358,603 properties available

Located in Chincoteague, Virginia, United States. Cattail Cottage-quite and cozy cottage with a view Beautiful home in a pristine, natural setting.Enjoy wildlife and sunrises.Great wraparound porch. Crabbing/kayaking dock.First floor features:Den/Bedroom offers a private sitting area and twin/2 twin trundle bed.Full hallway bath, kitchen, and comfortable living room.Second-floor features:Queen bedroom with waterfront sitting area.Morning coffee overlooking sunrises and nature...It doesn't get better than this!Shared hallway full bath.A second bedroom with two twins.Cattail Cottage is completely equipped for Vacation Fun:Rec. Room with Ping Pong Table & Games,Kayaks, Bikes, and Crabbing Dock

Located in Chincoteague, Virginia, United States. Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location! We WHELK-come you and your family to come stay at our unique island vacation home. The idyllic island of Chincoteague offers an array of vacation experiences, and we are located in the heart of it all! Use our kayaks, bikes, and boogie boards by day, and take advantage of our convenient proximity to downtown by night. Our family fell in love with this slice of paradise many years ago, and we want to give you and your family the opportunity to experience all its beauty with the best stay possible.~ABOUT THE HOUSE~This is a 3 bedroom, 2 bathroom, 1221 sq. ft. beach house located in town. We have a full kitchen, living room, dining area, office space, and screened-in porch. This house is perfect for a large family or two small families. We comfortably sleep 8 but can sleep a maximum of 10 with use of our sofa bed. Our second floor includes an additional small living space with a Smart TV and an attached bathro

Located in Chincoteague Island, Virginia, United States. Captain's Rest - Lovely Waterfront on Marsh Island! Captain's Rest is now Flex-Stay ALL year long!We travel not to escape Life, but so that Life doesn't escape us. It's so hard to find time to break away from the daily grind and spend time with those who matter most - but, we all know there's nothing more important. Make time to make Memories, because we've got the place for you! Welcome to Captain's Rest - a Brand New Luxury Townhome located on Marsh Island, directly across the Channel from Chincoteague Island. As you take the exit for Marsh Island from the Causeway, you'll feel like you're pulling onto your own private island. With only a handful of homes here, you'll love the peace and quiet that Marsh Island offers. All the festivities of Chincoteague Island are mere steps away, but you return to the sweet serenity that only Marsh Island offers. This tiny Island was formerly a Harbor for Commercial Fishermen that was converted to Waterfront Homes. At Captain's Rest, take in Bay Vi

Located in Chincoteague, Virginia, United States. Waterfront 5 star: NEW... Discounted weekly rate for August 3-17 2024! Baywatch House is a waterfront home ideally suited for a Chincoteague Island vacation. Facing South looking over the water is the living room, dining room, kitchen, master bedroom and one of the other two bedrooms, a 50'+ deck with grill, lounge chairs, and dining area. The outside dining area is within view of the wonderful sunsets to the west and waterfront to the south.. Weber grill with all the tools provided. There is a large bonus room with dining areas facing North and West so beautiful views of sunsets are possibleMain living space: There are 3 bedrooms: Master bedroom has a comfortable king bed with 2 closets and private bathroom with a walk in shower & 6' soaking tub. Waterfront Bedroom #2 has a comfortable queen bed and direct access to a Jack and Jill bathroom with a tub/shower combo. Salt Marsh Estuary View Bedroom #3 has a queen bed & twin daybed with direct access to Jack and Jill bathroom

Located in Greenbackville, Virginia, United States. Kick back and relax at “Knot Stressed” in total comfort. This single floor 2 Bedroom, 2 Bath offers all the comforts of a home away from home that will not disappoint. Self check-in, free wi-fi, spacious back yard with BBQ and fire pit (wood provided while it lasts) and picnic table.Our Community offers golf (for a fee), playground, pickleball (for a fee), and basketball courts, Pro Shop with snack bar (open daily), one indoor and 2 outdoor pools, Tikibar (weekends only), restaurant (opens at 4pm with Happy Hour and specials from 4-6pm) and boat ramp and all are within walking distance or a very short drive. More information is contained in the House Manual.Pool passes available upon request, are non-refundable, $15/day or $75/week Per Person plus a $50 Community fee, ages 4 and under FREE and must be purchased in advance by Owner. Request passes through your booking.Please inquire about the boat ramp if you plan to bring a boat, there is a fee. There is room to park your boat on

Located in Chincoteague Island, Virginia, United States. Sunset Bay 306 - Spectacular Bay Views and a Bayfront Pool! Island Days and Sunny Rays…..Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous Condos sit directly on the Bay with stunning Views of the Bay, Marsh, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop and dine in the Historic District. ‘Our Pleasure’- Sunset Bay 306 - offers the Luxury you want, the Amenities you need, and Bay Views that will leave you breathless, all at a family-friendly price! AND, you’re welcome to bring the family dog with NO Pet Fee (1 Dog under 35 lbs only). Traveling with a larger group? You can rent Sunset Bay 306 and 307 - right next door!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, where our

Located in Greenbackville, Virginia, United States. Casa Playa - Only 25 min. to Chincoteague! Casa Playa - Peace, Love, and Sandy Feet……Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Casa Playa is all about - kicking back, taking in that salty, sweet sea breeze, and enjoying life again. Leave your worries behind - kick off your Flip Flops and let the fun begin!Casa Playa is located in fabulous Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. Captain’s Cove is only 25 short minutes by car or boat from Chincoteague Island and Assateague National Seashore, where our famous Wild Ponies roam free. And have y’all heard about our Oysters (pronounced Arsters here on the shore)? They are second to none! Looking for some OC excitement? Ocean City, Maryland is a short 45 minute driv

Located in Chincoteague, Virginia, United States. COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL 2024 Looking for the quintessential Chincoteague island experience to make lifelong memories? Welcome to COTTAGE BLUEFISH , a Chincoteague Island hideaway retreat lovingly restored and newly available for the 2024 rental season. This island cottage offers classic Chincoteague seaside look & vibe, combined with fresh, clean, newly remodeled everything. Discerning guests will not be disappointed.Every room has been thoughtfully updated, furnished with fresh fixtures, cozy furniture, and charming coastal decor. The kitchen is equipped with the full compliment of high-quality stainless steel appliances and all new cookware & glassware — everything you need to prepare a gourmet meal or entertain friends. The breakfast bar will quickly become a favorite coffee spot to gather and plan the day ahead. Later, sink into the comfy couches and relax following your adventures. After a day at the beach you’re sure to apprec

Located in Chincoteague, Virginia, United States. Sweet cottage with outdoor shower Our cozy cottage had been completely renovated with washer, dryer, all new stainless steel appliances, new wood floors, open concept, outdoor shower with hot water, new AC and heat. All smart TVS in bedrooms and living area. Front deck to enjoy morning breakfast. Located in perfect location to ride bikes or walk anywhere on the island. 5 minute car ride to beach. Toys, beach chairs and beach chairs available to enjoy the beach.

Located in Chincoteague Island, Virginia, United States. The Brass Crab - Check in/out any day! This charming rancher is ready to welcome you and your family. Come make memories in the cozy and relaxing space. Enjoy this redone home on large lot perfect for family games of kickball and tag after a fun day at the beach. This home sleeps 8-9 folks comfortably. It has a stocked kitchen, a dining area and living room with 4 bedrooms and 2 full bathrooms. There is an outdoor shower and foot rinse (April-November). Just added for Fall 2024: Disc Golf unit for the backyard and 8 new outdoor chairs. The driveway can hold roughly 8 vehicles, please do not park (or drive) on the grass. This home is walking distance to the Veterans Park (.8 mile) and is away from the town's bustle. We are a 7 minute drive to the beach and roughly a 20 minute bike to the beach. The Brass Crab is set up with families in mind with child friendly spaces, bunk beds and open places to play, but can easily work for 3 coup

Located in Temperanceville, Virginia, United States. LABOR DAY WEEKEND SPECIAL!!! QUIET retreat with HOT TUB & without getting BIT! Enjoy all the Eastern shore of Virginia has to offer! Welcome to Messongo Lodge! Listen to the owls & woodpeckers while having a drink by a fire in the screenhouse. Screenhouse is also equipped with gas grill, charcoal grill, & 2 regular size gas burners. Screenhouse= NO BUGS! Watch the deer, turkey and other wildlife in the 20 acre field from the screen house or hot tub of the screened in lodge porch.....(don't forget your binoculars) or enjoy the game on tv from the hot tub if you prefer. Screen-porch = NO BUGS! And your very well behaved 4-legged (and 2 legged) children will love running and playing ball in the spacious yard. In the spring/summer, enjoy the purple martins, hummingbirds, eagles, hawks, butterflies, dragonflies, bats and other winged friends! And if you're really lucky and happen to be staying during a Wallops Island launch...you can view it from the backyard. There are also several boat

Located in Chincoteague Island, Virginia, United States. Seabiscuit Surfside on Chincoteague Island! There’s no place like home ~ except for the Beach, that is!Welcome to Seabiscuit Surfside on Chincoteague Island, or as we like to call it, “Our Little Island by the Sea”! Seabiscuit Surfside offers you both - a beautiful home away from home, AND it’s less than 10 minutes from Assateague National Seashore, where our famous Wild Ponies roam free! Assateague National Seashore is the most visited National Park in our Country - after just one visit, you’ll understand why. Our Beaches are nothing but nature - no boardwalks, no high rises, no arcades - just beautiful, natural Beaches!This cheerful yellow home sits in the heart of our Island on Poplar Street - a quiet location, yet close to everywhere you want to be. Historic Downtown Main Street Shops, Dining, and our Waterfront Park - home of many free concerts during the Summer months, are all just a short stroll away. Seabiscuit Surfside is the perfect blend of the Chincoteague Charm you love, p

Located in Chincoteague, Virginia, United States. On a Whim, a family retreat! Relax with the whole family at this peaceful place to stay. Our house is located close to restaurants, beach entrance, and family friendly activities. You will love our house, located on a quiet private street but just a short walk to explore Chincoteague.

Located in Chincoteague, Virginia, United States. Family Oasis Handicap accessible and Dog friendly This home is very close to Historic Main Street, close to shops, restaurants, and local attractions, just minutes away from Maddox Blvd. You will be in the middle of the best of the island. This house is perfect for a large family or group of friends. It provides plenty of parking for your cars, boats, or any other vacation necessities! It is handicap accessible with a ramp leading to the back entrance. There is also a large fenced in area that your pup will have plenty of room to run around!Welcome to Family Oasis! This 4 bedroom, 3 bathroom house is pet friendly and newly renovated! When you book this rental you may fall in love with the cozy, beachy aesthetic before you realize its prime location! But when you do, you'll notice it is centrally located on Ocean Blva. This home is very close to Historic Main Street, close to shops, restaurants, and local attractions but also just minutes away from Maddox Blvd. You will be in the middl

Located in Chincoteague Island, Virginia, United States. Your next Vacation is Shore to Please! Beach More, Worry Less…..If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New Addition to our Seaside Family has it all - that quintessential Chincoteague Charm you love, the Modern Amenities you want and need, and a fabulous Mid-Island Location - close to everywhere you want to be!Shore to Please is tucked on Chicken City Road, in the very heart of our Little Island by the Sea. You’re less than 10 minutes - if that - from Assateague National Seashore, as well as a short stroll to Downtown Main Street’s Shops and Restaurants. Sleeping 10 in 4 Bedrooms, it’s the perfect home for 1 large family, or for 2 small families to share! Both affordable and adorable, it is the best of both worlds. What makes this even more special? You can bring your faithful family furbaby - up to 2 well trained dogs allowed with a $100 non-refundable pet fee. You’ll love relaxing in the Living Area after a fun-filled day at the Beach

Located in Chincoteague Island, Virginia, United States. Lighthouse Overlook - Amazing Views! Lighthouse Overlook - Every day should be a Beach Day…..Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Lighthouse Overlook was made for - kicking back, taking in that salty, sweet sea breeze, and enjoying life again. Leave your worries behind - kick off your Flip Flops and let the fun begin!Lighthouse Overlook is tucked away on the ever-popular East Side of Chincoteague Island. Overlooking the Assateague Channel, and of course Assateague Light, you’ll be welcomed by beautiful Water Views that will draw you in - the sweet, salty sea breeze drifting over the water to greet you - ahhh, you may never want to leave. This cozy home is just perfect for a small family, or 2 couples traveling together. Sleeping 4 in 2 spacious Bedrooms, yet wit

Located in New Church, Virginia, United States. Secluded Home near Chincoteague Island with VB&BB ***Private Sand Volleyball and Basketball courts were added this year***Green Woods is a newly renovated 4 bedroom, two full bath, centrally air conditioned home that sleeps up to 11 people with 1 queen, 2 full beds, two twin beds, 4 twin bunk beds, 1 pullout couch and is located within driving distance to Chincoteague island(10 miles) and NASA(4 miles). This home offers a spacious kitchen, large Master Bedroom and living room that opens into a patio with gas grill and fire pit. This home is secluded, bright, cheerful, spacious and is the perfect spot for some much needed rest, privacy and relaxation. From the moment you enter you will feel comfortable and right at home. This home has a NO PETS and NO SMOKING policy. A washer/dryer is provided for your convenience.Ray's Shanty popular seafood restaurant is in walking distance.

Located in Chincoteague, Virginia, United States. WATERFRONT 4 BR family friendly home: Fun game room, Private yard with fire pit Property updated March of 2023. Welcome to Coastal Pines! A Relaxing and private single home located directly on the bay canal. This home has 4BR and 3.5BA. Bay views from every room! 1st floor:This home is elevated- stairs are required to access the main floor. Relaxing 1st floor bedroom with a king-sized bed private full bath including separate shower and bathtub. Coffee bar (k-cups). Enjoy your coffee on the private deck overlooking the backyard and canal. LED cable TV. Pack n play will be available and located in this closet.A full-functioning updated kitchen with everything you need to cook meals or host a gathering with an island that seats 2. Large dining table with seating for 10. Behind the couch is a wide console table which seats an additional 4. Highchair included.LARGE sectional sofa to fit your whole group in the family room which includes a gas, stone fireplace. Enjoy meals or just relax on

Located in Chincoteague, Virginia, United States. Sunset Bay 307 - Gorgeous Bay Views and Pool! Sunset Bay 307 - Sometimes you just have to go with the Waves…..Welcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop and dine in the Historic District. Picasso offers the Luxury you want, the Amenities you need, and even a Pool, all at a family-friendly price! There's even a Private Boat Slip - Boats must be 20 ft. or less. As you enter this lovely Condo, you’ll be greeted by warm Colors of Sand with fun pops of Nautical Reds throughout .This lovely 3 Bedroom Waterfront Condo sleeps 6 in 3 Bedrooms, in both comfort and style. The open layout is perfect for spending time with those who

Located in Chincoteague, Virginia, United States. Deer Track-Close to town-Firepit! Cozy cottage in a tranquil setting, designed for optimum vacation comfort.Quiet - yet a short walk to downtown.Larger Bedroom with a queen, another with bunks. Shared BathPrivate screened porch.Deer Track has a comfortable layout for a family vacation.

Located in Chincoteague, Virginia, United States. Pine Island Retreat Waterview Island home has 3BR's, 1st & 2nd level porches Amenities: C/A, Microwave, W/D, 3 Screened Porches, Charcoal Grill, W/D, WiFi, Smart TV, Pet Friendly,Step back in time in this traditional island home loaded with character and 3 screened porches! Tucked back off Eastside Drive this private setting is a perfect spot to unwind. Have your morning coffee on the second level porch with distance lighthouse views or dinner and drinks on the large screen porch off the kitchen. This home rents by the week only.Call office for rates. Please ask about our cancelation policy. 60 day cancellation prior to occupancy date (100% refund minus processing fee, travel insurance and credit card fee's). Pet friendly home $75. per pet fee will be added to your reservation.Bed Sizes: 1 Queen, 1 Double, 3 Twin Sleeps 7Saturday Change Over Day$ 107- 220 Nightly plus tax & fees**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charg

Located in Chincoteague, Virginia, United States. Meme's Landing-Charming 4-bedroom house in welcoming Chincoteague Dock your boat or go crabbing along the private bulkheaded shoreline. A large screened porch, is perfect for gathering with the family.Spacious living room, fully equipped kitchen, and a dining room.2 Kayaks and Cornhole boards are provided.There is also a sunroom with a queen sleeper sofa which provides a 4th private sleeping area.

Located in Chincoteague Island, Virginia, United States. Carriage House on Chincoteague - Sleeps 12 and Pet Friendly! Carriage House - Relax, Rejuvenate, and Reconnect……The best things in Life are the people you love, the places you go, and the Memories you make! If you’ve been looking for that special place to make incredible Vacation Memories, you’re going to fall in love with beautiful Carriage House in Oyster Bay II! AND, your family dog (2 max) is welcome with a $100 Pet Fee each, so no one is left behind on this Family Vacation!Carriage House is like a Southern Living breath of fresh air - easy, breezy, and beachy. Tucked on a super quiet street on the Northside of our Little Island by the Sea, you’ll be close to everywhere you want to be, but feel a million miles away from the real world. Oozing Southern Charm and hospitality, and adorned in bold red and crisp white, the Front Porch beckons you to sit a spell and sip Sweet Tea. Y’all are never going to want to leave Carriage House….The Living Area is sure to be the heart of your famil

Located in Greenbackville, Virginia, United States. Octopus's Garden - Gorgeous Waterfront in Captain's Cove! Octopus’s Garden - “I’d like to be under the Sea ~ in an Octopus’s Garden in the shade!”When was the last time your Vacation took your breath away? If that is what you’ve been yearning for, clear your schedule - Paradise awaits you in beautiful Captain’s Cove Golf and Yacht Club! Tucked Canalfront on a quiet cul-de-sac, it’s the perfect place to kick back and relax. Take in that salty, sweet bay breeze as you relax on the Deck with gorgeous Views of both the Canal and the Chincoteague Bay. Just imagine fishing and crabbing right in your own backyard - and don’t forget to bring the Boat! Drop it in at the Cove’s Marina, and the house is just around the bend. Octopus’s Garden is all about waterfront living at its very finest. What’s even better? This fabulous Home is part of our Flex-Stay Program with only a 3 night minimum all year!Captain’s Cove is one of the Best Kept Secrets on the Eastern Shore of Virginia! Captain’s Cove is