
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.

SeaGate Serenity | Oceanfront Condo with Balcony
Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

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.

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

Cozy beach home away from home!
Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

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.

Caramar Couples Retreat
This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

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

2 BR Ocean Front Condo w/Pool, Expansive Views

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

Campfire Bliss at the Beach

Ocean Palms II - Renovated, Ocean Block, Midtown

Ocean Pines Retreat with Beach Club
Condo rentals with a pool

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck

Steps from Seacrets Beach House Getaway

Oceanfront Family Oasis: Pool, Beach & Parking!

Downtown Condo, Parking, Walk to Beach & Boardwalk

Love Above the Waves-OceanView/Rooftop Heated Pool

Ocean Pines Yacht Club Condo Waterview

Beachfront with a View and Amenities Galore

Renovated Oceanside Modern Boho Beach Retreat
Other holiday rentals with a pool

Stunning Home w/Private Pool, Garden & Firepit

Bayside Bungalow - Waterfront

The Homestead at Sugar Water Manor Farm Stay

Custom waterfront home by Seaside Vacations

Floating Bungalow - Marina View

Luxe Bay Hideaway

Fenwick Island Sunset Retreat

SuperHost! Amazing OceanFront View with 2 Pools!
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 $112 AUD 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

Wi-Fi availability
20 of Chincoteague Island holiday rentals include Wi-Fi 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
- Family-friendly rentals Chincoteague Island
- Rentals with a fire pit Chincoteague Island
- Pet-friendly rentals Chincoteague Island
- House rentals Chincoteague Island
- Rentals with beach access Chincoteague Island
- Rentals with a patio Chincoteague Island
- Rentals with a washing machine and dryer Chincoteague Island
- Waterfront rentals Chincoteague Island
- Rentals with outdoor seating 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
- Fenwick Island State Park Beach
- Bethany Beach Boardwalk
- Ocean Pines Golf Club
- Roland E Powell Convention Center
- Trimper Rides of Ocean City
- Old Pro Golf
- Salisbury Zoo
- Bear Trap Dunes
- Layton's Chance Vineyard and Winery
- Baja Amusements
- NASA’s Wallops Flight Facility Visitor Center





