Vacation Home Rentals By Owner In Chincoteague, VA

Amenities:3BR/2B***(2B down/2BR 2nd floor/1BR 3rd floor) Waterfront with shared dock. Central A/C, Microwave, Dishwasher, W/D, TV, VCR, DVD, WIFI, Cable, Gas Grill, Enclosed Porch, Outside Shower. WIFI. Pet FriendlybrbrSit 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. Newly painted, Large kitchen with stainless steel 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. Dining room with large table will seat 8 and spacious living room, there is plenty of space to spread out. Waterfront with shared dock. PET FRIENDLY. $ 75 per pet non-refundable fee. brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrBed Sizes: 1 king, 1 Queen, 1 Double, 1 Twin Sleep Sofa, QSSbrbrSunday Change Overbrbr2026 Prime Season Rate $ 1701 per weekbr2026 Off Season Rate $ 1550 per week / $ 222 per night with 3-night minimumbrNew for 2025 Welcoming Pets brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Bunting House - Waterfront w/ Shared Dock - Close to town . Pet friendly.

Chincoteague, Virginia, United States

Bed

Bath

8

Sleeps

$238.55

Freshly updated townhouse with access to a shared pier on the creek, perfect for crabbing. Conveniently located near shops, restaurants, and activities, with easy access to Assateague Island just a short drive away.brbrThe first floor features a beautifully updated kitchen, laundry, half bath, and living room that opens to a covered deck. Upstairs, one bedroom has a queen bed with a twin trundle, full bath, and a waterview balcony. The second bedroom also includes a queen bed with twin trundle, full bath, and access to a private balcony. Large grassy areas provide plenty of space for children to play.

Ride the Wave - 2BR | Close to Maddox | Shared Pier

Chincoteague, Virginia, United States

Bed

Bath

6

Sleeps

$509.93

Enjoy Chincoteague Island waterfront living at this inviting canal-front home in the quiet community of Richardson’s Landing. With a private boat dock on the canal leading directly to Oyster Bay, this home is perfect for boating, crabbing, fishing, and taking in the peaceful coastal scenery.brbrRelax on the spacious screened porch or outdoor deck, where you can enjoy beautiful water views, coastal breezes, and time with family and friends. Whether you’re sipping morning coffee or winding down after a day on the water, the outdoor spaces make this home a true retreat.brbrThe SpacebrbrOpen Living AreabrInside, the home features a bright and comfortable open floor plan, ideal for gathering, dining, and relaxing together. The layout is designed for both comfort and convenience, making it perfect for families or groups.brbrFirst Floor Bedrooms and BathsbrbrPrimary bedroom with queen bed, private bathroom, and direct access to the screened porchbrbrTwo additional bedrooms, each with a queen bedbrbrFull hallway bathroom shared by the additional bedroomsbrbrSecond Floor Loft and Bonus SpacebrbrLoft area with two pyramid bunk beds, perfect for kids or extra guestsbrbrCozy sitting area with TV and table for games, crafts, or relaxingbrbrGreat flexible space for families or a kids’ hangout zonebrbrOutdoor and Waterfront AmenitiesbrbrPrivate canal-front dock with direct access to Oyster BaybrbrScreened porch with water viewsbrbrOutdoor deck for relaxing and diningbrbrIdeal location for boating, crabbing, kayaking, and fishingbrbrQuiet neighborhood setting in Richardson’s LandingbrbrPrime Chincoteague LocationbrbrLocated just a short drive from downtown Chincoteague, you’ll have easy access to local restaurants, shops, the movie theater, and the waterfront park. A quick trip takes you to Assateague Island for beaches, wildlife, and the famous wild ponies.brbrWhy Guests Love This HomebrbrCanal-front location with private dock and bay accessbrbrSpacious screened porch and deck with water viewsbrbrFamily-friendly layout with loft and bunk spacebrbrQuiet community close to town and attractionsbrbrPerfect for boating, crabbing, and relaxing coastal vacationsbrbrYour Chincoteague Waterfront EscapebrbrWhether you're out on the water, relaxing on the porch, or enjoying family time in the loft, this canal-front Chincoteague home offers everything you need for a memorable and relaxing getaway.

Island Girl | 4BR Canal-Front Home w/ Private Dock & Screened Porch

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$257.17

Surf and Wind is ideally situated along a 5K bike and walking path, with nature loops nearby for scenic strolls. This charming cottage is within walking distance of shops, restaurants, ice cream, and many local attractions, while still enjoying the quieter, low-traffic location of Deep Hole Road.brbrThe spacious and comfortable screened porch is perfect for relaxing, and the fenced side yard features a fire pit and gas grill for outdoor enjoyment.brbrOn the first floor, you’ll find a fully enclosed sunroom with a twin trundle (2 twins), heat and A/C, and a half bath. The kitchen includes an eat-in dining area and opens to the living room. There is also a first-floor bedroom with a full bed and a shared full bath in the hallway.brbrThe second floor features a bedroom with a king bed, providing a peaceful retreat with ample privacy.brbrThis home blends convenient access to town with a tranquil setting and comfortable living spaces.

Surf & Wind- Fire Pit, Fenced in Yard

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$245.01

Amenities: 3BR / 2BA *** ( Single Level Home) ( 1Q,2D) Amenities: Central A/C, Microwave, W/D, DW. WIFI. Gas Grill, Screened Porch, Front Deck, short distance from the beach. Keurig and Regular Perk Coffee Pot. 4 Bikes and beach chairs are provided.brbrTucked away in Piney Island, just a few minutes from Assateague beach, this Outstanding beach home set up perfect for your whole family to relax and enjoy your beach vacation. The ground level has a large, screened area with full bathroom, the living and sleeping area is all on one floor with 3 bedrooms, 1 bathrooms. Linens and Towels Provided. 3 Kayaks and Vest provided and 4 bikes available. No smoking or vaping. No Pets. brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less, then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge, and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brBed Sizes: 3 Doubles brbrChange Over Saturday brbr2026 Rate Prime Season: $ 1500 per week br2026 Pony Swim Week $ 1701 per week br2026 Rate Off Season: $ $ 1204 per week / $ 172 per night ( 3 night minimum)brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Ohana Sunrise - VERY NICE 3BR, Close to the beach - Linens & Towels provided

Chincoteague, Virginia, United States

3

Bed

Bath

6

Sleeps

$369.16

Great canal-front home in the quiet community of Richardson's Landing. Dock your boat or go crabbing along the private bulkheaded shoreline, and enjoy kayaking in the canal that leads out to beautiful Oyster Bay.brbrA large screened porch provides the perfect space for gathering with everyone, and the canalside firepit with seating is ideal for outdoor evenings.brbrThis one-story home features three bedrooms, a private fourth sleeping area, and three full bathrooms. The spacious living room, fully equipped kitchen, and dining area make it perfect for family vacations.brbrThe main king bedroom has a private bathroom. The second bedroom has a queen bed, and the third bedroom has a full bed. A second full bath is located in the hallway and has been fully updated. A sunroom with a queen sleeper sofa provides a fourth private sleeping area. The laundry room and third bathroom are conveniently located off the kitchen.brbrTwo kayaks and cornhole boards are provided for outdoor fun.

Meme’s Landing-4BR Canal Front | Fire Pit | Kayaks

Chincoteague, Virginia, United States

4

Bed

Bath

8

Sleeps

$193.2

Amenities: 3BR/2B ( 2 downstairs / 1 upstairs) ( Bed Sizes: 2Q, 2T) Newly remodeled for 2025. Central A/C, Microwave, Dishwasher, W/D, WiFi,Deck, FirepitbrbrNewly remodeled for 2025 Season. Bright and spacious duplex located on private lane. In walking distance of many island attractions. 2 bedrooms downstairs, one bedroom upstairs. Have a large group check availability of Ocean Hous1 the other side of the duplex. brbrTHIS HOME DOES NOT PROVIDE LINENS OR TOWELS. PLEASE BRING YOUR OWN OR CALL US TO RENT THEM. 3BR/2B ( 2 downstairs / 1 upstairs) ( Bed Sizes: 2Q, 2T)brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less, then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge, and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrNo LinensbrbrBed Sizes: 2Q, 2TbrbrSunday Change Overbrbr2026 Prime Season Rate $ 1120 per week/ $ 160 per night ( 3 night minimum) br2026 Off Season Rate $ 924 per week / $ 132 per night ( 3 night minimum) brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Ocean House 2 - duplex -Newly renovated. 3BR, 2 Bath duplex with back deck.

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$284.29

Seaside Rendezvous on Chincoteague Island brWelcome to our 3 Bedroom 2.5 Bath townhome in beautiful, secluded, Silver Sails Landing. So much to love here. Comfy and spacious rooms and so much to do! Crabbing, fishing, biking, swimming (in season)exploring and relaxing are just a few offerings at SRCI!brWe can't wait to welcome you into our home, which is equipped with a fully stocked kitchen! There is also a coffee bar, games and broadband with streaming via Roku! Total relaxation is just a click away!

Seaside Rendezvous Chincoteague, Seaside Rendezvous Chincoteague

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$522.0

Black Skimmer - The Best Days are Beach Days..... br br Black Skimmers are known for their unique grace as they forage in flight - the same can be said for this one-of-a-kind Vacation Home on Chincoteague Island. There's nothing quite like this beautiful Home that combines the Modern Amenities you want and need, with Historic Touches of yesteryear that only a Home born in the 1940's can offer. Located in the heart of the Island on Ridge Road and just a short stroll to Memorial Park, you're close to everywhere you want to be, but will feel like you're a million miles away from the real world. And since it's Pet-Friendly, you really can take the whole family on an incredible Vacation! Kick off your flip flops and get ready for a Vacation Experience your family will forever treasure......br br Black Skimmer is a bit more like a Compound - the grounds feature a Main House with 3 Bedrooms, a Guest House that sleeps 2, a Private Pool with expansive Deck , Game Room, and so much more. You may leave each day to explore our charming Island or visit the Wild Ponies on Assateague, but you will eagerly return to the family fun this incredible Home offers. br br The Main House has Historic Touches that we simply adore. You'll love relaxing in the spacious Living Area with gorgeous Coastal Decor, Refurbished Hardwood Floors, and Arched Doorways, while enjoying Free Wifi and Flat Screen Cable TV. What a great place to share stories of the day's Adventures - or curl up with a good book in the cozy Sitting Area. The wonderful layout of Black Skimmer allows comfortable Family Time without ever feeling crowded, and the phrase I'm bored will never be heard with so much to do at this awesome Home. br br The Chef in your Family will love the well-stocked Kitchen with everything you need to make mealtime super easy. Sea Grass Green Walls & Beachy Bead Board are a great backdrop for the Custom Back Splash made from stone & sea glass. Dine together in the spacious Dining Room, or grab a quick bite before hitting the Beach in the Breakfast Nook. Even better, grill the Fresh Catch of the Day and dine Poolside - so many options!br br In the Main House are 3 spacious Bedrooms and 2 Full Baths. Downstairs Bedrooms 1 features Sunny Yellow Walls and a comfy Queen Bed. Down the hall, Bedroom 2 is great for the kids with 2 Twins. A beachy blue Full Bath with Tub/Shower Combo and Hardwood Floors is convenient to both Bedrooms and the Living Area. Wandering up the very cool winding stairs, you'll find a Play Room the kids will just love with some toys for their enjoyment. Also upstairs is a Master Bedroom that will take your breath away. With soaring ceilings and tons of windows, the Master feels like a Vacation in its own right. Wake up in the comfy King Bed to take in lovely Water Views & Views of Assateague Island. There is also a Daybed with Twin Trundle, and a Full Bath with Walk-in Shower. br br Wandering outside to the Guest House that sleeps 2, you'll find a Queen Bed and many comforts of Home including Flat Screen Cable TV, a Mini Fridge, Coffee Pot, Full Bath, and more, all gorgeously decorated with a distressed Coastal Flair. Above the Guest House is the Game Room - tons of family fun will be had here with both a Pool Table and a Foosball Table. Enjoy lovely Views from the furnished Upper Deck, or lounge by the Pool while the kids have a blast. Maybe even sneak away for a nap in the shaded Hammock - when is the last time you actually took a nap ! br br And there you have it - the absolute perfect Family Vacation that even your furbaby will adore. Homes like Black Skimmer don't come along every day, so don't wait - let's plan some Island Time today!br br Black Skimmer - The tans may brush off, the salt may wash away, but those Memories will last forever......br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with $100 Pet Fee. Dogs MUST be current on Flea/Tick Preventative & Immunizations. No Cats. LINENS INCLUDED, NO SMOKING, NO VAPING. FAMILIES ONLY AND MUST BE AT LEAST 25.

Black Skimmer by Seaside Vacations & Sales

Chincoteague, Virginia, United States

4

Bed

3

Bath

10

Sleeps

$317.13

Just over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the infamous wild ponies & the Lighthouse, this flowing 3 BEDROOM / 3 BATHROOM house is next to the heated indoor pool and accommodates up to 10 guests. brThe full kitchen features all basic pots, pans, utensils, dishes, drinkware and toaster, as well as a coffee pot, microwave, refrigerator/freezer and oven. We've included all bed and bath linens, 4 rolls of toilet paper, a roll of paper towels, 5 trash bags and dish liquid to make your travel to paradise easier! An in unit full size washer and dryer round out this perfect vacation home. Both a full ramp and steps allow easy access into the home and 2 parking spaces are provided. brBedroom 1 One Queen Bed * Bedroom 2 has One Queen Bed *Bedroom 3 has One Queen BedbrbrThe very spacious living room offers two sets of twin with trundle beds, as well, for additional sleeping in a tucked away nook.brbrbrbrTHE BEACH HOUSE INCLUDES THE FOLLOWING FOR OUR GUESTS:br*The Beach House sleeps 10br*Daily and Weekly Rentals Availablebr*Full Kitchen br*Use of Inclusive Indoor Poolbr*Free Wifibr*4 FREE Maui Jack Waterpark passes (Seasonal)br*Free Bike Rentalsbr*On-Site Grills and picnic areabr*Free ParkingbrWe 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.brbrComplimentary washers & dryers are located on property. Heated indoor pool is open April thru November.brClose to the Beach...... Close to PERFECT!

Beach House

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$309.71

Just a little over a 1/2 mile to Assateague Island National Park, Chincoteague Wildlife Refuge, the famous wild ponies & the Lighthousebr2 BEDROOM / 2 BATH house easily accommodates up to 9 guests. The full kitchen offers basic pots, pans, utensils, dishes and drinkware, as well as a toaster, coffee pot, microwave, refrigerator/freezer and oven. Your bed and bath linens are included, as well as a welcome kit of toilet paper, paper towels, trash bags and dish detergent. An in-unit washer and dryer rounds out this complete vacation rental. Both a full ramp and steps allow easy entry into the house. This is the second house from the pool and is provided with 2 parking spaces. br Bedroom 1 has TWO full size beds Bedroom 2 has ONE queen Bed and ONE twin bedbrbrThe nicely sized living room offers one twin with trundle bed for additional sleeping. brbrTHE HARBOR HOUSE INCLUDES THE FOLLOWING FOR OUR GUESTS:br*Sleeps 9br*Daily and Weekly Rentals Availablebr*Full Kitchen br*Use of Inclusive Indoor Poolbr*Free Wifibr*4 FREE Maui Jack Waterpark passes (Seasonal)br*Free Bike Rentalsbr*On-Site Grills and picnic areabr*Free ParkingbrComplimentary washers & dryers are located on property. Heated indoor pool is open May through November.brbrClose to the Beach...... Close to PERFECT!

Harbor House

Chincoteague, Virginia, United States

Bed

Bath

9

Sleeps

$830.38

Delight the entire group with this superbly appointed and spacious waterfront home.brCanoe, fish, or crab right from the private dock—or simply relax and soak in the peaceful surroundings.brExpansive waterview decks provide the perfect spot to enjoy stunning sunrises over Little Oyster Bay.brbrFirst FloorbrThe first floor offers plenty of comfortable living space along with multiple sleeping options. One bedroom features a queen bed and a private bath with a shower stall. The second bedroom includes a queen bed and a twin, while the third bedroom offers three twin beds. A full hallway bath serves these rooms. A cozy sunroom off the kitchen includes a full-size sleeper sofa, making it perfect for teenagers or extra guests.brbrSecond FloorbrThe second floor features a beautiful waterfront queen bedroom with a luxurious private bath, complete with a jetted tub, large shower stall, and access to a private balcony overlooking the bay. A spacious loft provides additional lounge space with seating, a TV, and a cozy nook with a twin bed.

Brittany-Private Deep Water Pier & Boat Dock

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$258.98

New Rental for 2025. Amenities:3BR/2B***(1B Down2T , 2 bedroom (2Q) up) {2T,2Q} Linens and Towels Provided, screen porch, wifi, ROKU TV - 2 TV's, Washer/ Dryer and Outside Shower. NO SMOKING and NO PETS.brbrNew Rental for 2025. Immaculate 3 Bedroom, 2 bath home with lovely, landscaped back yard and patio area. Lg front screened in porch. Linens provided.brCentral air, gas grill, outside shower, washer / dryer fully equipped kitchen with microwave and dishwasher. This home is not recommended for small children because the yard is landscaped with cut stone. Very comfortable and spacious home located close to shopping and restaurants. No smoking, no pets allowed. Ring camera on front and back of this home. ** This property requires both Security Deposit and Damage Protection Plan. New for 2025 rentals.brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrBed Sizes: 2T,2Qbrbr2026 Prime Season Rate : $ 1603 per week / $ $ 229 per night ( 3 night minimum)br2026 Off Season Rate: $ 1225 per week / $ 175 per night ( 3 night minimum)brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ***

Cantering Sands- New for 2025 3BR/2Bath home w/patio & Sc Porch.

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$224.03

You’ll return again and again to this immaculate summer home.brEnjoy a large rear deck overlooking a fenced-in, private backyard—perfect for relaxing or entertaining.brbrThe first floor features a bright living room, a comfortable dining area, a well-appointed kitchen, and a convenient half bath.brUpstairs, you’ll find both bedrooms. The main queen bedroom includes its own private bath and a charming screened-in balcony, while the second bedroom offers two twin beds with an adjacent hallway bath.brbrIdeally located near Memorial Park and Historic Downtown, this home offers comfort, convenience, and the perfect coastal getaway.

Bridge Townhouse-Large Deck with Fenced in Yard. Close to Everything

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$322.66

Delightfully updated traditional Chincoteague home with bright, cheerful, beach-inspired decor. Enjoy beautiful bay views and unforgettable sunsets from your own private pier and boat dock. Located just a short distance from downtown restaurants and shops, this home offers both convenience and coastal tranquility.brbrAll living spaces and bedrooms are conveniently located on the first floor. The King water view bedroom features a private full bath, while the Queen bedroom includes its own private half bath. A third bedroom with a pyramid bunk sits adjacent to a full hall bath - perfect for families or groups.brbrRelax on the comfortable deck just off the kitchen or unwind in the charming pocket yard complete with a firepit - ideal for evening gatherings after a day on the water.

Blue Bayou- Sunset Views with Fire Pit, Private Pier & Dock.

Chincoteague, Virginia, United States

3

Bed

Bath

6

Sleeps

$407.63

Welcome to Baywatch, a stunning waterfront retreat on Oyster Bay in Chincoteague Island, Virginia, where breathtaking views, spacious living, and private amenities come together for the ultimate coastal getaway. This beautifully designed 4-bedroom home with 4.5 bathrooms offers direct water access, a private dock and pier, and multiple indoor and outdoor spaces perfect for relaxing, entertaining, and enjoying nature.brbrSet on the edge of the bay, Baywatch is a peaceful and private escape where you can wake up to spectacular sunrises, watch wildlife from your deck, and spend your days crabbing, fishing, or boating right from your backyard.brbrThe SpacebrbrFirst Floor – Waterfront Living at Its BestbrThe main level is thoughtfully designed for both privacy and gathering, with expansive water views throughout:brPrimary suite: King bed, private bath, waterfront balcony, and stunning sunrise viewsbrBedroom 2: Queen bed, private bath, and waterfront balconybrBedroom 3: Queen bed with private bathbrAdditional full hallway bathroom for added conveniencebrThe heart of the home includes a large, fully equipped kitchen with breakfast bar, a spacious dining room with ample seating for family meals, and a bright living room with large windows overlooking Oyster Bay.brbrBedroom 4 (Second Floor): Two twin beds with a half bathbrPerfect for kids, teens, or additional guests seeking their own spacebrbrOutdoor & Waterfront AmenitiesbrbrBaywatch truly shines outdoors, offering everything you need to enjoy waterfront living:brPrivate dock and pier for boating, fishing, and crabbingbrExpansive screened porch overlooking Oyster BaybrMultiple waterfront decks for relaxing, dining, and wildlife viewingbrPanoramic views of the bay from sunrise to sunsetbrGuests also have access to a community boat launch, making it easy to get out on the water and explore.brbrPrime Chincoteague LocationbrbrLocated on beautiful Oyster Bay, Baywatch offers a quiet and scenic setting while still being close to everything Chincoteague Island has to offer. Enjoy nearby restaurants, shops, and local attractions, or take a short drive to Assateague Island’s beaches, nature trails, and famous wild ponies.brbrWhy Guests Love BaywatchbrDirect waterfront location on Oyster BaybrPrivate dock and pier for boating, fishing, and crabbingbrSpacious layout with multiple decks and screened porchbrLarge kitchen, dining, and living areas perfect for groupsbrIdeal for families, couples, and group getawaysbrbrYour Waterfront Escape AwaitsbrbrWhether you're enjoying coffee on the screened porch, watching the sunrise from your balcony, or casting a line from the dock, Baywatch offers an unforgettable Chincoteague Island waterfront experience.brbrCommunity amenities include a shared boat launch for easy access to the water.

Baywatch-Waterfront Home with Screened Porch & Boat Dock

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$249.15

Relax and watch the boats go by from this elegant waterfront townhome.brbrCast a line or set a crab pot from the shared dock, then unwind and take in the peaceful surroundings.brbrThe first floor features a well-equipped kitchen, a cozy living room, a comfortable dining area, and a convenient half bath.brUpstairs are two inviting bedrooms and a shared full bathroom. One bedroom offers a king bed, while the second provides a queen and a double—perfect for families or groups.brbrTwo balconies offer beautiful views overlooking Chincoteague Island and stretching north across Chincoteague Bay.

Caprecia's Castle-Waterfront with Shared Deep Water Dock

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$1283.1

Once a renowned seaside bed & breakfast, Cedar Gables is now the ultimate vacation home. Enjoy stunning views and sunrises over Little Oyster Bay, along with a private pool and hot tub in a screened atrium, a private pier and deep-water boat dock, and waterfront decks and balconies. Every bedroom features a private jet bath, cozy seasonal fireplace, DISH TV, and a DVD player.brbrFirst FloorbrThe Roosevelt Room, just off the foyer, serves as a great room and game room with comfortable seating for TV viewing, a cozy fireplace, pool table, and games—perfect for entertaining guests. The adjacent dining room features a large table overlooking the Roosevelt Room, ideal for gatherings. The kitchen is fully equipped with all the amenities of home, including a breakfast bar, large Jenn-Air stove, wall oven/microwave, and a spacious refrigerator.brbrThe Bistro Porch is a seasonal screened porch with bistro tables for waterfront dining, a cozy sitting area with books, an electric fireplace, and a second beverage fridge for entertaining.brbrThe Original Inn Keeper’s Quarters includes the Assateague Room with a private living area featuring a wet bar, ice maker, wine fridge, beverage fridge, fireplace, sofa, seating area, and piano—all with the home’s best view of Little Oyster Bay. A private office area with a desk adjoins the sea-inspired king suite, which includes a private jet tub bath with a European shower. A full shower bathroom with a full-sized washer/dryer is conveniently located near the jet bath and kitchen.brbrSecond FloorbrRoom 201, a queen bed garden-themed suite, features a private jet bath, loveseat, twin desks, twin closets, and shared balcony access with sunset views. Room 202, the Maverick Suite, has two twin beds, a private jet bath, Little Oyster Bay views, and shared balcony access with Room 201. Room 203, the Neversink Suite, is the most spacious, with a master king bedroom, large master bath with soaking jet tub and separate shower, and a private balcony overlooking the bay—perfect for sunrise views.brbrThird FloorbrRoom 301, the Captain’s Quarters, is a nautical-themed king suite with private jet bath, private balcony, and a Widow’s Watch Tower with bar table and chairs overlooking Little Oyster Bay, offering breathtaking sunrise views.brbrCedar Gables combines historic charm with luxury and modern amenities, making it the perfect destination for an unforgettable getaway.

Cedar Gables-Private Pool, Hot Tub, Deep Water Pier & Dock

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$149.1

Amenities: Central A/C, Cable TV, Microwave, WiFi, Deck, Charcoal Grill, Washer and Dryer. Hypoallergenic linens, towels provided, all pillows (bed pillows and decorative pillows), tissues and toilet paperbrbrCharming 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! New owner has Carbon coconut filter on ceiling fan in bonus room, portable air purifier and plug-in CLARiiON air purifiers. Offering a large deck, and grill and spacious sunroom to relax and enjoy your visit. With this house as well as beach chairs and an umbrella. Hypoallergenic linens, towels provided, all pillows (bed pillows and decorative pillows), tissues and toilet paper. brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less, then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrLINENS AND TOWELS PROVIDEDbrBed Sizes: 1 King, 1 Queen Sleep Sofa, FutonbrbrSaturday Change Overbrbr2026 Off Season Rates $ 100 per night / $ 700 per weekbr2026 Prime Season Rates $ 115 per night / $ 800 per weekbr2026 Pony Swim Week $ 122 per night / $ 850 per week brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Cattail Cottage -Allergy Friendly Home -In Town-LINENS & TOWELS PROVIDED

Chincoteague, Virginia, United States

Bed