capture the amazing Views, it’s a great place to curl up with a good book, or play a game with the kids at the table. Or, just “be” - just kick back and let the beauty sink in. brbrMealtime will be a bay breeze in the Well-Stocked Kitchen. Whip up some Fresh Local Seafood, which hopefully you caught, and dine in the comfort of Central AC at the huge Dining Table, which of course, also has breathtaking Views! Not one to cook on Vacation Many great dining options are a hop, skip, and jump away.brbrBelle Vue Sleeps 10 in 3 Bedrooms, plus a cool open Loft Bedroom the kids are sure to love. Bedroom 1 is the Primary Bedroom and located on the 1st Floor. With a comfy King Bed and Flat Screen Smart TV, this huge Bedroom is a restful retreat. The Attached Private Full Bath has both a Walk-in Shower and Tub. Next door, Bedroom 2 has a Queen Bed and serene Coastal Colors. A 2nd Full Bath in the hall has a Walk-in Shower and also houses the Washer and Dryer. brbrWandering upstairs on the other side of the Living Area, you’ll find the Open Loft Bedroom and Bedroom 4. The Loft Bedroom has 3 Twin Beds and is whimsically decorated. Just off the Loft is Bedroom 4, which has a Full Bed and a Queen Bed, and is decorated with a shabby chic flair. Another Private Attached Full Bath is in Bedroom 4, and also has a Walk-in Shower. brbrNow for the Outdoor Living at Belle Vue - just wow! This gorgeous home sits on the bank of the pristine Assateague Channel and Chincoteague Bay, which are absolutely teeming with life. Sit on the Deck in the morning, and you may see everything from Pelicans and Eagles, to Dolphins, Sea Turtles, and ponies grazing on the banks across the Channel. Hear the roar of the Ocean on a breezy day, and take in that amazing “marsh mud” smell, as we Locals call it - there’s nothing like it! The kids will feel like they’re in their own Discovery Cove, while those that Boat and Fish will be on the water reeling in the Flounder in no time flat. brbrSo, if you’re looking for an Experience - not just a house - don’t pass over Belle Vue - it’s sure to make your family’s Vacation Dreams come true!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. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.

Belle Vue by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

4

Bed

Bath

10

Sleeps

$361.27

Welcome to Oasis on Main — a charming retreat nestled in the heart of Chincoteague Island. This beautifully updated home sits right on Historic Main Street, offering the perfect blend of island convenience and peaceful seclusion. Step out front to explore the shops, galleries, and restaurants, just a short stroll away, or slip out back to your own private sanctuary - follow the winding brick path to cozy Seating Areas, where you can take in that salty, sweet sea breeze. The very definition of Oasis is a place or moment that offers peace, relief, or refreshment amid difficult or hectic surroundings. And in today’s world, we all need a little Oasis in our lives, don’t we What makes this wonderful home even more inviting It welcomes your family dog at no additional cost, because, after all - they’re family, too!brbrAs you step onto the Porch at Oasis on Main, you’ll find 2 cozy chairs beckoning you to sit a spell and sip some sweet tea - watch our Little Island by the Sea come to life in the morning, or the sunset at the day’s end. Open the door, and you’ll be welcomed by gorgeous Coastal Colors, gleaming Hardwood Floors, and cozy Furnishings. With a unique layout that is both cozy and spacious at the same time, the expansive Living Area is perfect for relaxing after searching for our Famous Wild Ponies at Assateague - which is only 5 minutes away! Kick back and enjoy Free WiFi, Flat Screen Smart TV, and different seating options. There’s also a convenient Half Bath on the 1st Floor that is also home to the Full Size Washer and Dryer.brbrMealtime will be a sea breeze in this well-equipped Kitchen with all the comforts of home. With tons of countertop space, and a Breakfast Bar for grabbing a quick bite before hitting the Beach, eating out each day won’t be necessary - unless you want to, that is! But you will not want to miss grabbing a morning coffee at Main Street Coffee Shop, right next door, or maybe some of Amarin’s famous Croissants, which is just around the corner, and both should be on your list!brbrDine in the comfort of Central AC in the spacious Dining Area, or slip through the French Doors in the Kitchen to probably the most serene octagonal Screened Porch we’ve ever seen, and dine amongst the shade trees and gardens. From here, follow the stunning brick path to the 1st Seating Area, where you’ll find a Charcoal Grill, Chiminea, and several chairs. This is the perfect place to unwind with your morning coffee or an evening glass of wine beneath the stars, while enjoying a fire.brbrAs you follow the winding path through so many different types of trees and plants, you’ll find another Seating Area, perfect for a little “me time”. Just past that is the real surprise - a Guest House with a Game Room! The kids - and the kid in you - will have a blast in this space, which is newly renovated, and has a Flat Screen Smart TV, Bar with Seating, Air Hockey Table, and a Sleeper Sofa! The overhead light does just illuminate - it plays music and changes colors - wow! Many family memories are sure to be made here!brbrBack at the Main House, as you wander upstairs, you’ll find 3 Bedrooms and a Full Bath with Tub/Shower Combo. Oasis on Main comfortably sleeps 10 with these 3 Bedrooms, the Game Room Sleeper, and in case you need more options, there are 2 Sleeper Chairs in the Living Area. Bedroom 1 is dressed in sunny yellows and has a comfy King Bed - plus, all Bedrooms have Flat Screen Smart TV. Bedroom 2, down the hall, has a Queen Bed, and right next door, Bedroom 3 has a Full Bed and a Twin Bed, and sleeps 3. You'll also take in beautiful Views of the Chincoteague Bay from the front Bedroom!brbrAll of this, and you’re only a hop, skip, and jump away from one of the most wild and pristine beaches in our country! Whether your passion is our Ponies, sunbathing, fishing, or shell combing, our beautiful beaches have so much to offer. But no glitter, no high rises, and no casinos - and we think that’s pretty awesome. brbrOasis on Main - The break from the hustle and bustle you’ve been dreaming about!brbrONE well trained dog welcome - must be current on vaccinations and flea/tick preventative, and must be pre-approved. Dogs must be leashed. Seaside Vacations does not allow group rentals to guests under age 25. NO SMOKING! 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.

Oasis on Main by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

1

Bath

10

Sleeps

$829.35

Welcome to the crown jewel of Chincoteague Island vacationing! This completely renovated five-bedroom, six-bathroom home offers a rental experience that transcends the ordinary, delivering the kind of coastal luxury that transforms a vacation into a lasting memory.brbrEvery detail of this stunning home has been thoughtfully reimagined from the ground up. Floor-to-ceiling windows flood the main rooms with natural light and frame what are arguably the best views on the island. Rise each morning to gorgeous sunrises painting the water in shades of gold and amber — a private spectacle that never grows old, though you might find yourself setting your alarm earlier just to catch every moment.brbrThe open great room serves as the heart of the home, seamlessly connecting the living, dining, and kitchen areas into one magnificent gathering space. Top-of-the-line appliances, including a wine fridge and ice maker, outfit the kitchen, making meal preparation a genuine pleasure rather than a chore. Whether you are hosting an elaborate dinner for the entire group or simply enjoying a quiet morning coffee, this space accommodates every occasion with effortless elegance.brbrEach of the five bedrooms features its own private bathroom, ensuring every guest enjoys personal comfort and privacy throughout their stay. Spacious and expansive decks extend the living areas outdoors, providing ample room for relaxation, alfresco dining, and soaking in the island atmosphere.brbrNestled within the popular Oyster Bay I neighborhood, this home places you in an enviable position to explore everything the island has to offer. Nearby attractions include the scenic Island Nature Trail for peaceful walks, the beloved Island Creamery for indulgent treats, and Maui Jack's Waterpark for family-friendly thrills. The pristine shores of Assateague Beach, home to the island's famous wild ponies, await just a short drive away.brbrThis exceptional vacation home represents Chincoteague Island living at its absolute finest. Book your stay and see what it's all about - there's no doubt you'll want to return time and time again!brbr- No smoking is permitted on the premises. br- Linens and towels are included with your reservation.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.

Salty Oyster | Waterfront living at it

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$645.77

Shell Shack - High Tides and Good Vibes….brbrWhen was the last time you took a Vacation that truly took your breath away ! If you have been looking for a true Vacation Experience - not just a place to lay your head at night - boy, do we have a wonderful surprise for you - welcome to Shell Shack!brbrThis incredible home is Brand New to our Seaside Family, and we couldn’t be more excited! Tucked directly on the Chincoteague Bay - right on the water’s edge - you can’t get more Waterfront than Shell Shack. Newly and beautifully renovated, it is the one you’ve been waiting for - AND, it has a Waterfront HOT TUB that you already cannot wait to experience! Fish, Crab, or launch your Kayak right in your own backyard - it is indeed a Water Lover’s Paradise!brbrAs you pull down the long driveway, you can smell that salty, sweet breeze, and hear the wind whisper through the trees - you’re on Island Time now! Climbing up just a few stairs to the door, you already cannot wait to see the Views. Stepping into the Entryway, you’ll be welcomed by Oyster Wallpaper that we couldn’t love more, and enveloped in Crisp White and Nautical Navy. Kick off your shoes and let the fun begin!brbrYou’ll love relaxing in the Living Area after a fun-filled day exploring Assateague National Seashore, which by the way, is less than 10 minutes away. Sink into the comfy oversized sofa and take in Bay Views from a wall of windows to the Water - there’s nothing like it! Decorated with a whimsical Coastal Flair, and unique Local Art, it’s an amazing place to just “be”. In the evening, gather the family for movie night on the Flat Screen Smart TV, or hang out on the Deck and listen to the Tree Frogs sing. brbrJust off the Living Area, you’ll find a wonderful Screened Porch with more amazing Bay Views, and that leads to a Waterfront Deck with comfy seating for all. Are you seeing a theme here yet !brbrThe Chef in your family will adore the Well-Stocked Kitchen with all the comforts of home. With beachy white cabinetry and lots of countertop space, mealtime will be anything but a chore! Dine in the comfort of Central AC with Views better than a 5 Star Restaurant! Grill Cheeseburgers in Paradise while watching Herons, Eagles, and Egrets fish for their dinner - it truly doesn’t get any better! After dinner, watch the sun sink into the Bay with a glass of bubbly in your Waterfront Hot Tub - just, wow. brbrShell Shack sleeps 8 in 3 beautiful Bedrooms, and with 2 Full Baths. Bedroom 1 and 2 are both on the 1st Floor, with a comfy King Bed and Queen Bed consecutively. A shared Full Bath with a Tub/Shower Combo is convenient to both. Wandering upstairs, you’re going to love Bedroom 3, which is so uniquely and cleverly designed! A huge room with 2 Queen Beds welcomes you, as well as a Loft that the kids - or the kid in you - will love curling up in with a good book. A 2nd Full Bath with a Walk-in Shower is also on this level. A Full Size Washer and Dryer are located on the 1st Floor for your convenience, as well. brbrThere you have it - the best of everything - a beautiful, well-appointed interior, and Outdoor Living that will blow you away! Just think of the amazing Memories you’ll make here at Shell Shack!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.

Waterfront Island home with Hot Tub by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

2

Bath

8

Sleeps

$360.56

Every Seashell has a story…..brbrAnd isn’t that what this life is about Our stories - our Memories - precious times spent with those who matter most. brbrWelcome to The Shell Hunter in the very heart of Chincoteague Island. This adorable Cottage is THE place to make memories, build dreams, and find treasures. Tucked on a super quiet side street, this beautifully renovated home simply oozes that quintessential Chincoteague Charm you love, yet has the Modern Amenities you want and need. And talk about an amazing location - you can walk to the Farmers Market, Island Creamery, Downtown Main Street Shops and Restaurants, and Robert Reed Waterfront Park, where Seaside sponsors many Free Concerts during the Summer season - and home of the most spectacular Chincoteague Sunsets. brbrAs you enter through the Covered Front Porch, you’re tempted to kick off your Flip Flops and sit a spell. Dressed in colors of sea glass and with a fun nautical flair, this may be a place you spend a lot of time. Sip your morning coffee here as you watch our sleepy Island come to life each day - and keep an eye out, because you may see one of our famous Saltwater Cowboys go by the house. brbrSlipping into this darling home, your jaw will drop when you see the gorgeous decor and thoughtful space the owners have created for you here. Refinished, yet rustic, Hardwood Flooring and muted Coastal Tones will welcome you into the Living Area, complete with comfy furnishings and Flat Screen Smart TV. Grab a book from the Bookshelf and cozy up and relax - you’re on Island Time now. brbrThe Chef in your family will love the Well-Stocked Kitchen, with all the comforts of home, and then some! With Stainless Appliances, beachy white Cabinetry, and tons of Natural Light, mealtime will be easy breezy. Whip up cheeseburgers in paradise, and dine in the comfort of AC, or Al-Fresco on either the Screened Porch or on the Deck in the Fenced Backyard - so many options! Speaking of the Screened Porch, just imagine relaxing on the Porch Swing and listening to the Tree Frogs sing - and ohhhh, the smell of that salty, sweet sea breeze - there’s nothing like it. brbrThe Shell Hunter sleeps 6 in pure comfort and style in 2 Bedrooms, and an upstairs Bonus Room. Bedrooms 1 and 2 are on the 1st Floor, with a Queen Bed and Full Bed consecutively. Both are dressed in gorgeous, serene Coastal Colors, and adorably furnished. Full Bath 1 is located in the Hall, and has a Tub/Shower Combo. Wandering upstairs, the Bonus Room is simply awesome and has a Sitting Area with a Desk, spacious sleeping area with a King Bed, and a 2nd Full Bath with a Walk-in Shower. The Bathroom also houses a Full Size Washer and Dryer for your convenience. brbrAll of this, and less than 10 minutes from one of the most pristine beaches in America, Assateague National Seashore, where our Wild Ponies roam free. Whether you indeed are a Shell Hunter, or enjoy fishing, sunbathing, swimming, or surfing, there’s surely something for everyone in your clan at Assateague! What won’t you find A busy Boardwalk, Arcades, and traffic - just our beautiful beaches as nature intended them to be enjoyed! So, clear your calendar, grab those who matter most, and let’s go Shell Hunting!brbrSeaside Vacations does not allow group rentals to guests under age 25. NO SMOKING! 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.

The Shell Hunter by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$817.24

Spend your precious vacation time at this truly stunning, one-of-a-kind architectural masterpiece! From the moment you walk in the French entry doors, you'll be wowed by the floor to ceiling windows and 3-sided glass fireplace. The chef's quality kitchen is brand new with stainless steel appliances and granite counter tops. There are multiple decks for enjoying some relaxing downtime and taking in the unobstructed views of Oyster Bay. Professionally decorated with clean, modern Bohemian-chic decor and furnishings, you'll find yourself surrounded by simple, upscale comfort. There's a 70 TV in the living room, and all the bedrooms feature their own flat-screen TVs and Amazon Echo devices. Stream all of your favorite shows from Hulu, Netflix or Disney+! Sunrise Shore is located in one of Chincoteague Island's most popular waterfront residential communities - Oyster Bay I. Conveniently located to Maddox Blvd. (Beach Road) and downtown Chincoteague, yet far enough to escape the hustle & bustle. | | The main level of this home features the main living areas (kitchen, dining room, living room), a powder room, a pool shower bathroom ,and the master bathroom en suite. The upstairs features 2 more bedrooms, both with private balconies, and a full bathroom. There's also an additional loft sleeping area. | | The outdoor areas offer exceptional entertaining and relaxation space. Cool off in the 10' x 40' saltwater in-ground pool, or gaze at the stars as you spend the evening in the 6-person hot tub. Dine al fresco on one of the many decks, all while enjoying the water views. There's plenty of room in the yard for a game of corn hole or catch. brbr- Linens and towels are included with your reservation. br- No smoking is permitted on the premises. 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.

Sunrise Shore | Waterfront Oyster Bay Home w/ Pool, Hot Tub, Panoramic Views & Modern Luxury

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$222.3

Sky above, Sand below, Peace within….brbrLife is short - and busy - OH, so busy. When was the last time you grabbed those who matter most and left it all behind, even if just for a few days ! If you’ve been longing for a Beach Break, we’ve got the perfect place for you, right here in the very heart of Chincoteague Island! brbrWelcome to The Virginia Lee - an adorable Vacation Home close to everywhere you want to be, yet will make you feel a million miles away from the real world. And what’s even better The Virginia Lee is part of our Flex-Stay with only a 3 night minimum - and welcomes your family dog at no additional cost (up to 2 dogs welcome - 50lb max each)!brbrThis adorable home is tucked on Wayne Road - less than 10 minutes from Assateague National Seashore, where our Famous Wild Ponies roam free. There is even a Trolley Stop at the end of the driveway - how convenient is that!brAssateague is one of the most visited National Parks in our Country, and after a visit there, you’ll understand why! Our Beaches are wild and wonderful - no boardwalk, no stores - just beautiful, natural Beach - it’s pure heaven. Whether you enjoy Fishing, Crabbing, and Clamming - or just sunbathing and searching for ponies - there’s sure to be something for everyone!brbrNow back to The Virginia Lee - y’all, this is not just a place to lay your head at night. This is not a hotel. The Virginia Lee is a HOME. There’s nothing like having room to spread out, a Full Kitchen, and a lovely Yard to relax and take in that salty, sweet sea breeze. brbrYou’ll love kicking back in the cozy Living Area with warm wood accents, Free WiFi, and Flat Screen Streaming TV, after a fun-filled day exploring our beautiful Little Island by the Sea. And just wait until you see the Views of the Assateague Lighthouse you have from the Living Area! Slip out to the Deck to catch some rays or just listen to the Tree Frogs sing. The Virginia Lee has a reverse floor plan with the Living Area upstairs to maximize Views, and a great layout for spending time together without ever feeling crowded. brbrThe Chef in your family will love the spacious Kitchen decorated in beachy blues and crisp whites, with all the comforts of home. Whipping up family meals will be a bay breeze - grill cheeseburgers in paradise on the Charcoal Grill, and dine at the large Dining Table in the comfort of Central AC, or Al-Fresco in the downstairs Picnic Area. Not one to cook on Vacation No worries, we’ve got you covered! You’re just a hop, skip, and jump away from many great dining options. brbrThe Virginia Lee sleeps 7 quite comfortably in 3 Bedrooms, plus a Sitting Room. Bedroom 1 is located just off the Living Area, and has a Full Bed. There’s a Full Bathroom with Tub/Shower Combo convenient to both this Bedroom and the Living Area. brbrWandering downstairs, there’s still lots to explore! Bedroom 2 has a comfy Queen Bed and access to the Deck on the back of the house. Bedroom 3 is perfect for the kiddos with a Twin Bunkbed, and this also leads to the back Deck. A small Sitting Room with a Twin Sofa Sleeper is great if you need additional sleeping space, plus makes for a wonderful nook to curl up with a good book. Down the Hall, you’ll find a Screened Porch - enjoy your morning coffee as you listen to the Gulls cry and our Island comes to life each morning. There’s also a Full Size Washer and Dryer for your convenience, should you need it. brbrIf you’ve been looking for the perfect Vacation Destination that won’t break the bank, The Virginia Lee is for you. Relax, rejuvenate, and reconnect right here in our little slice of heaven on Chincoteague Island!brbr2 Dogs welcome with no additional fee, but must be pre-approved in advance - 2 max - 50lbs max each. Must be current on Vaccinations, and taking Flea/Tick Preventative. No Smoking! Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Exterior Security Camera on property. 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.

The Virginia Lee by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$466.78

Welcome to Tranquility! This show stopper of a home is a brand new construction, featuring 2 bedrooms, 2 bonus rooms and 2.5 baths. Sleeps up to 11 with 1 king, 2 queens, 2 queen conversion sofa/sleepers and a twin fold-out sleep chair. Deep Hole Hideaway rental properties can accommodate up to 23 people by renting all 3 units in this complex! (based upon availability) Tranquility Great for family reunions or large gatherings! Please reach out to our office or check out Escape at Deep Hole and Serenity at Deep Hole for multi home bookings. brbrbrPet friendly, private and quiet. This property allows for entertainment and relaxation for both you and your kids! There is also outdoor seating, cornhole, a firepit, picnic tables and barbecues for additional recreation for your vacation. Book your stay today, this one won't last long! brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. 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.

Tranquility | New Build, Sleeps 11, Fire Pit, Cornhole + Pet Friendly

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$385.38

Check out Chincoteague's newest Piney Island vacation rental! Hailey's Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants! You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague. brbrHailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed. You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay! brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. 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.

Hailey's Roundhouse - New & Unique Home w/ Water Access!

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$301.37

Discover comfortable vacation living in this charming one-level ranch home. Crabby Pines offers a cozy retreat with three bedrooms and two bathrooms, providing ample room for relaxation and privacy. The house is ideally situated in a serene residential neighborhood and features modern amenities that ensure a seamless, convenient lifestyle.brbrEnjoy the convenience of being just minutes away from the public boat ramp at Fur Landing. Outdoor enthusiasts will appreciate the close proximity to nature trails and a dog park, perfect for morning jogs or leisurely evening walks with your furry friends. Oh, did we mention this home is pet friendly Additionally, the property is located near the 'Beach Road,' a vibrant area bustling with mini-golf, dining options, ice cream shops, and boutiques - offering endless entertainment options.brbrThis welcoming home is designed with practicality in mind, ensuring that each space is utilized efficiently while still exuding a sense of warmth and comfort. The property's easy access to local amenities, combined with its peaceful surroundings, makes it an ideal choice for anyone looking for a balance between nature and community activities.brbrWhether you're settling down with family or looking for a tranquil spot to return to after a day of adventures on the island, this home is sure to meet your needs. Embrace a laid-back lifestyle in Chincoteague with this delightful vacation home opportunity.brbr- No smoking is permitted on the premises. br- Linens and towels are included with your reservation.br- This home is pet friendly with an additional fee. Maximum of two dogs under 25 lbs. each; no cats. 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.

Crabby Pines | One-Level Chincoteague Ranch Near Boat Ramp & Beach Road Attractions, Pet Friendly

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$613.22

Ninety-five feet of private Chincoteague Bay shoreline. That's what's waiting in your backyard at Lookout on Main — along with a dock, a ladder, two kayaks, a canoe, crab pots, and front-row seats to the most spectacular sunsets on the island.brbrSet on South Main Street in one of Chincoteague's most coveted locations, this beautifully renovated 5-bedroom home is the kind of place families return to year after year. Floor-to-ceiling windows and soaring ceilings flood the living space with panoramic bay views, while the massive screened porch stretching across the back of the home was made for crab feasts, late-night conversations, and breezy summer evenings. After sunset, gather around the fire pit in Adirondack chairs and watch the stars come out over the water.brbrInside, the home was designed for relaxing together without ever feeling crowded. The main living area offers sweeping water views from nearly every seat, comfortable gathering spaces, and fast WiFi if you need to check in with the outside world. Just off the living room, the entertainment room features a 70-inch TV with Blu-ray player and sound bar — perfect for movie nights after long beach days.brbrThe open kitchen and dining area overlook the bay and are fully stocked for everything from pancake breakfasts to seafood dinners with the day’s catch. Prefer to leave the cooking to someone else Main Street’s restaurants, ice cream shops, and local favorites — including J&B Subs — are all just a short stroll away.brbrLookout on Main comfortably sleeps up to 10 guests across five bedrooms. Upstairs, the private primary suite features a king bed, waterfront balcony, and incredible bay views — the perfect spot for morning coffee or stargazing before bed.brbrDownstairs, a second family room gives everyone space to spread out. Bedroom 2 features a queen bed, Bedroom 3 has a twin bunk bed, Bedroom 4 offers two twin beds, and Bedroom 5 includes a twin-over-full pyramid bunk that kids are sure to claim first.brbrBut the real magic of Lookout on Main happens outside. Spend your days kayaking from the backyard, crabbing off the dock, playing yard games on the waterfront lawn, or simply watching herons and egrets drift along the shoreline. End the evening with a glass of wine as the sun melts into the bay and the sky turns shades of orange and pink you won’t quite believe are real.brbrThis is the kind of Chincoteague vacation people talk about all year long.brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. We do NOT rent to party groups, high school groups, or bachelor-type parties. 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 errors.

Waterfront home with spectacular sunsets by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$257.37

Life is good - but Island Life is better!brbrWelcome to The Salty Crab in the very heart of Chincoteague Island! This gorgeous Brand New Home is nestled on Church Street, just a short stroll from our famous Farmers Market and Downtown Historic Main Street’s many Shops and Restaurants. Robert Reed Waterfront Park is also only steps away and home of the most amazing Chincoteague Sunsets ever, as well as many Free Concerts and Events during the Summer season! If you like to be near the action, yet still feel a million miles away, The Salty Crab was made for you! Plus, you can bring the family dog along, making it truly a Vacation for the whole family!brbrYou’ll love relaxing in the Living Area with Colors of Sand and Sea, and a huge comfy Sectional Sofa with plenty of room for all. Enjoy Family Movie Night on the Flat Screen Smart TV, or kick back on one of the Covered Decks and share stories of the day’s adventures. The Salty Crab’s wonderful open layout is perfect for spending time together without ever feeling crowded. brbrJust off the Living Area, you’ll find the well-stocked Kitchen with Stainless Appliances and awesome Custom Butcher Block Countertops. You’ll love not having to eat out everyday - unless you want to, of course! Dine in the comfort of Central AC, or wander out to the Picnic Area - perfect for enjoying some Fresh Local Crabs! With a Gas Grill and cozy Fire Pit, The Salty Crab has all the makings of a wonderful Vacation you’ll never forget. brbrWandering upstairs, you’ll find 3 beautiful Bedrooms, which sleep 8 total. Bedroom 1 is a lovely Master Bedroom adorned in beachy blues and pinks, with a Queen Bed. Slip out to the Private Balcony to stargaze while everyone else slumbers, or just curl up in the comfy furniture with a good book. The Private Master Bath has a Custom Walk-in Shower. brbrDown the Hall, Bedroom 2 also has a comfy Full Bed. All Bedrooms are equipped with their own Flat Screen Smart TV, as well! The kiddos will love having their own space in Bedroom 3, which has 2 Sets of Bunk Beds and sleeps 4. A 2nd Full Bath in the Hall is shared and has a Tub/Shower Combo. brbrA fabulous Outdoor Area has been created in the Backyard, and will definitely be the place so many Vacation Memories are made. Tell tales that span many generations, or simply chase Lightning Bugs - just “be” together. Sounds simple enough, but we know this can be challenging in today’s world. brbrAside from the many Attractions you can actually walk to from The Salty Crab, you’re less than 10 minutes away from Assateague National Seashore, where our Wild Ponies run free. Whether you like searching for Ponies or shellcombing, there’s something for everyone. The Bayside’s shallow, calm waters are great for the younger swimmers, as well. And did you know that you can sit at the Oceanfront, and still watch the Sunset on the bayside Our little Island by the Sea is so special. Isn’t it time to see what magical gifts Chincoteague and Assateague can bring into your family’s life brbrNo Smoking. Dogs welcome - 2 max - with a $100 Pet Fee each. DOGS MUST BE APPROVED IN ADVANCE. Must be current on flea/tick preventative and vaccinations. 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.

The Salty Crab by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States