Vacation Rentals By Owner In Chincoteague, VA

Enjoy serene natural vistas from this comfortably appointed home, located in the quiet community of Oyster Bay.brbrThe main bedroom features a king bed and a private bath. Two additional bedrooms—one with a queen bed and the other with a twin and a full bed—share a second full hallway bathroom.brbrThe home offers plenty of space for the family with two separate living areas and a large eat-in kitchen, perfect for meals and gathering.brbrSet in a peaceful location, this lovely home also provides access to the community boat launch and dock for boating and waterfront fun.

Lake Cottage- 3BR | Oyster Bay | Community Boat Launch

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$227.76

Enjoy a limited view of the Assateague Lighthouse along with access to a shared dock and swimming pool. Dock your boat at the shared pier, fish or crab, or simply relax and take in the scenery. The dock is located across the street on a deep-water channel—perfect for boating.brbrThe main level features an open floor plan with kitchen, dining, and living areas, as well as a convenient half bath.brbrUpstairs are two bedrooms, each with its own full bathroom. The first bedroom offers a queen bed and an adjoining bath. The main queen bedroom includes a private bath and a balcony with a view of the Assateague Channel.

Lighthouse Estates #10- Pool | Shared Water Access

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$384.18

Spacious townhome with superb views of Assateague and the iconic Lighthouse. Located on deep water, this home features a private 20' boat dock—perfect for boating, crabbing, fishing, or simply enjoying the waterfront setting.brbrFirst Floor:brThe main level includes a well-equipped kitchen, dining area, half bath, and a beautifully appointed living room with fantastic water views.brbrSecond Floor:brA waterfront king bedroom offers a private balcony overlooking the Channel. An additional bedroom with two extra-long twin beds shares a full hallway bathroom.brbrThird Floor:brThe large primary bedroom features a king bed, a trundle bed (one or two twins), a private bath, and a cozy sitting nook. The private balcony on this level provides the best lookout point over the Channel—an ideal spot to watch the sunrise over Assateague Island.

Lighthouse Lookout- 3BR | Boat Dock | Waterfront

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Exceptional(3)

$155.18

Cozy and comfortable, this charming cottage is nestled in a tranquil setting, yet just a short walk from downtown. The larger bedroom features a queen bed, while the second bedroom has bunk beds, sharing a full bathroom. Enjoy a private screened porch, an outdoor shower for rinsing off after a day at the beach, and a firepit for cozy evenings under the stars. Deer Track offers a welcoming layout, perfect for a family vacation.

Deer Track-Cozy Cottage Close to Town. Fire Pit.

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$398.87

Welcome to Heron Point, a bright and beachy retreat located in the desirable Oyster Bay community on Chincoteague Island. This family-friendly home offers a perfect mix of comfort, space, and amenities, making it ideal for a fun and relaxing coastal getaway.brbrWhile not directly canal-front, Heron Point is just steps from the community boat launch and dock, giving you easy access to the water for kayaking, boating, and exploring the beautiful surrounding area.brbrThe SpacebrbrMain Level – Comfortable Coastal LivingbrThe main level is open, inviting, and perfect for gathering after a day of island adventures:brbr* Cozy living room with a seasonal fireplacebr* Fully equipped kitchen for preparing meals and snacksbr* Dining area for family meals and game nightsbr* Primary bedroom with king bed and private bathroombr* Queen bedroom and full bedroom sharing a hallway bathroombrbrLower Level – Fun for EveryonebrThe basement level is designed with families in mind:brbr* Game room with foosball table and entertainment spacebr* Additional sleeping area, perfect for kids or extra guestsbr* Screened porch for relaxing and enjoying the coastal breezebrbrOutdoor Living & AmenitiesbrHeron Point is packed with features to help you make the most of your time outdoors:brbr* Kayaks and a tandem kayak for exploring nearby waterwaysbr* Bikes for cruising around the neighborhood or into townbr* Easy access to the community boat launch and dockbr* Peaceful Oyster Bay setting perfect for walking and enjoying naturebrbrPrime Chincoteague LocationbrLocated in the quiet Oyster Bay community, Heron Point offers a relaxing setting while still being close to local restaurants, shops, and attractions. A short drive takes you to Assateague Island, where you can enjoy beaches, wildlife, and the famous wild ponies.brbrWhy Guests Love Heron Pointbrbr* Bright, beachy home with plenty of space for familiesbr* Game room and extra sleeping space for kidsbr* Kayaks, tandem kayak, and bikes includedbr* Walkable access to community boat launch and dockbr* Quiet neighborhood close to Chincoteague attractionsbrbrYour Chincoteague Getaway Starts HerebrWhether you're planning a family vacation, outdoor adventure, or relaxing escape, Heron Point has everything you need for a memorable stay.brbrBook now and enjoy the best of Chincoteague Island living.brbrHeron Point also boasts excellent outdoor living amenities, including kayaks, a tandem kayak, and bikes, making it easy to enjoy both the water and the surrounding area.

Heron Point | Beach Home w/ Kayaks, Bikes, Game Room, Screened Porch & Boat Launch

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$204.64

Beautifully refurbished traditional home with a charming front porch in Chincoteague’s Historic Downtown.brbrThe first floor features a full kitchen with laundry, dining area, living room, and a convenient half bath. Both bedrooms—each with a queen bed—and a shared full bathroom are located on the second floor. Original hardwood floors have been lovingly restored throughout the home.brbrStroll across to the town dock or enjoy the beautiful waterfront downtown park. Shops and restaurants are just steps away. The home also offers a small yard situated on a quiet lane.

Lewis House- 2BR Cottage | Historic Downtown

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$556.44

Escape to the peaceful shores of Chincoteague Island and experience true waterfront living at Horsin’ Around, a charming bayfront retreat on Oyster Bay. With your own private dock just steps away, this home is perfect for boating, crabbing, fishing, or simply soaking in the coastal beauty.brbrWake up to breathtaking sunrises from the front upper deck, coffee in hand, as the bay comes to life. Spend your days on the water or exploring nearby attractions, then return to a comfortable, thoughtfully designed home that makes relaxing easy.brbrInside, the home offers a bright and inviting living space with a fully equipped kitchen, dining area, and a cozy, tastefully furnished living room. There are three bedrooms, including a king bedroom with a newly remolded full bathroom in hall, a queen bedroom, and a twin bedroom with two beds. The queen and twin bedrooms both open onto an upper canal front screened porch, providing a peaceful spot to unwind and enjoy the view. A second full bathroom is located in the hallway, and a small walk-through den includes a double sleep sofa for additional guests.brbrHorsin’ Around is designed to make the most of its waterfront setting, with a private dock offering direct access to the bay. The spacious front deck is perfect for outdoor dining and features a gas grill alongside scenic water views. Beneath the home, a covered area includes an outdoor shower, half bath, clean-up station with sink, laundry room, picnic table, and a swing - ideal for relaxing or rinsing off after a day on the water. The basement game room adds extra entertainment for guests of all ages.brbrThis home is also pet-friendly, allowing up to two pets for an additional fee, so you can bring your furry companions along for the adventure.brbrEnjoy a quiet and private setting while staying close to everything Chincoteague has to offer. A short drive brings you to the beaches and natural beauty of Assateague Island, where you can experience wildlife, coastal landscapes, and the island’s famous wild ponies.brbrWhether you’re casting a line off the dock, enjoying a meal on the deck, or relaxing with family and friends, Horsin’ Around offers the perfect setting for a memorable waterfront escape.

Horsin Around | 3BR with Private Dock, Deck and Pet-Friendly

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$382.77

Splendid home located in the serene Oyster Bay community, featuring exceptional decor throughout. A private boat dock right at your door and a nearby community boat launch make it easy to enjoy the water, while every room offers views of the canal or natural surroundings.brbrThe first floor includes a beautiful main bedroom with a queen bed and private bath, as well as spacious living and dining rooms, a fully equipped kitchen, and a convenient half bath. Upstairs, two additional bedrooms—one with a queen and one with two twins—share a full bathroom, and each bedroom has its own private balcony.brbrNestled in a natural and tranquil setting, this home is perfect for a relaxing waterfront getaway.

Dee's Nest- Canalfront in Oyster Bay with Boat Dock

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$466.95

Experience the beauty of Chincoteague waterfront living at this charming home overlooking Little Oyster Bay. With a private deep water dock, stunning water views, and peaceful surroundings, this property is perfect for boating enthusiasts, anglers, and families looking for a relaxing coastal escape.brbrStart your mornings with breathtaking sunrises over the bay, spend your days fishing, crabbing, or boating from your private pier, and unwind in the evening as the water reflects the changing colors of the sky. This is the perfect blend of comfort, convenience, and waterfront charm.brbr---brThe SpacebrbrThe first floor offers a warm and inviting layout:brbrEat-in kitchen fully equipped for preparing mealsbrComfortable living room perfect for relaxing after a day on the waterbrBedroom with queen bed and beautiful water viewsbrAdditional sleeping area with a double futon in the rear living spacebrFull hallway bathroom for conveniencebrbrUpstairs, you’ll find:brbrWaterfront king bedroom with serene bay viewsbrWaterfront queen bedroom also overlooking the waterbrShared full bathroom easily accessible from both bedroomsbrbrThis flexible layout makes the home ideal for families or small groups, offering both shared spaces and private retreats.brbr---brbrOutdoor & Waterfront AmenitiesbrbrPrivate deep water dock—perfect for docking your boatbrExcellent spot for fishing, crabbing, and kayakingbrUnobstructed views of Little Oyster BaybrIdeal setting for sunrise watching and wildlife viewingbrPeaceful, scenic environment away from the crowdsbrbr---brbrPrime Chincoteague LocationbrbrLocated in a quiet area of Chincoteague Island, this home offers waterfront tranquility while still being close to local restaurants, shops, and the natural beauty of Assateague Island. Enjoy easy access to beaches, wildlife, and outdoor adventures.brbr---brbrWhy Guests Love This HomebrbrPrivate deepwater dock for boating, fishing, and crabbingbrStunning sunrise views over Little Oyster BaybrMultiple water-view bedroomsbrFlexible sleeping options for families or groupsbrQuiet, relaxing waterfront setting near island attractions

Great Blue- 3 BR I Waterfront with Private Pier & Boat Dock

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Exceptional(32)

$189.26

Amenities: Central A/C, TV, DVD, VCR, WiFi, W/D, Dishwasher, Microwave, Gas Grill, 2 Decks, Large Back Yard, Water ViewbrbrEnjoy the water view from this immaculate home offering spacious rooms and a quiet location off of Main Street. All bedrooms are on the same level. Spread out in the two separate living rooms and two lovely porches. Plenty of space in the large dining room for the whole family to gather for meals.. 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 LINENS AND TOWELS ARE PROVIDED SO BRING YOUR OWN OR CALL TO RENT THEM. brbrbrBed Sizes: 1 King, 2 Queen, 1 Double FutonbrbrSunday Change Overbrbr2026 Prime Season Rates $ 854 per week / $ 122 per night 3 night minimumbr2026 Prime Out Rates $ 658 per week / $ 94 per night 3 night minimumbrbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Decolores - Water View - Close to town -Gas Grill - Deck NO LINENS PROVIDED

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$226.53

Discover Fowling View, a charming waterfront townhouse nestled in a quiet, natural setting on Chincoteague Island, Virginia. Perfect for birdwatchers, nature lovers, and families, this home offers serene wetland and sunset views, direct access to the water, and a relaxing coastal atmosphere.brbrStep out from the screened-in porch off the living room to the shared pier and crabbing dock—ideal for crabbing, kayaking, or simply enjoying the peaceful surroundings. Whether it’s morning coffee watching the birds or evening sunsets over the wetlands, Fowling View brings nature right to your doorstep.brbrThe SpacebrbrThe first floor features:brbrEat-in kitchen fully equipped for meal prep and family gatheringsbrLiving room that opens to the screened porch with water viewsbrLaundry area and convenient half bathbrbrUpstairs, the townhouse offers comfortable sleeping arrangements:brbrFirst Bedroom: Queen bed, shared hallway bathroom, and screened balcony with stunning wetland and sunset viewsbrSecond Bedroom:Double bed and twin bed with private bathbrbrThe layout provides both privacy and flexibility, making it perfect for families, couples, or small groups.brbrOutdoor & Waterfront AmenitiesbrbrShared pier and crabbing dock for fishing, crabbing, or launching a kayakbrScreened-in porch and balcony with panoramic views of the wetlandsbrRelaxing natural setting with abundant wildlife and birdwatching opportunitiesbrPerfect for watching sunsets.brbrbrPrime Chincoteague Island LocationbrbrLocated in a quiet corner of Chincoteague, Fowling View is just minutes from local restaurants, shops, bike trails, and the beaches and wildlife of Assateague Island. This combination of waterfront living and convenience makes it an ideal base for your island getaway.brbrbrWhy Guests Love Fowling ViewbrbrWaterfront townhouse** with shared pier and crabbing dockbrScreened porch and balcony with wetland and sunset viewsbrComfortable, family-friendly layout with two bedrooms and 2.5 bathsbrAbundant birdwatching and wildlife opportunitiesbrQuiet, natural setting near Chincoteague attractionsbrbrBook your stay at Fowling View and enjoy the tranquility, sunsets, and waterfront charm of Chincoteague Island.

Fowling View | Townhouse w/ Pier, Crabbing Dock & Sunset Views

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Exceptional(3)

$281.93

Wake up to tranquil waterfront living at Fiddler Bay #6, a beautifully maintained townhome offering direct bay access and unforgettable coastal scenery. Located on Chincoteague Island, this vacation rental is ideal for guests seeking boating, nature, and relaxation. A shared dock allows easy access for kayaking, canoeing, crabbing, and fishing, while the peaceful channel provides ever-changing water views throughout the day.brbrThe main level features an inviting open layout with comfortable seating, abundant natural light, and water views that bring the outdoors in. The kitchen is fully stocked for home-cooked meals, seafood feasts, or casual breakfasts before a day at the beach. A dining area and half bath add convenience for groups and extended stays.brbrUpstairs, two spacious bedrooms each include a private full bathroom, offering comfort and privacy. The primary suite includes a king bed and private balcony overlooking the water—perfect for unwinding after a day of exploring. The second bedroom offers a queen bed with trundle, making it family-friendly. Linens and bath towels are provided.brbrJust a short drive to Assateague Island Beach, the wild ponies, and the Chincoteague National Wildlife Refuge, this home is perfectly located for beach vacations, outdoor adventures, and memorable island escapes.

Fiddler Bay #6-End Unit Waterfront Townhome with Shared Crabbing Pier

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Exceptional(4)

$298.63

Well-appointed and comfortable, this townhome offers stunning views of Assateague and the Lighthouse. Enjoy the shared pier for canoeing, crabbing, or simply taking in the water.brbrThe first floor features a living room, kitchen, and dining area, along with a private den that includes a queen sleeper sofa and a full bathroom with a shower stall. Upstairs, two bedrooms each offer a private bathroom. The rear bedroom is waterfront with a king bed and a balcony overlooking Assateague Channel, while the front bedroom features a queen bed.brbrBring your kayaks—this location is perfect for enjoying the water and the natural beauty of the area.

Fiddler Bay #5- Waterfront Townhome w/ Shared Crabbing Pier

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$290.7

Situated on the edge of Oyster Bay, this charming home offers stunning sunrises and beautiful views of the bay and the surrounding natural setting. Oyster Bay is a quiet, peaceful community, and the home itself is very comfortably appointed with artistic decor throughout. A bulkheaded shoreline provides easy access for fishing and crabbing.brbrThe second floor features a bedroom with a queen bed and another with a full-size bed, connected by a Jack and Jill bathroom. There’s also a kitchen, dining, and sitting area on this level.brbrOn the first floor, the living room includes a TV, and there’s a bedroom with one full and two twin beds, along with a full bath. A cozy porch bar leads out to a patio and the nicely landscaped bayfront yard, perfect for enjoying the scenery.brbrExperience amazing views of the bay, nature, and unforgettable sunrises from this peaceful retreat.

Edgewater- Waterfront on Oyster Bay.

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Exceptional(2)

$228.84

Superbly appointed duplex unit located on a quiet cul-de-sac, Drop Anchor is an extremely comfortable home with charming beachy decor. Enjoy relaxing on the screened porch, rear deck, or in the grassy yard.brbrThe first floor features a well-equipped kitchen, living room, and dining area, along with one bedroom with a king bed and a full hall bathroom. Upstairs, two additional bedrooms include a king and two twins, sharing a full hallway bath that is also accessible from the primary king bedroom.brbrThe owner offers a 10% Military Discount, making this a perfect getaway for families or groups seeking comfort and convenience.

Drop Anchor-Close to Memorial Park, Quiet Neighborhood

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Exceptional(6)

$473.07

Spacious Private Yard | Screened Porch/Game Room | Pets Welcome w/ Fee | WFH FriendlybrbrA blissful island escape awaits at this Chincoteague vacation rental! With its perfect combination of historic charm and boutique finishes, this 3-bedroom, 1.5-bath home is ideal for enjoying a unique coastal getaway with your loved ones. Spend time in the cozy backyard, relax on serene shores, or watch the wild ponies at Chincoteague Island National Wildlife Refuge!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 twin bunk bedbr- Bedroom 3: 2 twin bunk bedsbr- Additional Sleeping: 2 twin air mattressesbrbrINDOOR LIVINGbr- Flat-screen TVs w/ cable, booksbr- Beautiful coastal artworkbr- Boutique accent furnishingsbr- Laptop-friendly workspacesbr- Sunroom w/ seating, dining areabrbrOUTDOOR LIVINGbr- Beach chairs & umbrellabr- Outdoor showerbr- Screened porch w/ ping-pong table & foosball tablebr- Pergola, outdoor dining areabrbrKITCHENbr- Center island backed w/ wine case wood, new countertopsbr- Refrigerator, stove/oven, dishwasherbr- Drip coffee maker, toaster oven br- Cooking basics, spices, trash bags/paper towels, dishware & flatware brbrGENERALbr- Central heating & A/C br- Washer/dryer, laundry detergent, iron/board br- Linens/towels, beach towels, complimentary toiletries, hair dryer br- Free WiFibrbrFAQbr- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 2-story home, exterior stairs required to enterbr- Half bathroom on 1st floor, all bedrooms on 2nd floorbrbrPARKINGbr- Crushed seashell driveway (2 vehicles)br- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Peaceful neighborhood within 2 miles of shops & restaurantsbr- 3 miles to Assateague Island National Seashore, Maui Jack's Waterpark & Museum of the Chincoteague Islandbr- 4 miles to Chincoteague National Wildlife Refuge: beaches, lighthouse, pony viewingbr- 6 miles to Assateague Beachbr- 100 miles to Norfolk International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires exterior stairs to enter. While it offers a half bathroom on the 1st floor, interior stairs are required to access the bedrooms on the 2nd floor

2 Mi to Downtown: Tranquil Abode in Chincoteague!

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$264.98

Amenities: Central A/C, TV, W/D, Microwave, Dishwasher, Screened PorchbrbrEnjoy your stay in this newly renovated historic island home locally known for its three majestic Loblolly Pines. Enjoy relaxing or eating outdoors in the screened-in porch that offers plenty of space for your group to spread out. Centrally located, Three Pines is just a walk or bike ride away from everything Chincoteague has to offer.brbr~This is a pet-free home~brbrOn the ground floor of this home, you'll find an open concept living/dining room, a small full bath with shower and washer/dryer combo, and an airy kitchen. Down just three steps from the kitchen, the large screened-in porch offers plenty of seating and another dining space.brbrThe three bedrooms and second full bath of this home are upstairs. The house comfortably sleeps eight, although trundles under the double beds allow flexibility in sleeping arrangements.brbrGuests will have access to the entire home, fully screened-in porch area, fenced-in backyard, and large front yard. There's plenty of parking on the property.brbrBed Sizes: 1Q, 2D, 4Tbrbr2026 $ 1393 weekly/ $ 199 nightly. ( 3 night minimum excluding Pony Swim Week ) brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Three Pines- Screen Porch - Close to Town - Newly Renovated

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$519.89

Baywatch House is a super clean waterfront home ideally located in a quiet and isolated location, perfect for a Chincoteague Island vacation. House borders a horse pasture where Chincoteague ponies and other horses roam.br 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 possiblebrMain 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 shared with BR #2. The 3rd 3 piece Bathroom has a shower and is downstairs next to the laundry room. Nice bed linens, towels, washcloths, hair dryers and bath soaps are provided. Starter paper products are provided for both the kitchen and baths. Mr. Coffee type coffee maker is in the kitchen. Town is a 7 minute drive from the house.brbrOversized Washer & Dryer with laundry detergent are located on the ground floor. brWireless Internet , Satellite TVbrBeach chairs, beach towels, cooler are provided.

Waterfront 5 star: North End of Island. Private property borders Pony pasture!

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Exceptional(25)

$277.6