
Family-friendly holiday rentals in Chincoteague Bay
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Top-rated family-friendly rentals in Chincoteague Bay
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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.

Guesthouse at Vessel Farm & Winery, Waterfront
Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Ocean Pines Retreat
Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Private romantic pet friendly waterfront cottage
On Virginiaâs 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 Natureâs beauty. Be our guest for an unforgettable time on Virginiaâs Eastern Shore!

Beach Highway Hobby Farm
We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

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.

Edgewater Escape - Luxury Bayfront Loft with Porch
You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

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.

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.

Baywatch Upper-Waterfront & Roaming Ponies!
Calender open for super deals on weekly Summer rentals 2026. Beautiful space in and out! Vacation efficiency, situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises. Coastal charm at its finest, there are 2 queen bedrooms and livingroom/breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area, sink and bbq grill.

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 Bay family-friendly rentals
Family-friendly home rentals with a hot tub

Kone Oasis- hot tub, pool, theater/game rm.

Cozy Woodland Cottage

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

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

SaltboxBungalow! HOT TUB! Sunsets! Fully Stocked!

Bay cottage đon the beach. Stunning viewsđ

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
Family- and pet-friendly home rentals

Delightful Skoolie Near Bethany Beach

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

19th Century Coastal Cottage with Modern Amenities

The Bird's Nest at Holly Bluff-Riverfront. Beach.

Summer Perfect, Water Front A-frame on Winery

Stunning private waterfront suite

TooFine Lakehouse, pet friendly waterfront cottage

Newly Renovated 2BR Waterfront Cottage with Dock
Family-friendly home rentals with a pool

Bluewater Couples Escape

Oceanfront Family Oasis: Pool, Beach & Parking!

The Laughing King Retreat Honeymoon Island Cottage

Kits Cottage on "Just Ducky Acres"

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

3 BR Cottage on Mallardee Farm in Williamsburg

Coastal Waterfront 1 Bedroom Cottage

Beautiful Waterfront Home-Private, Clean, Relaxing
Destinations to explore
- Rentals with pools Chincoteague Bay
- Rentals with outdoor seating Chincoteague Bay
- Rentals with a firepit Chincoteague Bay
- Pet-friendly rentals Chincoteague Bay
- Waterfront rentals Chincoteague Bay
- Rentals with a fireplace Chincoteague Bay
- Fitness-friendly rentals Chincoteague Bay
- Rentals with a kayak Chincoteague Bay
- Rentals with a washing machine and dryer Chincoteague Bay
- House rentals Chincoteague Bay
- Rentals with a patio Chincoteague Bay
- Rentals with beach access Chincoteague Bay
- Family-friendly rentals United States