94,639 properties available

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

Located in Chincoteague, Virginia, United States. Grace Street Refuge-Beautiful VIEWS of the Chincoteague Bay, Firepit! Beautiful furnishings and superbly appointedDecks on each level afford beautiful sunset viewsPlenty of room for the entire family in this spacious homeBright and airy open floor planDouble handrails on all interior staircasesFirst Floor Features:3 season sunroom with pocket doors for privacyOpen, fully equipped kitchen with quartz countertopsDining area and spacious living roomOne bedroom with queen bed, second bedroom with twin trundleFull bathroom in hallway with Stander Security Pole & Curve Grab BarSecond Floor Features:Large master king bedroom features private deck with views of channel,cozy sitting area and deskSecond bedroom with queen bed and deskLarge shared bath with soaking tub, shower, and double vanity can be accessed from hall & king bedroomEnjoy garage room that includes games, table and foosballGarage access for storage and a 2nd fridge

Located in Chincoteague Island, Virginia, United States. Teal Cottage - Welcome to your Dream Vacation! Collect Memories, not things…..Life is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moments together that used to be easy to find, are hard to come by these days. This is why we must MAKE them happen! So, clear the calendar and grab those who matter most - we’ve got the Vacation of a lifetime for you right here on Chincoteague Island at beautiful Teal Cottage!Teal Cottage is the epitome of the Vacation Dream Home - gorgeous Coastal Colors and Decor, a fabulous Location perched on a serene Pond, beautifully Appointed, and you’ll even have Views of the Assateague Channel! Tucked at the end of a quiet street in ever-popular Oyster Bay II, this home truly has it all. And Oyster Bay II is a fan-favorite with quiet streets perfect for walking or bike riding, and is lined with whispering pines.Having made amazing memories here on our Little Island by the Sea themselves, the Owners of Teal Cottage named this special hom

Located in Chincoteague Island, Virginia, United States. The perfect Chincoteague Island Location and close to Pony Festivities! "Temenos is a Greek word used to designate a special place - a place of unique beauty - where you can go to separate yourself, to serve as a Retreat, a place for quiet Reflection, a place to recover your sacred center when the world is overwhelming." These words from the thoughtful Owners of this beautiful Home say it all - and encompass what we feel Chincoteague Island is all about.Located on South Main Street, Island Temenos in the heart of our charming Island, and close to everywhere you want to be. Take a short stroll to the Historic District for Dining and Shopping, catch one of our famous Sunsets at Robert Reed Waterfront Park, or do a little Fishing at the Community Pier. Enjoy gazing at our Wild Ponies next door at the Carnival Grounds next door as you relax on the Screened Porch, or wander next door for one of our famous Oyster Fritters while the Firemen's Carnival is there each weekend in July.Island Teme

Located in Chincoteague, Virginia, United States. Sailer Moon - Sunset & Waterviews! Renovated Victorian home with great views of Chincoteague Channel and Sunsets from the balcony.Screened porch, with a picnic table, is located off the kitchen at the rear of the house.The second floor features three bedrooms.One queen bedroom with balcony access and one with two twins, share an adjoining full bath.The third queen bedroom has access to the balcony for water & sunset views.Great third-floor attic space...It is a comfortable & private fourth sleeping area;featuring Double bed, TV & Half Bath.A second full bathroom is on first floor.

Located in Chincoteague, Virginia, United States. The Neigh-Neigh - Location! Location! Location! About this spaceNamed in honor of the ponies that first put Chincoteague on the map, this charming newly renovated family getaway is walking/biking/and wheeling distance to shops, galleries, restaurants, waterfront park, library and movie theater. Come relax in a stunning 2 BR, 2 full BA plus oversized upstairs den with queen and twin beds and a futon bed that comfortably sleeps 8. The amenities and unique offers this place has, is not to be missed.What this place offers:Unique in that linens and towels are provided for no extra charge!BathroomIroning board and ironBathtubHair dryerCleaning productsShampooConditionerBody soapOutdoor showerHot waterBedroom and laundryFree washer – In buildingFree dryer – In buildingEssentialsHangersRoom-darkening shadesHandheld Garment steamer and mini ironClothing storage: closetEntertainment:58” and 32” HDTVs with Roku and 43" Amazon Fire TV,Books, jigsaw puzzles, and specialty board games like Air Picti

Located in Chincoteague Island, Virginia, United States. Misty's Thicket - Water access; Screened porches! Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends. Upstairs, you find a great master bedroom with en-suite, a full bathroom off the hallway, and a second bedroom that features a bunk bed and a queen size bed that looks out onto the second-level screened in porch affording amazing Chincoteague Island views. - Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!- No smoking is permitted on the premises. - Pets are not permitted on the premises.- 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.

Located in Greenbackville, Virginia, United States. Calypso is a breathtaking Waterfront Vacation Home in Captain`s Cove. Calypso - Dance to the Song of the Sea..... You know that feeling you get while relaxing on the beach and listening to steel drums play while the Sea Breeze blows through your hair? Enjoy this feeling every day at fabulous Calypso in Captain's Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 4 Bedroom/3 Full and 2 Half Waterfront Dream Home has something for everyone in the family. Located Canal Front on the Chincoteague Bay, this statuesque home is a Water Lover's delight, and is only 20 short minutes by car or boat to Chincoteague & Assateague Islands, where our wild ponies roam free. Looking for some OC excitement? Ocean City, MD is a short 45 minute drive away. Have the best of everything, right in the heart of the Eastern Shore! Beautiful Calypso sleeps 8 more than comfortably. This Coastal Dream Home will take your breath away. As you drive through Captai

Located in Chincoteague Island, Virginia, United States. Pony View - Pet friendly; Waterfront w/ boat slip! Enjoy your cup of coffee as the sun peeks over the salt marshes of Assateague Island. You can often see a herd of our famous wild ponies grazing to the right of the lighthouse from your private waterfront deck and second-floor balcony - not to mention the copious amounts of waterfowl and other wildlife in the channel. Pony View boasts three bedrooms - A master with queen bed, full bath, and balcony on second floor, as well as another bedroom with a queen on the second floor - along with another full size bath. On the third floor you will find an amazing view of the marsh with the panoramic window and four twin beds, and a beautiful bathroom with a rustic wooden sliding door. The ground floor is where you'll find the hub of the house - fully equipped kitchen with refrigerator, electric range, dishwasher, and plenty of counter space. A dining table and bar seating area, a half bath, and a cozy living area with floor-to-ceiling knockout v

Located in Chincoteague Island, Virginia, United States. Lookout on Main - Your Waterfront Wonderland! Traveling - it leaves you speechless, then turns you into a storyteller….. And oh, the stories that newly renovated ‘Lookout on Main’ has in store for you! This one-of-a-kind Dream Home is located on South Main Street, directly facing THE most amazing Chincoteague Sunsets you could imagine. And you want waterfront, you say? It doesn’t get much more waterfront than at this fantastic home! Lookout on Main’s huge backyard is perched right on the banks of the Chincoteague Bay - 95 wonderful feet of shoreline with both a Dock and a Ladder. You can easily launch your kayak, canoe, or paddleboard right from the Dock, or bring your water shoes and do some clamming! Two kayaks and a canoe will be waiting for you to enjoy, as a matter of fact, along with crab pots, 2 boogie boards, and 4 beach chairs. In the evening, gather around the Fire Pit, sink into an Adirondack, and share stories of the day’s adventures - it doesn’t get much better than this….

Located in Chincoteague, Virginia, United States. ENJOY THE "BEAUTIFUL LAND ACROSS THE WATER" AT GINGOTEAGUE. Gingoteague, "Beautiful Land Across the Water", is a 4 bedroom, two full bath, central air conditioned home nestled within the heart of Chincoteague that sleeps up to eight people with 2 queen, 1 full bed, two twin beds, and is located within walking distance of Maddox Blvd., and Main Street for easy walking to the gift shops, restaurants, ice cream parlors, and much more. This home offers a spacious kitchen, large living room, and inviting sunroom that opens onto a shaded yard with patio and fire pit. Newly remodeled, comfortably furnished, and decorated with calming colors this is the perfect spot for some much needed rest and relaxation. We ask that you bring your own linens (2 Queen, 1 Full, 2 Twin), towels and washcloths. This home has a NO PETS and NO SMOKING policy. A washer/dryer is provided for your convenience. Please leave the home in a neat and tidy condition. We invite you to relax, unwind, and enjoy a memorable i

Located in Chincoteague Island, Virginia, United States. Shell Cottage - Pet friendly, Hot tub, Fenced yard! Come and enjoy a delightful vacation at "Shell Cottage"! Located on the popular East Side of Chincoteague Island, you'll enjoy water views of the Assateague Channel and lounging on the outside decks (one which includes an outside shower). This open floor plan home features two bedrooms downstairs (both with a queen bed and a TV each), a half bathroom, and spacious living room & kitchen. Upstairs you'll find 2 more bedrooms (one with twin trundle and the other with 2 twins) and a full bathroom. Just a short drive to the Memorial Waterfront Park, public boat launch, downtown area and restaurants! Shell Cottage also includes all the modern conveniences such as wireless internet, washer/dryer, dishwasher and more. And you'll have room to park your boat and trailer. This just may be your perfect vacation spot!- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!- No smoking is p

Located in Greenbackville, Virginia, United States. Breathe the Bay - Waterfront w/ Dock, Pool & Golf! Whether you are looking for a romantic getaway, family vacation, girls weekend, or just a quiet spot to enjoy the serenity of the Bay----This is the beach house for you!Breathe the Bay is located in a large, but quiet community filled with many amenities. The decor is coastal, clean and modern with simple lines and beautiful artwork. It is the perfect beach home for your family's summertime (or anytime!) beach vacation! This coastal gem is loaded with amenities to ensure a week of fun for everyone, including a game room with a Ping-Pong table, air hockey, and foosball. It's perfect for after-the-beach enjoyment! The beautifully furnished home features quartz kitchen countertops and nice stainless steel appliances. The open floor plan offers easy access to the spacious living room with fireplace for crisp mornings. There is a queen bedroom located on the first floor, with a large tiled bathroom. Upstairs you will find 3 more bedrooms,

Located in Chincoteague, Virginia, United States. starbright Cottage - Perfect Location and Pet Friendly! Reach for the Stars on your next Chincoteague Island Vacation…..Welcome to whimsical Starbright Cottage on beautiful Chincoteague Island! This adorable 4 Bedroom home is not only in an amazing mid-Island location, it welcomes your whole family - including your friendly Dog! Starbright Cottage has the allure of a bygone era, combined with the modern Amenities you want and need. Perched at the corner of Chicken City Road and Church Street, you’re in the perfect location for all of your Island adventures. Walk or ride your bike to Shops, Dining, and even the Beach. With a spacious lot and Fenced-in Yard, it's a wonderful place for both the human and the furry members of your family. And there's plenty of room to park your Boat and other Water Toys!As you enter Starbright Cottage, the first thing you notice is the large Screened Porch that lines the front of the home. You can already see yourself curled up with a good book, or maybe e

Located in Greenbackville, Virginia, United States. Unique round house on canal with water views near Chincoteague with elevator This newly renovated unique round home features a spacious open floor plan with spectacular water views from every room. The large kitchen is fully equipped with everything you’ll need, and the dining table seats 8 people. The large comfortable living room (which includes a sleeper sofa) features a 65 inch flat screen Roku TV and blu ray player. The master bedroom and double bedroom include 32 inch Roku TVs. Free WiFi is provided to connect your digital devices and for streaming (no cable TV). Both bathrooms feature large luxury showers with multiple shower heads. The 3 main bedrooms have French doors opening onto the porch and ceiling fans. The spacious screened porch offers plenty of seating and a dining table so it’s perfect for enjoying the cool breezes off of the bay and the beautiful view of the canal. In addition, this vacation home offers extras including board games and puzzles, 2 crab traps and a dee

Located in Chincoteague, Virginia, United States. STUNNING WATERFRONT VIEWS! Relax and unwind at one of the most beautiful waterfront townhomes overlooking the Chincoteague Channel. With the living room and master bedroom balconies overlooking the Chincoteague Channel, you will take in some of the most peaceful sights Chincoteague has to offer. Every room boast a relaxing water view, with the ability to view both the sunrise and sunset. When you stay here you will really say "life is better on the water."Please let us know if you would like to rent the boat slip when making the reservation this will be $100 added to the reservation.*BREAKING NEWS* SEA GATE ANNOUNCES WITH SPRING IN FULL BLUSH AND SUMMER JUST AROUND THE CORNER WE ARE EXCITED TO OFFER THE AVAILABLITY OF LEVEL 2 ELECTRIC CHARGING FOR ANY OF OUR GUESTS WISHING TO VISIT CHINCOTEAGUE BUT CONCERNED ABOUT WHERE THEY CAN CONVENIENTLY REGHARGE THEIR EV’S WHILE ON THE ISLAND AND IN PREPARATION OF RETURNING HOME. OUR CHARGE IS PRIVATELY LOCATED IN OUR 2 CAR GARAGE. THERE IS A

Located in Chincoteague, Virginia, United States. Crepe Myrtle Cottage - Nothing but Southern Charm and Hospitality. Give me the Sea and a little Cottage just to be…. The first time we saw ‘Crepe Myrtle Cottage’, we felt an inviting warmth pulling us in. Very difficult to describe, it’s the feeling of true Southern Charm, mixed with the appeal of modern amenities and chic decor. To us, it is the absolutely perfect combination of the quintessential Chincoteague Cottage and all that is shiny and new - at the same time.Crepe Myrtle Cottage is easily spotted as you drive down Church Street, in the very heart of our beautiful little island. In the front yard, a wise and wonderful Crepe Myrtle Tree welcomes you with its winding and unique branches. This circa 1930’s home has been completely renovated - you are in for quite a surprise.Upon entering, the cozy Front Porch lining the cottage is so alluring. Whether curling up with a good book, or sharing stories of the day’s adventures, you already know you’ll be spending lots of time here. You

Located in Chincoteague, Virginia, United States. Blue Bayou-Private Deep Water Dock, Waterfront w/Sunset Views Delightfully updated traditional Chincoteague home.Bright, cheerful, beachy decor.View of bay and sunsets. Private Pier & Boat Dock.Short walk to downtown restaurants and stores.All living spaces and bedrooms are on the first floor.Queen Waterview bedroom with a private full bath.Queen bedroom with private half bath.The third bedroom with pyramid bunk is adjacent to a full hallway bath.Comfortable deck off of the kitchen.

Located in Chincoteague, Virginia, United States. Sailor's Rest-Great In-Town Location! Beautifully renovated Chincoteague home.In-town location - close walk to restaurants and stores.The owner offers a 20% Discount to Military Families.Great indoor and outdoor living space.Fenced, landscaped yard, comfortable deck with gas grill and patio heater.Watch the world go by from the front screened porch.First floor half bath off the kitchen area.The second-floor configuration is:On Right - bedroom with 2 twins.On Left - bedroom with pyramid bunks and a twin.2nd on Left - bedroom with a queen bed.A large bathroom is at the end of the hallway.Third-floor master bedroom with king bed, private bath, and a large balcony.