
Home rentals with a pool near Chincoteague Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Chincoteague Island
Guests agree: these stays are highly rated for location, cleanliness and more.

Nature's retreat @ the Bug-a-Boo. Beaches nearby
We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

Hidden Gem! Relax & Visit Chincoteague Island
Experience comfort in our cozy, newly built 2-story home with central air/heat. Nestled in a gated campground where best mode of transportation is golf cart! Home has 3 bedrooms, 2 bathrooms, jacuzzi jet tub, oversized sectional sofa, smart TVs W/ FUBO, MASN and movie channels, high-speed Wi-Fi, DVD/VHS movie collection, board games, fully equipped kitchen with basic pantry items, dining area, washer/dryer. Relax on the private back deck/yard featuring a Weber gas grill, fire pit, and hammock.

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.

Campfire Bliss at the Beach
Relax and Enjoy the outdoors with the whole family at this peaceful place to stay. 2 Bedroom, 1.5 bath Cottage in Trails End Campground located in Horntown Virginia on Chincoteague Bay. Sleeps 6 , includes outdoor fire pit, boat launch and onsite restaurant and grocery store. Must bring own bath towels & beach towels and linens and blankets and life jackets. Must wash dishes prior to check out. NO SMOKING! NO VAPING Door code 1 day prior NO PETS! MAX 2 vehicles MAX Guest 6

Big Cozy Loft Overlooking the Farm and River
The cozy loft is located above the apiary workshop. It is a spacious, kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens. Designed for a true retreat, there is no WiFi, TV, or smoking. For breakfast, travel on over to Sugar Water Restaurant to have a free breakfast with coffee, tea, juice, and more. The Loft includes a small refrigerator plus coffee and tea essentials. Please note: children are not permitted.

Direct Oceanfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Farmhouse located on a horse farm
Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Year Round Playground - Rare Rustic-Modern Getaway
Enjoy best of Eastern Shore living in this unique property that provides privacy & exciting amenities for everyone: POOL, 7 PERSON HOT TUB, OUTDOOR KITCHEN, REC ROOM, FISHING, W/GOLFING & BEACHES nearby! Newly renovated 3BR/2.5BA offers guests an opportunity to have in-the-woods feelings w/o sacrificing comfort. Escape the city rushes on a rare waterfront property w/private dock on East Creek leading out to the bay! Don't miss out on Insta-worthy photo ops! BOOK NOW!!!

Sunset Bay Villas 219 waterfront condo
Amazing views- Welcome Bird Watchers, Nature and Beach Lovers! Designer condo with direct views of the Intracoastal Waterway Chincoteague Channel and Wallops Long term rental from October-May with government per diem per person and special offers for long term occupancy. Max. occupancy per Chincoteague town fire code is 8. This includes adults, children (2 and older) and infants (children under two). Government ID issued required to be shown on or before check in date.

2 BdrmOceanfront-Pool, Xbox, Pickleball, Gym, WiFi
Wake up to panoramic ocean views at Blue Wave, a newly renovated 2BR/1.5BA oceanfront condo in the premier Golden Sands Resort! Sleeps 6 with king bed, queen bed, and queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, and seasonal tiki bar. Relax with a Smart TV + Xbox Series S with Gamepass! Steps to the beach, close to Northside Park, great restaurants, and the Ocean City Boardwalk!

Cedar Gables - Waterfront, Pool, Hot Tub, Dock
Just a few miles from Chincoteague National Wildlife Refuge & Assateague Island Beach, Cedar Gables has everything you are looking for in a Chincoteague Island home! Enjoy the ease and convenience of a central waterfront location. Each bedroom has a seasonal fireplace & private bath w/ deep tub. Lounge outside by the private pool (seasonal), hot tub (year-round) & tiki-bar in screened atrium. Private, deep water pier & boat dock is perfect for crabbing & fishing.

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU
BEFORE BOOKING: Pool will be open 4/05/26 Unless PRIOR AUTHORIZATION….. NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your party are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key
Popular amenities for rentals with a pool near Chincoteague Island
House rentals with a pool

Cozy beach home away from home!

Harbor Master

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

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

Cozy Beach Escape Mallard Lakes Resort Amenities

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

Ocean Palms II - Renovated, Ocean Block, Midtown

Mosaic Life Escapes -Bayfront Million Dollar Views
Apartment rentals with a pool

Ultra Luxe Oceanfront Escape w/Breathtaking Views!

Boutique Moments OC • Pool • Walk to Boardwalk

Oceanfront•Pool•Private Balcony w/Sunrise Views

Downtown Condo, Parking, Walk to Beach & Boardwalk

Oceanfront Bldg.| 2 pools | Tennis | Game Room

Love Above the Waves-OceanView/Rooftop Heated Pool

Ocean Pines Yacht Club Getaway Waterview

Caramar Couples Retreat
Other holiday rentals with a pool

Vast Views | Pool, Pier + Lighthouse Views

Bayside Oasis *In-Ground Pool*Hot Tub*Huge Yard*

Custom waterfront home by Seaside Vacations

Floating Bungalow - Marina View

BayFront Villa on Chesapeake, Newly Renovated Pool

Sand Dollar Villa

Pines & Sea A-Frame • Coastal & Cozy Stay

Knot Stressed in Captain’s Cove
Quick stats about rentals with a pool near Chincoteague Island

Total holiday rentals
Explore 20 holiday rentals in Chincoteague Island

Nightly prices starting at
Chincoteague Island holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 1,380 verified reviews to help you choose

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Chincoteague Island holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chincoteague Island rentals

4.6 Average rating
Chincoteague Island stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Rentals with a fireplace Chincoteague Island
- Waterfront rentals Chincoteague Island
- Family-friendly rentals Chincoteague Island
- Rentals with a firepit Chincoteague Island
- Pet-friendly rentals Chincoteague Island
- House rentals Chincoteague Island
- Rentals with beach access Chincoteague Island
- Rentals with outdoor seating Chincoteague Island
- Rentals with a washing machine and dryer Chincoteague Island
- Rentals with a patio Chincoteague Island
- Rentals with pools Chincoteague
- Rentals with pools Accomack County
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Ocean City Beach
- Ocean City Boardwalk
- Ocean City Boardwalk
- Assateague Island National Seashore
- Northside Park
- Assateague State Park
- Jolly Roger Amusement Park
- Delaware Seashore State Park
- Bethany Beach Boardwalk
- Fenwick Island State Park Beach
- Ocean Pines Golf Club
- Roland E Powell Convention Center
- Old Pro Golf
- Trimper Rides of Ocean City
- Salisbury Zoo
- Bear Trap Dunes
- Holts Landing State Park
- NASA’s Wallops Flight Facility Visitor Center
- Baja Amusements
- Layton's Chance Vineyard and Winery





