358,603 properties available

Located in Chincoteague Island, Virginia, United States. We’ve Thought of Everything So You Can Relax! Relax and enjoy nature in our home with a light and airy coastal feel in every room. Get away from the sights and sounds of traffic and city chaos in our private, secluded cul-de-sac location. Take a peek at the water through the trees from our private, second floor deck. Listen to the song birds, ducks, toads and frogs all flourishing in the undeveloped lots surrounding our property.A short walk away - Historic Downtown & Island CreameryRecently upgraded entire HVAC system, which now includes both a Carrier electronic air purifier and a Remi Halo LED purifier to further protect our guests’ health while also ensuring their comfort in the home. Pack-n-Play (portable crib) and high chair available for your convenience. Kitchen is fully stocked with stoneware dinnerware, dishwasher, and four burner dual oven stove, as well as a fully stocked spice cabinet. Additionally, there is a large outdoor gas grill with side burner. Beach chairs, ski

Located in Chincoteague, Virginia, United States. Shucker's Tump - 3BR pet friendly home close to town. Lg screened in porch. 3BR/2B***(Single Level Home) {2Q, 1Bunk w/2T} Amenities: Central A/C, Microwave, Cable, WiFi, W/D, Screen Porch, Deck, Barbeque Grill, Outside Shower, Handicap Accessible with a ramp and handicap shower. A $75.00 pet fee per dog will be added to your RSVPAmenities: Central A/C, Microwave, Cable, WiFi, W/D, Screen Porch, Deck, Gas Grill, Outside Shower, Handicap Accessible with a ramp and handicap shower.Shuckers Tump is a pet friendly home, located in town within walking distance to shops and restaurants. Handicap Accessible with a ramp and handicap shower. Formerly known as "Cowboy Cottage". This home is open and bright with easy access to all island attractions. 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 Dogs Only (limit 2)Bed Sizes: 2 Queens, 1 Bunk Bed w/2 TwinsSunda

Located in Chincoteague Island, Virginia, United States. Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se Happy Pines - Refresh, Renew, & Reconnect As you turn onto Pine Creek Drive, you will feel the hustle & bustle of the busy world melt away. Happy Pines is located near the end of this quiet street, nestled in a Pine Grove, and surrounded by beautiful trees and Beach Grasses. This lovely 3 Bedroom, 2 Bath Vacation Home is in THE perfect place - walking distance to the famous Carnival Grounds and everywhere you want to be, yet you will feel a million miles away. It is a wonderful combination of convenience and serenity. With a layout suitable for one family or two small families, this awesome home is definitely the place to be for your Chincoteague Island Vacation. The warm and inviting Living Area with Gleaming Floors, Cozy Fireplace, Free WiFi, and huge Flat Screen Cable HDTV is a wonderful place to relax after a day of exploring the Beach and Assateague Island. Sink into the oversized, comfy furniture a

Located in Chincoteague, Virginia, United States. Saltwater Cottage - Pet Friendly! Welcome to beautiful Saltwater Cottage, in the heart of Chincoteague Island, Virginia. You've heard stories about our little piece of Paradise - the Wild Ponies running free, Saltwater Cowboys leading the way, the Saltiest, Sweetest Oysters to be found, and hands down THE best Sunsets over the water. Guess what? It's ALL true - isn't it time you discover this incredble Vacation Destination?!  This adorable Cottage is located on Anderton, just off of Church Street - a super short stroll to Main Street, where many Shops and Restaurants are located, as well as Robert Reed Waterfront Park - a fabulous place to take in one of our famous Sunsets! As you enter the Cottage, you'll know you made the right choice. Beautifully decorated with a tasteful Coastal Flair, the soothing Colors of Sand & Sea are both serene and refreshing. Relax in the spacious Living Area after a fun-filled day on the Beach and enjoy the Free WiFi and Flat Screen TV with Streaming. With

Located in Chincoteague Island, Virginia, United States. 3 Bedroom House with adjoining small hosts apartment, may/may not be occupied Watch the saltwater cowboys ride out on the morning of pony penning from the front porch. ** located in about 1 mile from the town center** Shared laundry** Master Bedroom includes full bath with queen size bed** Bedroom 2 features a full-size bed and a single mattress bunk** Bedroom 3 features 2 twin size bunk beds/sleeps 4** Two full bathrooms* Comfortably accommodates large groups * Fully stocked kitchen breakfast bar. * Living room provides a restful atmosphere with comfortable furnishings and appointments including a flat screen 55-inch TV, DVD player.* Smart TV with Amazon, Netflix, HBO Paramount subscription in addition to antenna.* Kitchen is the perfect place to enjoy family dinners and gather after a day at the beach.* Just off the kitchen is a sunroom and front screened porch 16 x 20 is the ideal spot to relish that morning cup of coffee. You will love the view of horses while relaxing in the co

Located in Chincoteague, Virginia, United States. Brant Creek Cottage-Single Family Home-Waterfront- Linens and Towels Provided Amenities: /4BR, 21/2 bath home. (2 bedrooms on 1st floor, each with Queen beds. 2nd level loft with 2 Twin Beds and sitting area. 2nd sleeping area with full bed. Heat and Air, Front Porch, Screen Porch, Waterfront, WIFI, TV, Linens and Towels Provided. Keurig coffee maker, starter gift pkg provided. 5 TV's. Charcoal grill. Brand new Construction and new for 2024 Rentals. This wonderful creek side home offers 2 owner suites on first level and Upstairs 2 additional sleeping rooms and sitting area, Bright beautiful great room with large dining area and great kitchen. Screen porch in the back and a Creekside view perfect for birding and other wildlife. Very quiet location tucked away location is central to Town and Beach Road. Linens and towels provided. RING Camera on Front Door. Please ask about our cancelation policy. 60 day cancellation prior to occupancy date (100% refund minus processing fee, trave

Located in Chincoteague Island, Virginia, United States. Shore Beats Work - Affordable and Great Location! Ready to kick back and enjoy a little “island time”? ‘Shore Beats Work’! If you’re looking for the perfect Home Base for your next Chincoteague Island Adventure, look no further than ‘Shore Beats Work’ in Eastwinds. Located in the very heart of Chincoteague Island, this lovely Townhome is convenient to everywhere you want to be on our beautiful Island, yet a quiet and peaceful Retreat at the day's end. Eastwinds is a small community of townhomes surrounded by Whispering Pine Trees just off of Church Street, which offers easy access to everything you love about our Island. Only minutes from the beach, downtown shops and restaurants, and more, it's Vacation Central, for sure! As you wander down the path to Shore Beats Work, you'll feel the serenity of the trees swaying in the salty air and that wonderful feeling of calmness that overtakes you when you realize you're finally HERE. This lovely home is warm and well appointed. As you ente

Located in Chincoteague, Virginia, United States. Spacious + Family-Friendly Home in Chincoteague! Escape to Chincoteague and make unforgettable memories at ‘My Happy Place.’ This charming 4-bedroom, 2-bathroom vacation rental features a seasonal pool and plenty of space for up to 14 people! Nestled near top attractions like the Chincoteague National Wildlife Refuge and Assateague Island, this home offers the perfect location for exploring the natural beauty of Virginia's Eastern Shore. Kick back on the deck, grill up a delicious dinner, or take a leisurely bike ride through the town.-- THE PROPERTY --2,961 Sq Ft | Private Backyard w/ Fire Pit | Kayaks + Bicycles | Seasonal Pool | 1 Mi to Waterfront ParkBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Bedroom 4: King Bed | Family Room: 2 Twin Beds w/ Twin Trundles, Queen Sleeper Sofa | Additional Sleeping: Toddler Bed, Pack ‘n Play, Bassinet/CribOUTDOOR LIVING: Furnished deck w/ outdoor dining, patio, gas grill, life vests, horseshoesINDOOR LIVING: Smart TVs w/ cable

Located in Greenbackville, Virginia, United States. Bliss by the Bay - Canal Front with fabulous Amenities! Bliss by the Bay - If you’re wearing flip flops, you’re overdressed!There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at Bliss by the Bay in beautiful Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly on the Chincoteague Bay, just 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. Here, life takes a slower pace - sipping wine as you watch the sun sink into the Chincoteague Bay, or the joy you feel watching the kids catch Crabs off the dock. THIS is what Vacation Dreams are made of.Bliss by the Bay has been a beloved Vacation Rental for several years, but is Brand New to our Seaside Vacations’ Family, and we couldn’t be more excited! Tucked directly on t

Located in Chincoteague Island, Virginia, United States. EVENTIDE on Chincoteague Island! “Travel is the only thing that leaves you speechless, then turns you into a storyteller.” ~ Ibn Battuta Have you been longing for a Vacation Experience that your family won’t soon forget?! Life is so busy - work, school, games, and meetings steal so much precious time from us. It’s so important to grab those who matter most, and just BE together. And boy, do we have the perfect place for you to reconnect, rejuvenate, and relax. Welcome to EVENTIDE on Chincoteague Island. This home away from home simply oozes Southern Charm and Hospitality - we are so in love with it! Tucked on a super quiet Lane on the ever-popular East Side of our Island, you’ll feel a million miles away from the hustle and bustle of the real world, yet close to everywhere you want to be. offering two new boat ramps so bring the boat - there's plenty of room in the driveway! In addition to boat ramps, Memorial Park provides a great spot to launch kayaks, fish and crab from the pier, en

Located in Chincoteague Island, Virginia, United States. Barefoot Breeze - A breath of fresh air! Life’s at ease with an Ocean Breeze……You know that feeling you get when you step onto the Beach for the first time each Summer? That first deep breath - the saltiness of the Sea, the scent of Coppertone, the sound of the Gulls - this is life at Barefoot Breeze on Chincoteague Island. It’s not just a Vacation Rental, it’s a Destination, an Experience, if you will. This amazing Home sits on the banks of a serene Pond in ever-popular Oyster Bay II in the heart of Chincoteague. This lovely Community is a fan-favorite with quiet streets perfect for walking or bike riding, lined with whispering pines. Barefoot Breeze is even more special sitting at the end of a quiet cul-de-sac, with a Pond right in your backyard. Barefoot Breeze is brand new to being a Vacation Home, and is beyond stunning. Dressed in Coastal Colors of Sea Grass and Bay Blue, it’s welcoming and relaxing. Kick off your Flip Flops in the Foyer, you’re on Island Time now…..As you wander

Located in Chincoteague Island, Virginia, United States. Seaside Rendezvous is a fabulous & newly renovated End-Unit Waterfront Townhome Seaside Rendezvous - Travel is the only thing you can buy that makes your richer..... Isn't it time for a new romance.....with Life?! A visit to fabulous Seaside Rendezvous is certainly the place to begin. This phenomenal End-Unit Townhome is located in a wonderful little community, Silver Sails. One of the most unique and wonderful features of this Neighborhood is that it has a spectacular Community Swimming Pool for you to enjoy after a day on the Beach! This is a rarity on Chincoteague Island and your family will love having this amenity! Silver Sails is tucked in the middle of Chincoteague Island, with easy access to everywhere you want to be! Seaside Rendezvous.....where to begin? This stunning 3 Bedroom/2.5 Bath Townhome has just been completely and beautifully renovated! Tucked away on a quiet, private cul-de-sac and backing to a gorgeous Tidal Creek, you will want to spend as much time outside a

Located in Chincoteague Island, Virginia, United States. Great White is a stately Victorian Vacation Rental that sleeps 12 in the heart o Great White - Memories made at the Beach last a Lifetime..... SUNDAY CHECK-IN DURING PEAK SEASON In Life, it's not where you go, but who you travel with. Family, Friends - those who mean the very most - are at times the hardest to get together. It's time - clear your calendar, grab those you love, and head to fabulous Chincoteague Island. If you make the time, we've got the place! Welcome to stately Great White - the perfect place to gather, reconnect, and relax. This gorgeous Historic Home is located on Main Street, only steps from Downtown Shops, Dining, and Robert Reed Waterfront Park - home of the best Sunsets to be found & Family-Friendly Free Events all Summer long! Besides the fact the Great White is an expansive Home that sleeps 12 and combines all you love about yesteryear with Modern Amenities, it also welcomes your Family Dog AND has Pool Access right next door at Sunset Bay Villas! Just imagi

Located in Chincoteague Island, Virginia, United States. The Robinson Family Beach House on Chincoteague! There is no time to be bored in a world as beautiful as this….Welcome to The Robinson Family Beach House on our little slice of Heaven, Chincoteague Island. Located on ever-popular North Main, you'll enjoy the peace and quiet, yet still be close to everywhere you want to be. The Attractions of Historic Main Street with so many quaint Shops and Restaurants, Robert Reed Waterfront Park, and the Chincoteague Carnival Grounds are just a short drive away, as is the Beach and attractions on Maddox Boulevard - the Beach Road. With 3 inviting Bedrooms and 2.5 Baths, this charming Home is ready to make your family's Vacation Dreams come true!After a fun-filled day exploring Assateague National Seashore and searching for our Famous Wild Ponies, you'll love coming back to the comfort of a true home, not a hotel room, with all the comforts of home. Rinse off in the Outdoor Shower, and relax in the comfortable Living Room and enjoy Flat Screen Stream

Located in Chincoteague Island, Virginia, United States. Sand Penny - Take in lovely Bay Views from this Chincoteague Island Duplex! Time spent at the Beach is never wasted…..What is it they say about finding a penny? It brings you good luck - good mojo, happy times! You’ll feel even luckier after spending some quality time with those who matter most at charming Sand Penny on beautiful Chincoteague Island. Tucked away in a quiet location just off ever-popular South Main, Sand Penny has all the makings of a Vacation you’ll treasure…..As you pull down the Lane to Sand Penny, you’re already dreaming of time spent at Assateague National Seashore, just a short drive away. Whether you enjoy searching for our famous Wild Ponies, Beach Combing, or just chillaxing, we have one of the most gorgeous beaches in our country. Did you know that Assateague National Seashore is the most visited National Park in our country? Spend a little time here and you will discover why this is.....Sand Penny offers plenty of Parking, and a great shaded Picnic Area right

Located in Chincoteague Island, Virginia, United States. June's Retreat - Waterfront; Boat dock! 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!​​​​​​​- 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

Located in Chincoteague, Virginia, United States. Egrets Landing-Beautiful Waterfront Cottage w/ Firepit, Kayak & Paddleboards! Spectacular views of Chincoteague Bay await you!Completely renovated and updated for the 2024 season (more pictures coming soon).Beautifully landscaped for your enjoyment.Relax while watching the sunset at the waterside fire pit.Kayak and 2 paddle boards provided.First-floor Features:Fully equipped kitchen, dining area, and cozy living room.Queen bedroom and full bathroom in hallSecond-floor Features:The first bedroom has a Pyramid bunk (twin over queen),The second bedroom has a queen bed.Shared full bath in hallwayPictures will be added mid January when work is complete.

Located in Chincoteague, Virginia, United States. Beechnut Villa-Waterfront-Cozy Waterfront duplex offers some of the best views of Assateague Island and the Lighthouse.Enjoy amazing views from the screened porch, which spans the entire first level.Spacious main level open floor plan.Room for the whole family to enjoy meals around the large dining table.Fully stocked kitchen, half bath, and living room with great views.First floor king and twin bedroom has a private full bathroom.Two additional bedrooms on second level share the full bath in hall.The rear bedroom has 2 twin beds.The front bedroom has a full bed, a twin sleeper, and private access to a second screened porch.AT THIS TIME, THE DOCK/PIER FOR THIS PROPERTY IS UNUSABLE AND CANNOT BE ACCESSED.

Located in Chincoteague Island, Virginia, United States. Heron Landing - In town; Coastal Cottage! Three words : Charming. Coastal. Cottage. Located just off of Ridge Road, in the center of the island, you'll find this adorable abode. 'Heron Landing' is newly remodeled. Downstairs you'll find an open floor plan with a fully equipped kitchen - with range, refrigerator, and dishwasher. A breakfast bar to enjoy a quick bite before you head to the beach. A comfortable and cozy living area with television. A half bath and washer and dryer can also be found downstairs for your convenience as well. A small porch with sliding door is located off of the living room, allowing you to crack open to let in the island breezes flowing over Assateague Channel. Upstairs you'll find the two bedrooms, both with queen beds. Beautiful, rustic, nautical themed decor. A full bath with tub/shower is also located upstairs as well. Enjoy your cup of coffee or cocktail on the cute patio area outside, or just to get a little extra island sunshine. Memorial Park is an e

Located in Chincoteague, Virginia, United States. WATERFRONT RELAXATION AT IT FINEST! Rachel's Retreat is Waterfront Relaxation at its finest, with gorgeous views of sunsets, balcony to enjoy the cool salt breezes, and a Master Bedroom and Living Room overlooking the waterfront. This beautiful, 2 bedroom, 2 bath, with private den, central air conditioned villa sleeps up to 6 people with 1 King, 1 Queen, and 1 Queen Sleeper Sofa (in den). A Pack -and-Play is provided for our small guests. Open kitchen and living room allows for easy family gatherings and dinners. The kitchen is furnished with range, refrigerator, microwave, dishwasher, toaster, coffee pot and grinder, Keurig Coffee Maker, blender, pots and pans, dishes, silverware and much more. Spend quality time together relaxing around the pool, strolling through town, exercising in the onsite fitness room, or just relaxing and watching TV together. You will find 3 Televisions in the home, one in the living room with DVD player, one in the master bedroom, and one located in the priv

Located in Chincoteague, Virginia, United States. Your Memorable Island Vacation Starts Where the Sidewalk Ends! Sidewalk's End is an adorable, 2 bedroom, 1 1/2 bath, central air conditioned cottage located in town for summer evenings spent strolling, shopping, playing miniature golf, exploring the many restaurants, and of course the ice cream parlors. The Comfortable living room with plenty of seating, is the perfect place to unwind and relax while watching TV. The kitchen is furnished with stove, refrigerator, microwave, pots and pans, dishes, crock pot, glasses, utensils and much more. This home also offers a Spacious Master Bedroom with 1/2 bath, 2nd bedroom with 2 twin beds and a full bath. The Large back yard is the perfect spot for family picnics, and gatherings, and you will even find a picnic table, and outdoor shower. Your Memorable Island Vacation starts where the Sidewalk Ends! This home has a NO SMOKING and NO PETS policy. We ask that you bring your own sheets (2 Queen, 2 Twin), and towels. A washer and dryer is provided

Located in Greenbackville, Virginia, United States. Sun Rayes - Pet friendly; Waterfront w/ Boat dock! We welcome "Sun Rayes"! What does this fabulous home have to offer? The question is: what doesn't it offer?! With 4 bedrooms, 3 bathrooms, 3 stories (with an elevator), a game room (ping pong, pool table, dart board, ring toss) and expansive decks - there's room for everyone! Situated on a canal in the popular Captain's Cove community, you have access to a boat ramp and you can dock your boat right outside your door! Also perfect for fishing, crabbing, kayaks, etc. Sun Rayes is packed full of fun - there are so many great spaces for entertaining and relaxing. The Captain's Cove community offers 3 pools (2 outdoor & 1 indoor), tiki bar, Marina Club and restaurant, 9-hole golf course, kids playground, dog park and more! (amenities are available for use with fee) And you're only 20 minutes from Chincoteague & Assateague Islands (the beach), and 30 minutes from Ocean City, MD (boardwalk & amusements).- No smoking is permitted on the premi

Located in Chincoteague, Virginia, United States. Bunting House - Water View - Single Family Home - Close to town - OS Shower Amenities:3BR/2B***(2B down/2BR 2nd floor/1BR 3rd floor) {1Q,1D, 2Q S/S, 1T S/S}. Central A/C, Microwave, Dishwasher, W/D, TV, VCR, DVD,WiFi, Cable, Gas Grill, Enclosed Porch, Outside ShowerSit back in the enclosed front porch and watch the sunset over the Chincoteague Channel! Located on South Main Street, this turn of the century Island home has been totally renovated with all the comforts of home. Large kitchen with stainless steal appliances and a gas range. Remodeled bathrooms with a stand up shower in one and a classic claw foot tub in the other. Both bathrooms are located downstairs and all the bedrooms are upstairs. Sit in the sun and enjoy family in the separate breakfast nook. With two living rooms, there is plenty of space to spread out.. 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)

Located in Chincoteague, Virginia, United States. Gorgeous Lighthouse Views right from the Pool! Think you can't have it ALL on your next Vacation? Think again - and check out fabulous Dancing Plover on Chincoteague Island! This gorgeous 3 Bedroom Towhome is located on the desirable East Side, only minutes from Assateague National Seashore. With a Community Pool, Dock, and a Family-Friendly Price Tag, Dancing Plover is the perfect Home Base for your next Island Getaway! Dancing Plover is decorated with a whimsical Coastal Flair, with beautiful Colors of Sand and Sea. Upon entering, soothing tans and sea glass blues are so inviting, and are stunning with the dark floors, reminiscent of a day on the Boardwalk. The Living Area is inviting with oversized comfy furniture, Flat Screen Streaming TV with Sling, and Free WiFi - the perfect place to relax after a fun-filled day at the Beach. The Kitchen and Dining Area are light and bright with fun Coastal Accents, Custom Glass Tile Back Splash, and the prettiest Starfish Pendant Light. Well-st