94,639 properties available

Located in Chincoteague Island, Virginia, United States. Waterfront on Marsh Island! Welcome to Lover's Lane - Live by the Sea, Love by the Moon. This super charming 1 Bedroom/1 Bath Condo will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel, the Causeway, and the Chincoteague Channel. Perfect for a Romantic Getaway, you'll have all the makings of a fabulous Chincoteague Island Vacation Experience! Let us help you experience our Island Paradise by living like a Local.....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. 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. An adorable Efficiency Condo that has had many updates, you will expe

Located in Chincoteague Island, Virginia, United States. Painted Pony Cottage - Pet Friendly! Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Painted Pony Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern Amenities, there's no better home base for making Chincoteague Island Vacation Memories. As you pull up to this whimsical Cottage, the White Picket Fence and Sea Glass Blue Door are so welcoming. You can already feel yourself relaxing. Just the thought of sipping Sweet Tea on that Screened Porch - you can hardly wait. Located in the heart of Chincoteague Island on Willow Street, you are tucked away in a quiet location, yet close to everywhere you want to be. Walk to the Carnival Grounds in July to enjoy our famous Firemen's Carnival, and visit the ponies penned up just a short walk from the Cottage. There is ample parking for 3 Cars just behind the house, off

Located in Chincoteague Island, Virginia, United States. Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing O’Connor Properties is pleased to offer Jay’s Waterside Retreat. We provide a vacation experience designed for your convenience. Our vacation properties provide just about everything you need. Just bring food and clothing and let us take care of the rest. Here’s a sampling of what we include:2 Kayaks 4 bicycles Towels & LinensFully stocked kitchen including soaps & paper productsEV Charger: Level 2-Charging for both Tesla & Other EVsWe are committed to doing everything we can to make our rental properties a respite to escape, relax, and REJUVENATE.★ Jay's Waterfront Retreat is part of of the owner managed properties of O'Connor Properties. We have hosted hundreds of guests in Jay's over the last 4 years and have graciously received mostly five star reviews. * Perfect for a romantic getaway. Our waterside fire pit is the perfect place to unwind with your significant other. * Families love crabbing a

Located in Chincoteague Island, Virginia, United States. Ocean East 1 is a beautifully located Vacation Home and even welcomes your famil Ocean East 1 - Because not all who wander are lost....... Welcome to Ocean East 1 on the Eastside of Chincoteague Island. This lovely End-Unit Townhome has it all - a comfortable layout, sweeping Views of the Assateague Channel & Lighthouse, Water Access, and even welcomes your well-trained Family Dog! As you enter Ocean East 1, all eyes will be on your breathtaking Views - you can already feel yourself beginning to relax. This End-Unit Townhome has all you need to make incredible Chincoteague Island Vacation Memories. You will love the Open Floor Plan that invites everyone to spend time together and share stories of the day's Adventures. On the 1st Floor, you will find a spacious Living Area comfortably furnished and a wall of windows to the water. Relax in the Central AC while enjoying the Flat Screen Cable TV and Free WiFi after a fun-filled day on the Beach. You won't want to leave the huge Bayfront

Located in Greenbackville, Virginia, United States. Stunning waterfront panoramic view getaway house Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself in jaw-dropping panoramic canal views of the Chincoteague Bay. Secluded escape for the nature enthusiast, balanced with country club amenities. Pools, boating and a golf course are within walking distance. Outdoor adventures and pristine beaches are just a short drive away!This property was designed to gather, recharge, explore, love, work remotely and inspire.The house has recently undergone an extensive renovation and new elements are being added weekly. Full linen package included in your reservation, no additional fees! Lighting fast Starlink Internet!As you approach the property, prepare to be wowed by the view you will enjoy during your stay. Every room of the house has a waterview! The home is directly on the waterfront with a dock on a navigable canal to the Chincoteague Bay. Bring your boat or jetski a

Located in Chincoteague, Virginia, United States. Cattail Cottage -Single Family Home -Close to Town-Linens and Towels Provided Amenities: Central A/C, Cable TV, Microwave, WiFi, Deck, Charcoal Grill, Washer and DryerCharming Cottage located on a quiet private lane. A great " in town" location. Perfect for walking or biking to Main Street and Maddox Blvd. activities, shops and eateries. A short drive to the beach and marina areas. This home will pleasantly surprise you ! Offering a large deck, and grill and spacious sun room to relax and enjoy your visit. Linens and towels are provided with this house as well as beach chairs and an umbrella. 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). Bed Sizes: 1 King, 1 Queen Sleep Sofa, FutonSaturday Change Over$ 100 - 160 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 Greenbackville, Virginia, United States. Pier Pressure - Beautiful Canalfront in Captain's Cove! Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous Pier Pressure in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom Waterfront Dream Home has something for everyone in the family. Located at the water’s edge directly on the Chincoteague Bay, Pier Pressure is a Water Lover's delight, and 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. Have the best of everything, right in the heart of the Eastern Shore! This incredible home is a veritable Waterfront Playground - loaded with all the bells and whistles, boredom will be nonexistent! Relax on your Waterfront Deck and watch Herons and Egrets fish for their morning meal - or the kids, for that matter, as you

Located in Chincoteague, Virginia, United States. Find your 'Sea Treasure' on Chincoteague Island! Looking for an incredible Chincoteague Island Vacation Experience? You just found it at Sea Treasure - a beautiful Duplex that sleeps 6 more than comfortably in the very heart of our special Island. Located on Ridge Road, right next to famous Pony Swim Lane, you can relax on your Screened Porch and take in amazing Views of Assateague Island and our Famous Wild Ponies. You can even watch the Pony Swim without leaving your chair! Have a larger family or traveling with a group? Sea Mist, Sea Treasure's Sister Home, is right next door. These gorgeous Homes share amazing Views, but offer privacy, as well. Just a short stroll from Memorial Park, you're in the right location for all sorts of family fun!As you pull into the driveway, you can already catch a glimpse of the water - even when it's not Pony Swim, you can feel the excitement of this location and all it has to offer.  Sea Treasure has a wonderful Open Layout - spend time with those yo

Located in Greenbackville, Virginia, United States. Salty Paws - Dog Friendly and close to Chincoteague! Looking for a different kind of Beach Vacation? Dad likes to Golf, Mom and the kids want the Beach, and you don't want to leave Fido behind? How do you please everyone, you ask? We’ve got the answer right here at Salty Paws in beautiful 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 to Chincoteague and Assateague National Seashore, where our famous Wild Ponies roam free. This Brand New Custom home sits directly on the Golf Course, yet is only a few blocks away from the pristine Chincoteague Bay. Bring the Boat - you can fish or sandbar one day, and golf the next! Have a Pool day, or burn some Vacation calories in the Fitness Center (Fees Apply). And if you’re looking for some OC excitement, Ocean City, Maryland is a short 45 minute drive away, and Virginia Beach is only 2 hours. Have the very best of everything, right in the hear

Located in Chincoteague, Virginia, United States. ‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water! Escape to coastal paradise with this charming vacation rental in Chincoteague Island, VA. Spend your getaway with our Chincoteague Ponies — or bring your own! Offering a barn with stalls and a horse pasture with a run-in, this spacious 2-bedroom, 2-bath home is the perfect retreat for avid riders. Witness a sunset on the beach, explore Chincoteague National Wildlife Refuge and Assateague Island, or simply cozy up by the fireplace. Don't miss out on this gem for your visit to the Eastern Shore!-- THE PROPERTY --Horse-Friendly Property | Bedroom 1: King Bed | Bedroom 2: Queen Bed | Sunroom: Sleeper Sofa | Living Room: Sleeper Sofa INDOOR LIVING: Smart TV, board games, books, fireplace, group-friendly dining table, sunroomOUTDOOR LIVING: 2 12x12 horse stalls w/ pasture, front porch w/ outdoor seating, garage game room w/ ping pong table KITCHEN: Cooking basics, Keurig coffee maker, dishwasher, stove/oven, refrigerator, microwave, kettle, to

Located in Chincoteague Island, Virginia, United States. Sun Singer - 2BR townhome with Waterview community pier. Decks-Pet friendly! Amenities: Central A/C, 2 Smart TVs (bring your own login info for Prime, Netflix and Hulu), Bluetooth Speaker, WiFi, Microwave, Dishwasher, W/D, 2 Decks, Charcoal Grill, Shared Crabbing Pier, Open Outside Shower (hot and cold), Allows Dogs OnlyLovely Pet Friendly Townhouse located near the water. Enjoy the community pier or sit and relish in the beautiful views of the channel. This 2 bedroom, 2 and a half bath property provides everything you need for a pleasant and relaxing vacation. 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). Bed Sizes: 1 Queen and 1 Bunk w/ a Double and a TwinSunday Changeover$ 93-175 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. 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.