358,603 properties available

Located in Chincoteague, Virginia, United States. Newly renovated water view cottage nestled in the pines. Newly renovated charming two bedroom one bath cottage on Chincoteague Island, Virginia. This cottage features an open living and kitchen area with cathedral ceilings, and a large private yard. Breathtaking views of Sheepshead creek and all the waterfowl that call it home. You will be just minutes from the beach and just steps from the water. The Assateague light house is viewable from the property as well as all the wildlife that Chincoteague Island has to offer. This property is only a two minute walk to kayak rentals. We are sure you will enjoy your stay at our secluded little piece of paradise!

Located in Chincoteague Island, Virginia, United States. Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard Great Waterview location on Chincoteague Island overlooking the Assateague Channel, the lighthouse and the marsh where the wild ponies graze. Three large bedrooms and 2 baths. Only 5 minutes to the beach or 3 minutes to town.The bedding situation is as follows:-Downstairs bedroom: queen-Upstairs rear bedroom: queen-Upstairs front bedroom: doublefull plus a set of twin bunks-Additional queen futon in the downstairs greatroom.

Located in Chincoteague Island, Virginia, United States. Saltwater Pony on Chincoteague Island! Welcome to Saltwater Pony - Beach Mode activated!Have you been longing for a Beach Vacation that is truly easy-breezy? Clear your calendar and grab those who matter most, because we’ve got you covered with this gorgeous Custom Home in the very heart of Chincoteague Island! Saltwater Pony is tucked on Ridge Road - close to everywhere you want to be - including in the path of the Pony Parade during our Annual Pony Swim - and is almost Brand New! Only a few minutes from Assateague National Seashore, where our famous Wild Ponies roam free, there’s so much to do. Whether you enjoy fishing and crabbing, sunbathing, or shell-combing, you’re sure to find our slice of heaven to be pure paradise!As you pull up to Saltwater Pony, you’re welcomed by its charming Coastal Style - the Covered Porch beckons you to sit a spell and sip Sweet Tea, as you watch our Little Island by the Sea come to life each morning. With plenty of parking and all the bells and whistl

Located in Chincoteague Island, Virginia, United States. Rhythm and Blues, a beautiful 3 Bedroom/2 Bath home located in the heart of our Rhythm and Blues - The Ocean's Roar is Music to the Soul..... You know that favorite song that just stays with you - the one you long to hear again and again? This is the feeling you will get while staying at Rhythm & Blues on beautiful Chincoteague Island. Tucked away on the East Side, this Charming Chalet will steal your heart. Located only steps from the Public Boat Launch & amazing Views of the Assateague Lighthouse, Rhythm & Blues is the perfect place for kayakers, boaters, & nature lovers. As you turn down Pointer Lane and see Rhythm & Blues nestled in the whispering Pines, you'll know you're in for a very special Vacation Experience. Traveling with a large family or several families together? Be sure to check out her Sister House, Les Bon Temps, right next door - the perfect way to have lots of togetherness, while still having privacy. Park the car and leave your worries at the end of the quaint b

Located in Chincoteague, Virginia, United States. A stunning 3 Bedroom Waterfront Dream Condo that even allows your Family Dog! Sunset Bay Villa 209...Travel is the only thing you buy, that makes you richer..... SUNDAY CHECK-IN DURING PEAK SEASON 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, Drawbridge, & the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons & Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop & dine in the Historic District. Sunset Bay Villa 209 offers the Luxury you want, the Amenities you need, all at a family-friendly price - and life is always a little happier when the family dog can come along! Sunset Bay Villa 209 just screams 'Luxury Vacation' - upon entering, you'll fall in love with the Serene Colors of Sand & Sky. Both refreshing and relaxing, you'll know what a special place this is - a Tropical Oa

Located in Chincoteague, Virginia, United States. Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies! Cozy cottage. Relax and enjoy! Walk the charming streets. Friendly town. Walk to restaurants, shops and activities. Local artisan/ farmers market is on the same street every Wednesday and Saturday from April through October! Pick up pickleball courts nearby - both outdoor and indoor courts. Brianna’s park next door. Fantastic children’s playground across the yard! Must try the red barbecue food truck within walking distance! Main Street shops and restaurants flat and easy walking! Pick up the trolley on Main Street! Dollar store, pharmacy, post office and grocery store are all easy walks from the house. Walk to shops and restaurants on Maddox as well! For fitness lovers:Outdoor basketball court; fitness equipment, picnic tables and soccer field across parking lot. May 4th 54th Annual Seafood Festival

Located in Chincoteague, Virginia, United States. Lily Pad on Chincoteague Island - Lighthouse Views and Pet Friendly! Lily Pad on beautiful Chincoteague Island is the perfect place to make your Vacation Dreams come true. This adorable and affordable Vacation Home is located on the ever-popular East Side, tucked on a quiet street, yet super close to everywhere you long to be. Lily Pad will greet you with an inviting yard and lots of parking for your cars and water toys. This charming Home sleeps 6 at a very family-friendly price tag. Once you sink into an Adirondack Chair around the Fire Pit and see the breathtaking Views of Assateague Lighthouse, you'll never want to leave! Relax in the Living Area after an adventurous day exploring Assateague National Seashore, and enjoy the comfort of AC, Flat Screen Streaming TV, and Free WiFi. With the quintessential Island Charm you love and the Modern Amenities you need, Lily Pad is sure to please the whole family.The Chef in your family will love the well-stocked Eat-in Kitchen with everything

Located in Chincoteague Island, Virginia, United States. A Shore Joy - Private Pool - Waterfront with Pier! “The Ocean stirs the heart, inspires the imagination, and brings eternal Joy to the Soul.” ~ R. WylandWhen was the last time you experienced the pure Joy of time spent with those who matter most - away from all the distractions of our daily lives? Work, school, chores, homework - the hamster wheel seems to never stop spinning. It’s more important now than ever to jump off that wheel - grab your calendar, and let us help you plan something truly magical for your family.A Shore Joy is just that - pure magic! This breathtaking one-of-a-kind Bayfront Home sits on South Main Street, in the very heart of our Little Island by the Sea, and faces the most incredible Sunsets and Bay Views you may ever see. If you want it ALL, this is the place for you. A Shore Joy oozes that quintessential Chincoteague Charm you love, and has the Modern Amenities you want and need - plus a Private Pool! It also happens to be close to the Chincoteague Carnival Gr

Located in Chincoteague, Virginia, United States. Misty Manor - 3BR home, tucked away, sc. porch & pet friendly. 1st level BR. Amenities: Central A/C, W/D, Dishwasher, Microwave, 2 TVs, WiFi, DVD, Screened Porch, PETS UNDER 40 LBS ONLYThis bright and cheerful home is tucked away on a private lane next to the historic Misty's Pony Farm. With a quiet location and a spacious screened back porch, this house is perfect if you want to relax in nature but still be close to downtown. It offers a first floor bedroom and bath. Close to Summer Memories. Now offering WiFi.. 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). This Property accepts pets under 40 Lbs Only***Bed Sizes: 1 Queen, 1 Double, 2 Twin, 1 FutonSunday Change Over$ 108- 190 Nightly plus tax & fees**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Located in Chincoteague, Virginia, United States. Chincoteague Townhome w/ Pony Views from Deck! Let your worries float away in the bay as you relax at this 2-bedroom, 1.5-bath vacation rental home! This space is an equine dream with direct views of the wild horses on Assateague Island - a view that takes your breath away. If you're not here for the annual Pony Swim, you'll find Chincoteague Island brimming with activities; from fishing to crabbing, heritage tours, horseback riding and more. You'll soon see why it's so easy to fall in love with a little island like this!-- THE PROPERTY --**Please note that linens and towels are not provided. It is recommended you supply your own (pillows, and blankets will be provided)**Bedroom 1: King Bed | Bedroom 2: Twin/Full Bunk Bed, Twin Bed | Living Room: Queen Sleeper Sofa Start each early morning on the private deck, with a warm cup of coffee and a tranquil atmosphere all around. Perched high above the town on the third-story, this deck poses as a front-row spot to see the wild horses gallopi

Located in Chincoteague, Virginia, United States. Goose Bay - Water View - Pet Friendly - Screened Porch - OS Shower - Grill Amenities: Central A/C, Microwave, Direct TV, 2 TVs, DVD, Dishwasher, W/D, Fireplace, WiFi, Charcoal Grill, Outside Shower, Deck, Screen PorchGoose Bay tucked away off the northern end of Main Street offers a tranquil and serene location with outstanding water views and sunsets over the Chincoteague Bay and ponds. First Floor bedroom and two additional bedrooms with loft/sitting area on the second level. Very stylish 3 bedroom, 3 bath home with views and decks from almost every room. This home is also pet friendly and next door is Goose Bay's sister home, A Summer Place (sleeps 10) which offers a great location for family groups or reunions.. 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) will be added to your reservation.Bed Sizes: 2 Queens, 1 Double, 1 Twin,

Located in Chincoteague, Virginia, United States. Salty Sailor - 2BR cottage close to Memorial Park & launch area Pet friendly New Rental ! More Photos and information coming soon. Cozy pet friendly cottage, with 2 bedroom and 1 bath. Each bedroom has a queen size bed and queen sleeper sofa in living room. Within walking distance to Memorial Park and boat launch. Please ask about our cancelation policy. 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) will be added to your reservation. ***This Property accepts Small and Medium Dogs Only***Bed Sizes: 2Q, QSSSaturday Change Over $ 97-155 Nightly plus tax & fees**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Located in Chincoteague Island, Virginia, United States. Vast Views - Pet friendly; Shared pool! Discover the charm of island life in this delightful townhome, perfectly positioned for both relaxation and adventure! This two-bedroom, 2.5-bathroom home offers a fresh and modern layout with many new upgrades for 2024. Each bedroom is thoughtfully designed with comfort in mind, including a spacious primary suite with its own private bathroom. The second bedroom features a twin-over-full bunk bed. Both bedrooms, in addition to the living room, have flat-screen Smart TVs. The fully equipped kitchen caters to all your culinary needs whether you are preparing a quick snack or hosting a dinner party.Step outside to enjoy exclusive community amenities like a swimming pool and a pier with direct water access to the scenic Assateague Channel. Try your hand at fishing or crabbing, or tie up your boat from one of the nearby boat rental shops. Plus, there's no better way to end your day than with mesmerizing water and lighthouse views right from your vaca

Located in Chincoteague Island, Virginia, United States. Sunset Bay 216 - Luxurious Waterfront with a Pool! 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, 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. Sunset Bay Villa 216, aka ‘Captain’s Quarters’, offers the Luxury you want and the Amenities you need, all with a family-friendly price tag!Captain’s Quarters is the perfect blend of Luxury Vacation and Casual Coastal Getaway. This 2nd Floor Condo is situated such that it directly faces our famous Chincoteague Sunsets - and I promise, they do not disappoint. There is also a convenient Elevator and Ramp if stairs aren’t desirable. As you enter Captain’s Quarters, you feel instantly relaxed - kick off those flip flops and say hell

Located in Chincoteague, Virginia, United States. Bayside and Beyond - Sunset Bay Villa 105- Waterfront Just Listed!Stylish comfort, sunset views, and pool with this nicely decorated condoIst Floor Unit with Private Boat SlipThe master king bedroom enjoys waterfront views and shares deck access with the living room.Fabulous Master bath features jetted tub, separate large shower stall and double sinks.The queen bedroom and 2 doubles bedroom share adjoining hall bath.Great fitness room next to the pool area.No better spot on the island for sunset views.

Located in Chincoteague, Virginia, United States. Bertie Street Cottage on Chincoteague Island! Life takes us down many paths, but our favorite ones lead to the Beach. Looking for the perfect Island getaway for your family? Welcome to Bertie Street Cottage - adorable and affordable in the heart of the Island. Located in a peaceful, quiet part of our wonderful Island, you'll enjoy the serenity here after a busy day of exploring Assateague Island. Close to everywhere you want to be, with the feeling of being a million miles away.....Bertie Street Cottage has had many updates this Fall and has a fresh new look! You'll love relaxing in the cheerful Living Room with hues of Sea Grass Green punctuated with bright pops of reds and blues. Such a great place to gather and share stories of the day's adventures, or perhaps enjoy family movie time on the Flat Screen Streaming Only TV, and of course there's Free WiFi!We are just in love with the Screened Porch at Bertie Street Cottage - beautifully furnished, you'll feel as if you're on a Tropical

Located in Chincoteague Island, Virginia, United States. Kelly's Cottage - In town, kayaks included! Take a look at this adorable, modest cottage! Kelly's Cottage is conveniently located close to town, where you will find plenty of shops, dining and beautiful water views. Enjoy your vacation getaway at Kelly's Cottage while sitting on the sunporch and enjoying your morning coffee, or snuggle up in the living room with some popcorn and a movie. The kitchen offers everything you will need to prepare meals for the week, or order out from one of the wonderful restaurants our beautiful Island has to offer. You will find all 3 bedrooms upstairs and a full bath downstairs. Outside there is a charcoal grill and a large yard for your enjoyment. Kelly's Cottage also offers bikes, a kayak, and beach chairs!- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!- No smoking is permitted on the premises. - No pets are permitted on the premises.- Any reservations made for a future year (known a

Located in Greenbackville, Virginia, United States. Off Duty - Pet Friendly, Waterfront! NEW FOR 2023!! New vinyl plank floor downstairs, new furniture, and paint throughout, new decking, kitchen island, outdoor shower, and tiki bar addition downstairs! Off Duty offers 3 bedrooms, 2 bathrooms, a large screened porch, front deck with bay views, and a large outdoor space for your enjoyment. Bring your fur babies along, because this home is pet friendly! Upon entering the home, you will find yourself in awe of the large open floor plan, boasting high ceilings and tons of waterfront views for your enjoyment. Downstairs you will find two bedrooms, one with a queen sized bed and deck, as well as a bedroom that has a full sized bed and a twin bunk bed. Upstairs is an additional bedroom with a queen bed and full bath, along with a sitting area looking over the downstairs living space. Don't feel like sitting inside? Go out to the large screened in porch and enjoy the sounds of nature, or sit downstairs under the home one afternoon and enjoy s

Located in Greenbackville, Virginia, United States. Serenity Now - 20 minutes to Chincoteague! Serenity Now -  It's exactly what you need!Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept secrets on the Eastern Shore of Virginia! This spectacular Vacation Home will make all your dreams come true with something for everyone in the family. Located directly on the Chincoteague Bay, this home is only 25 short minutes by car or boat to Chincoteague and Assateague Islands, where our wild ponies roam free. Looking for some OC excitement? Ocean City, MD is a short 45 minute drive away. As you drive down Blackbeard Road, it’s hard to keep your eyes on the road - you’ll want to stare at the Bay, only steps away. You cannot wait to see where you’ll be spending your ESVA vacation. As you come around the bend and see this gorgeous home, you know you made the right choice. The first thing you will notice is ample parking for 4 cars, and a double garage perfect for storing all your toys, kayaks, beach chairs, and more.Upon en

Located in Chincoteague Island, Virginia, United States. Cozy Nest - Waterview, Pet Friendly, Screened Porch Welcome to "Cozy Nest," a charming home available for your next vacation experience, offering an idyllic retreat with stunning water views! This inviting property spanning over 900 sq. feet can accommodate up to 6 guests, making it an ideal choice for families, friends, or anyone looking to immerse themselves in comfort and tranquility. "Cozy Nest" features two well-appointed bedrooms and two full bathrooms, ensuring privacy and convenience. The primary suite bedroom, encompassing the entire second floor, offers a peaceful haven for relaxation with its serene views, private bath, and private deck access. The first floor provides flexible sleeping arrangements with two twin beds in the bedroom, and a sleeper sofa in the living room. The full bath on the first floor rounds out the convenient layout. The heart of this home is its beautiful outdoor spaces. A screened porch provides a bug-free zone to enjoy the fresh air and scenic surroun

Located in Chincoteague Island, Virginia, United States. Charming Chincoteague getaway, short walk to the fair grounds and pony penning Rest A' Shored is a brand new home (2019) with a sweeping, open floor plan that can comfortably accommodate two families with children or three couples for your island retreat. Located on willow street, the property is just a short walk to Main street and the Chincoteague Fair Grounds, right in the heart of the pony penning action! The house provides all the modern amenities needed for your stay with a touch of Chincoteague charm. The kitchen is well equip with everything you need to cook for a crowd! Granite counters, 2 refrigerators, dishwasher, plenty of pots, pans, serving utensils, crockpot, electric griddle, even a blender for all those mixed drinks! Enjoy family meals at the dining room table which comfortably seats 8, plus an additional 5 at the bar top on the kitchen island. A large screened in porch can accommodate all your guests to enjoy meals outdoors, or relax with a cocktail and feel the co

Located in Greenbackville, Virginia, United States. Bayview - Game Room, Waterfront, Pools! Experience the perfect blend of comfort and convenience at "Bayview"! Perfect for families or anyone needing space, this property features four well-appointed bedrooms and two and a half bathrooms, all located on a picturesque canal in the amenity-rich Captain's Cove community!Step inside to find a welcoming living room leading into a cozy sitting area—ideal for relaxing evenings. The home's standout feature is a large covered porch where you can enjoy stunning waterfront views of the bay, making it the perfect spot to unwind or entertain guests. Beyond that, there's an inviting open deck that offers a serene setting for outdoor meals or starlit gatherings.Active and spirited family members will delight in the game room equipped with foosball and shuffleboard tables for endless hours of fun. The house also includes a practical den that doubles as an additional sleeping area, ensuring comfort for all guests.Community amenities add to the appeal wi

Located in Chincoteague Island, Virginia, United States. Beach Breeze - Charming cottage; Close to town! Welcome to "Beach Breeze"! This tastefully adorned vacation rental is a single story rancher home that has undergone major renovations, with all new fixtures and furnishings throughout! Traveling with pets? The four-legged family members are welcome here! Conveniently located on a side-street just off of Bunting Road (and a very short distance to Main Street), you'll enjoy being close to the carnival, movie theater, downtown restaurants, shopping and more! Come and check out this simple, clean and affordable beach retreat. You won't be disappointed!- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!- No smoking is permitted on the premises. - 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.- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability

Located in Pocomoke City, Maryland, United States. Spectacular Waterfront on the Pocomoke River! “A good River is Nature’s life work in song….”The sound of the breeze rustling through the trees. The smell of a campfire on the banks of the River. The sight of the pristine Pocomoke River flowing by - floating all the worries of the real world away. Does that sound like an amazing getaway to you? It’s everything we love about camping, yet in a Luxurious Custom Vacation Home. How can you beat that?!Casa Del Rio is an incredibly unique Vacation Experience just 30 minutes from Chincoteague Island, where our famous Wild Ponies run free, and 45 minutes away from action-packed Ocean City, Maryland. Yet with the beauty and Amenities at this lovely home, you may not want to go anywhere else! The Pocomoke River stretches 66 miles from Southern Delaware through Southeastern Maryland. Teeming with wildlife, it’s the deepest water for its width in the entire United States, and the 2nd deepest in the world - 2nd only to the Nile River! And yes, it’s r