
Family-friendly vacation rentals in Chincoteague
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chincoteague
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Maggie’s Cottage on Poplar - Our Happy Place!
Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

Baywatch North-Waterfront & Roaming Ponies
Calender open for super deals on weekly Summer rentals 2026. Lovely space! 2 queen bdrm unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

Dragonfli Bay House on Chincoteague Island
Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayaking on the bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

Little Red House on a Farm - Quiet Rural Waterview
The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

Private romantic pet friendly waterfront cottage
On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Charming Island Home "Sandy Pines"
Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is). The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

Summer's Sea Shanty on Chincoteague Island
Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends. We've worked hard to make this the ideal modern day beach retreat. This home boasts screened in front and back porches, a fire pit, an open/functional floor plan. We're pet and kid friendly with luxury linens and rugs and dish ware... We're proud to be the best of the best on the island. We're centrally located and minutes from Assateague National Seashore.

Heartsong Farmhouse , a nature lover's retreat.
Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

Cozy Barn Loft: Country Views & Central to Beaches
Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

"Jolly"- Houseboat Getaway
#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

The Neigh-Neigh - Location, Location, Location!
Named in honor of the ponies that first put Chincoteague on the map, this charming newly renovated family getaway is walking/biking/and wheeling distance to shops, galleries, restaurants, waterfront park, library, beach, wild ponies, and movie theater. Come relax in a stunning, clean, 2 BR, 2 full BA plus oversized upstairs den with queen and twin beds and a futon bed that comfortably sleeps 8. The amenities and unique offers this place has, is not to be missed.

Ayers Creek Carriage House
Our beautiful carriage house is located on 5 pristine acres along, scenic Ayers Creek, offering year round beauty. Only minutes from Assateague Island, Berlin, and Ocean City. Serene with abundant wildlife. Ideal oasis for outdoor enthusiasts. Worcester County Maryland Rental License #1324
Popular amenities for Chincoteague family-friendly rentals
Family-friendly home rentals with a hot tub

Peace Point - Waterfront, Secluded, Home w/hot tub

The Hideaway at Mill Creek

Peaceful Historic House Near Water, with Hot Tub!

Bay cottage 🏖on the beach. Stunning views🏝

Blue Heron WaterSide

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway
Family- and pet-friendly home rentals

The Crab Shack

Delightful Skoolie Near Bethany Beach

19th Century Coastal Cottage with Modern Amenities

Cattail's Branch

Historic St.Mary's City at the Lazy Bear Cottage

Tent Camp Site 2, Good Earth near Bethany Beach

“Cabana by the Bay”-tiny home on a pier!

Water View Cottage
Family-friendly home rentals with a pool

Peaceful Haven: nature & charming town

The Laughing King Retreat Honeymoon Island Cottage

Nature's retreat @ the Bug-a-Boo. Beaches nearby

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Beautiful Waterfront Home-Private, Clean, Relaxing

Caramar Couples Retreat

Farmhouse located on a horse farm
Quick stats about vacation rentals that are family-friendly in Chincoteague
Total rentals
560 properties
Nightly prices starting at
$56 CAD before taxes and fees
Total number of reviews
14K reviews
Pet-friendly rentals
190 properties allow pets
Rentals with a pool
110 properties have a pool
Rentals with dedicated workspaces
430 properties have a dedicated workspace
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Outer Banks Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- Townhouse rentals Chincoteague
- Beach house rentals Chincoteague
- Rentals with a patio Chincoteague
- Waterfront rentals Chincoteague
- Rentals with outdoor seating Chincoteague
- Pet-friendly rentals Chincoteague
- Beach condo rentals Chincoteague
- Rentals with a firepit Chincoteague
- Cottage rentals Chincoteague
- Rentals with pools Chincoteague
- House rentals Chincoteague
- Rentals with a fireplace Chincoteague
- Apartment rentals Chincoteague
- Rentals with a washer and dryer Chincoteague
- Beachfront rentals Chincoteague
- Condo rentals Chincoteague
- Fitness-friendly rentals Chincoteague
- Rentals with a kayak Chincoteague
- Rentals with beach access Chincoteague
- Family-friendly rentals Accomack County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Chesapeake Bay
- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Assateague Beach
- Jolly Roger Amusement Park
- Peninsula Golf & Country Club
- Assateague State Park
- Bear Trap Dunes
- Northside Park
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Delaware Seashore State Park
- Plantation Lakes Golf and Country Club
- Fenwick Island State Park Beach
- Coin Beach
- Splash Mountain Water Park
- Wallops Beach
- Cripple Creek Golf and Country Club
- Ocean Pines Golf Club
- Parramore Beach
- Guard Shore
- Holts Landing State Park
- Trimper Rides of Ocean City