358,603 properties available

Located in Chincoteague, Virginia, United States. Waterfront Living at its finest on Chincoteague Island! There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the whole family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague Island to make Memories that you'll treasure forever. And Island Haven is the perfect place to make this happen - the Sun, the Sea, and Views that are simply unforgettable. This gorgeous Duplex sleeps 8 and is located on desirable Piney Island, the closest community to Assateague National Seashore. Ride your bike to the Beach, Dining, Activities, and more! You'll love returning to this tranquil Waterfront Community lined with whispering Pines, which even has its own Kayak Launch area. Sitting directly on the Assateague Channel, you have incredible Views of both the Channel and Assateague Island right from your two-levels of decking. With

Located in Chincoteague, Virginia, United States. Willet's Way-Waterfront w/ Private Dock, Closest Neighborhood to Beach Nestled in the pines, this secluded home affords outstanding views of Assateague IslandClose to Wildlife Refuge and entrance to beachThis unique home offers reverse floor plan with great privacy and wonderful viewsThe first level has 2 bedrooms, first with a queen and second with a kingFull bath with access from queen room and hallLarge Sunroom which has been converted into a semi-private bedroom with 3 twins.The second level Living Room has a wall of sliding doors which open to large waterfront Sunroom & Deck.Kitchen, full bathroom and laundry are also on upper level.Dock your boat or crab and fish from Private Pier.Community kayak and canoe launch is just down the street.

Located in Chincoteague Island, Virginia, United States. Enjoy sandpiperHouse on Chincoteague's Peaceful Piney Island! A virtual office Fall pony roundup October 2024 FULL WEEKS ONLY DURING JUNE, JULY and AUGUSTGreat fall weekends !Stay in Chincoteague and swim, hike, bike, kite, birdwatch, etc. in Assateague. Our home is conveniently located on Chincoteague’s Piney Island, designated bird sanctuary and gateway to Assateague Island National Seashore. Whether you bike to the beach every day, or hang out at home on the deck, you can enjoy nature immersion at it's best! This modern style house has new gorgeous hardwood floors in an open floor plan living-dining area, fresh paint, new fans, remodeled master bath and bedroom, new gas range , dishwasher and many other updates .Our home has three bedrooms. The bedrooms were remodeled this year with a new queen bed, mattress, floors, lamps, paint etc. and the master bath was remodeled last year. Master bedroom also has a flat screen TV. Our second bedroom has a NEW queen bed. Our third bedroom,

Located in Chincoteague, Virginia, United States. Avocet-Close to Beach, Shared Community Water Access, Limited Water View Spacious home on Piney Island Close to the entrance of Assateague.Private Master Suite features:Sitting room with TV and sleeper sofa,bedroom with king bed, trundle with 2 twins,private bath and private access to the deck.Living room with TV and seasonal fireplace.Second Bedroom with a queen and master bath.Third Bedroom with two twins and adjoining hallway full bath.Enjoy a glimpse of the Assateague Channel from the Large sunroom.Avocet features an outbuilding with a ping pong table.Community kayak and canoe launch is just down the street.

Located in Chincoteague, Virginia, United States. The Tree House-Close to Beach Beautiful Views! The “Tree House and Casita” have been completely renovated from top to bottom!(New pictures will be posted after the renovations are completed)Fantastic location on Piney Island – you cannot get closer to the beach!This 4-season house – the tallest on Chincoteague Island – boasts sleeping for 15 people aswell as several communal spaces, including three heated, screened-in porches, four decks --the top two offering panoramic views of Assateague Channel and the iconic lighthouse -- andtwo indoor family rooms. The adjacent lot includes a basketball court, a smokeless firepit andample room for outdoor games. Here also sits the 800-square foot “Casita,” with its own fullbath, television area, as well as pool, ping pong and foosball tables!First Floor Features:The mudroom where you can leave your towels, sandy shoes and call the elevator, whichprovides access up to the fourth level, great for taking up groceries, luggage, and people!The second-f

Located in Chincoteague Island, Virginia, United States. Only 5 min to Assateague National Seashore! Newly Renovated and GORGEOUS for 2023!Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will? If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. Our Studio Suites have a Private Bedroom with queen size bed, and a separate living room with queen sleeper sofa. There is also a spacious Full Bath, and a Kitchenette fully equipped with cookware and dishes, 2 burner stove top, mini refrigerator AND a full size refrigerator, coffee maker, toaster and eating area. Our Studio Suites accommodate up to 4 guests. R

Located in Chincoteague, Virginia, United States. Quaint Cottages Near Everything on Beach Road Sand Dollar Cottage sleeps up to 6 with 2 queen size beds and a pull out couch. There are 2 bedrooms with a patio and a full size kitchen. There is 40 inch smart Flat Screen TV in the living room. At the entrance there is small room with a couple beach chairs. Our property is located by the mini golf courses, food trucks, and a bike and scooter rental place nearby. There is also a garden located on the property and plenty of parking. We look forward to hosting you at our cottage.

Located in Chincoteague, Virginia, United States. Waterfowl Watch Quiet area, Bikes included, family friendly, 5 ⭐️⭐️⭐️⭐️⭐️ local host Small family-friendly two bedroom cottage on Chincoteague Island! In a quiet residential area with a slight view of Little Oyster Bay across the street. One mile to Maddox Blvd, and three miles onto Assateague Island. Simple cottage features one queen, bunk beds with trundle and sleeper sofa. Located in quiet residential area, property is cute & clean, it is a beach cottage not a luxury resort. The view and experience are great and will be enjoyed by couples & families alike! So much to do on Chincoteague from getting back to nature or cruising the island in a golf cart and enjoying many shops and activities. Amenities include very large outside shower, fire pit, outdoor seating, charcoal grill, bikes (waiver required), backyard games and more. Military, first responder/law enforcement, nursing discounts! Premier host with another local property on the Chesapeake Bay! Please reach out with

Located in Chincoteague, Virginia, United States. Shallow Waters Villa THE REEF VACATION VILLAS INCLUDE THE FOLLOWING FOR OUR GUESTS:*All units sleep 6*Daily and Weekly Rentals Available*Full Kitchen *Use of Inclusive Indoor Pool*Free Wifi*4 FREE Maui Jack Waterpark passes (Seasonal)*Free Bike Rentals*On-Site Grills and picnic area*Free ParkingWe are located just a little over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the infamous wild ponies & the Lighthouse. This 2 Bedroom, 1.5 Bath Villa sleeps 6 and features a full kitchen with pots, pans, utensils, dishes and drinkware, toaster, coffee pot, microwave, refrigerator/freezer and oven. To make your trip to paradise even easier, we've included bed and bath linens, toilet paper, paper towels, trash bags and dish soap. Your Villa provides 2 parking spaces.Complimentary washers & dryers are located on property. Heated indoor pool is open April thru November.Close to the Beach...... Close to PERFECT!

Located in Chincoteague, Virginia, United States. Island Generations - Water Access, Boat Docking Traditional Chincoteague Island home charmingly updatedNewly bulkheaded boat dock on Little Oyster BayTwo bedrooms, each with queen bed and shared hall bathThe enclosed porch opens onto the large grassy yardFrom yard access lane to a private boat dock

Located in Chincoteague Island, Virginia, United States. Only 5 min to Assateague National Seashore! HUGE UPDATES for 2023 - it's gorgeous!Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will? If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. Our Studio Suites have a Private Bedroom with queen size bed, and a separate living room with queen sleeper sofa. There is also a spacious Full Bath, and a Kitchenette fully equipped with cookware and dishes, 2 burner stove top, mini refrigerator, coffee maker, toaster and eating area. Our Studio Suites accommodate up to five guests. Relax in the AC and enjoy F

Located in Chincoteague Island, Virginia, United States. Assateague Inn 107 on Chincoteague! Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will? If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. Assateague Inn 107A is the ONLY Apartment at The Assateague Inn. It features a Full Living Room with Sleeper Sofa, Flat Screen Cable TV, and Free WiFi. There is also a Full Kitchen with everything you need to make mealtime a bay breeze! Dine indoors in the AC, or Al Fresco at the Inn's shared Picnic Area with Grills and Picnic Tables. With a Private Bedroom with a comfy Queen Bed and the Sleeper Sofa, the

Located in Chincoteague Island, Virginia, United States. Crabby Pines - Pet friendly modern accommodations! Discover comfortable vacation living in this charming one-level ranch home. "Crabby Pines" offers a cozy retreat with three bedrooms and two bathrooms, providing ample room for relaxation and privacy. The house is ideally situated in a serene residential neighborhood and features modern amenities that ensure a seamless, convenient lifestyle.Enjoy the convenience of being just minutes away from the public boat ramp at Fur Landing. Outdoor enthusiasts will appreciate the close proximity to nature trails and a dog park, perfect for morning jogs or leisurely evening walks with your furry friends. Oh, did we mention this home is pet friendly? Additionally, the property is located near the 'Beach Road,' a vibrant area bustling with mini-golf, dining options, ice cream shops, and boutiques - offering endless entertainment options.This welcoming home is designed with practicality in mind, ensuring that each space is utilized efficiently while

Located in Chincoteague Island, Virginia, United States. Down the street from the Beach! Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will? If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. Our Studio Suites have a Private Bedroom with queen size bed, and a separate living room with queen sleeper sofa. There is also a spacious Full Bath, and a Kitchenette fully equipped with cookware and dishes, 2 burner stove top, mini refrigerator, coffee maker, toaster and eating area. And 209S has TWO mini-fridges! Our Studio Suites accommodate up to 4 guests. Relax in the AC and enjoy Flat Screen Cable TV an

Located in Chincoteague, Virginia, United States. Shipwreck Villa THE REEF VACATION VILLAS INCLUDE THE FOLLOWING FOR OUR GUESTS:*All units sleep 6*Daily and Weekly Rentals Available*Full Kitchen *Use of Inclusive Indoor Pool*Free Wifi*4 FREE Maui Jack Waterpark passes (Seasonal)*Free Bike Rentals*On-Site Grills and picnic area*Free ParkingWe are located just a little over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the infamous wild ponies & the Lighthouse. This 2 Bedroom, 1.5 Bath Villa sleeps 6 and features a full kitchen with pots, pans, utensils, dishes and drinkware, toaster, coffee pot, microwave, refrigerator/freezer and oven. To make your trip to paradise even easier, we've included bed and bath linens, toilet paper, paper towels, trash bags and dish soap. Your Villa provides 2 parking spaces.Complimentary washers & dryers are located on property. Heated indoor pool is open April thru November.Close to the Beach...... Close to PERFECT!

Located in Chincoteague Island, Virginia, United States. A Beach Bargain in Chincoteague! Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will? If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. Our Studio Suites have a Private Bedroom with queen size bed, and a separate living room with queen sleeper sofa. There is also a spacious Full Bath, and a Kitchenette fully equipped with cookware and dishes, 2 burner stove top, mini refrigerator, coffee maker, toaster and eating area. Our Studio Suites accommodate up to five guests. Relax in the AC and enjoy Flat Screen Cable TV and Free WiFi after a fun-fil

Located in Chincoteague Island, Virginia, United States. Find your peace at One Peace Cottage Peace. Love. Beach.Have you been yearning for a break from the hectic day to day? An affordable getaway that will bring those together who matter most - and without breaking the bank? We’ve got you covered - take a look at One Peace Cottage on beautiful Chincoteague Island - where our Wild Ponies roam free, and there’s not a high-rise building to be found. Just natural beauty and a peaceful paradise…..A visit to One Peace Cottage is like coming home to visit an old friend. Modest, yet so charming, this one-level home sits on Deep Hole Road, in the very heart of Chincoteague Island. You’re just 5 minutes from Assateague National Seashore, and a hop, skip, and jump from Restaurants, Shops, and Entertainment. You’ll love relaxing in the cozy Living Area and enjoying Free WiFi and Flat Screen Cable TV with Streaming. It’s perfect for kicking back after a day of fun in the sun at the Beach, and sharing stories of the day’s adventures. If you’re more of a

Located in Chincoteague Island, Virginia, United States. Island Sage on Chincoteague Island! Welcome to Island Sage on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This cozy Vacation Home is just that - a HOME, not just a place to lay your head at night. Located in popular Piney Island, which happens to be the closest community to Assateague National Seashore, you will love Island Sage's quiet and peaceful location on a cul-de-sac, yet still close to everywhere you long to be. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our country are just a short stroll or bike ride away! Did you know that Assaeague National Seashore is the most visited National Park in our country? Spend a little time here and you will discover why this is.....Surrounded by Magnolia Trees, this lovely home truly makes you feel at one with nature. You'll love relaxing on the huge Screened Porch - a great place to enjoy some Fresh Local Crabs or the Fresh Catch of the Day, which wit

Located in Chincoteague Island, Virginia, United States. Southern Dream - Water views; Screened porch! Charming 3 bedroom ranch home located in one of Chincoteague Island's residential communities. Nice, quiet location with a water view of Oyster Bay. You'll enjoy the easy, one-story floor plan with open living room/kitchen/dining areas. If you love the outdoors, spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high speed internet, charcoal grill and an outside shower will ensure your comfort during your stay! ​​​​​​​- 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 as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Located in Chincoteague Island, Virginia, United States. A Bargain on Chincoteague Island! Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will? If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. Our Studio Suites have a Private Bedroom with queen size bed, and a separate living room with 2 twin sleepers. There is also a spacious Full Bath, and a Kitchenette fully equipped with cookware and dishes, 2 burner stove top, mini refrigerator, coffee maker, toaster and eating area. Our Studio Suites accommodate up to five guests. Relax in the AC and enjoy Flat Screen Cable TV and Free WiFi after a fun-fille

Located in Chincoteague, Virginia, United States. Palm Villa THE REEF VACATION VILLAS INCLUDE THE FOLLOWING FOR OUR GUESTS:*All units sleep 6*Pet-Friendly Unit*Daily and Weekly Rentals Available*Full Kitchen *Use of Inclusive Indoor Pool*Free Wifi*4 FREE Maui Jack Waterpark passes (Seasonal)*Free Bike Rentals*On-Site Grills and picnic area*Free ParkingWe are located just a little over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the infamous wild ponies & the Lighthouse. This 2 Bedroom, 1.5 Bath Villa sleeps 6 and features a full kitchen with pots, pans, utensils, dishes and drinkware, toaster, coffee pot, microwave, refrigerator/freezer and oven. To make your trip to paradise even easier, we've included bed and bath linens, toilet paper, paper towels, trash bags and dish soap. Your Villa provides 2 parking spaces.Complimentary washers & dryers are located on property. Heated indoor pool is open April thru November.Close to the Beach...... Close to PERFECT!

Located in Chincoteague Island, Virginia, United States. Tranquility - Brand new home in quiet location! Welcome to Tranquility! This show stopper of a home is a brand new construction, featuring 2 bedrooms, 2 bonus rooms and 2.5 baths. Sleeps up to 11 with 1 king, 2 queens, 2 queen conversion sofa/sleepers and a twin fold-out sleep chair. Deep Hole Hideaway rental properties can accommodate up to 23 people by renting all 3 units in this complex! (based upon availability) Tranquility Great for family reunions or large gatherings! Please reach out to our office or check out "Escape at Deep Hole " and "Serenity at Deep Hole" for multi home bookings. Pet friendly, private and quiet. This property allows for entertainment and relaxation for both you and your kids! There is also outdoor seating, cornhole, a firepit, picnic tables and barbecues for additional recreation for your vacation. Book your stay today, this one won't last long! - Linens and towels are not included with your reservation. Please inquire about our new attractive linen packag

Located in Chincoteague, Virginia, United States. Chincoteague Island Home- "Blue Tide Townhome" Bikes/Kayaks Included! We welcome you and your family to “seas the day” at our unique island vacation home. Our quiet yet central location is just a half mile from Chincoteague’s main drag, Maddox Blvd! Enjoy your saltwater escape with our kayaks, bikes and boogie boards by day, and sit around our fire pit by night. Our family fell in love with this slice of paradise many years ago, and we want to give your family the opportunity to experience all of its beauty with the best stay possible.~ABOUT THE HOUSE~This is a 4 bedroom, 2.5 bathroom, 1636 sq. ft. townhome located in Deep Hole, Chincoteague. We have a full kitchen, living room, dining area, small office space, and fire pit. This home is perfect for a large family or two small families. We comfortably sleep 12 but can sleep a maximum of 15 with use of our sofa bed and trundle bed. Our kayaks, bikes, beach supplies, and grill are available for NO additional fee. Please note, LINENS AND

Located in Chincoteague, Virginia, United States. Fishhook Hideaway - Adorable AND Affordable! Sometimes you just have to go with the waves….. Looking to catch a beach getaway at a family-friendly price? Then look no further than Fishhook Hideaway on Deep Hole Road - truly the catch-of-the-day! This adorable 2 Bedroom/2 Full Bath home is located in the heart of our little Island - just a short stroll from Maddox Boulevard, Steamers, and The Island Creamery, and a very short 5 minute ride to Assateague National Seashore!Fishhook Hideaway has all you need for the perfect family getaway. You’ll love relaxing in the comfort of Central AC after a fun-filled day at the Beach, and enjoying Free WiFi and Flat Screen TV. Newly renovated and with brand new furnishings, it’s comfy and cozy. Just off the Living Area, you’ll find a Full Bath with Tub/Shower Combo, and a Full Size Washer and Dryer for your convenience. Wander up just 3 steps, and you’ll find the Well-stocked Kitchen supplied with all you need to make mealtime a bay breeze. No need