
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.

Assateague Vista- Waterviews, Pool, Shared Dock
Just a few miles from Chincoteague National Wildlife Refuge & Assateague Beach. Nicely appointed town home with pool and dock access. Great views of Assateague Island. Shared boat dock, also great for crabbing. Comfortable living room, dining room, kitchen, and half bath are downstairs. Both bedrooms are upstairs. Main queen bedroom has a private bath and balcony overlooking the pool, Assateague Channel & the Lighthouse. The second bedroom has a queen bed and an adjoining hallway bath.

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).

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-Bedroom Oceanfront – Pool, Xbox, Pickleball, Gym, Wi-Fi
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!

Coastal Retreat near the beach
Kick back and relax in this calm, stylish space just 15 minutes from Ocean City MD beaches. The unit has marsh and water views of Assawoman Bay/Manklin Creek. Located across the bay from Ocean City , MD you are close to the action but can retreat back to a quiet sanctuary when you are looking for some relaxation away from the beach crowds. If you like nature, frequent visitors include, deer, fox, blue heron, egrets, bald eagles, owls and many other birds.

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

Bayfront Modern Retreat • Dock, Kayaks, Views
Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.
Popular amenities for rentals with a pool near Chincoteague Island
House rentals with a pool

Ocean Pines 2BR 1BA Cottage with Fire Pit

The Puskar’s Landing

Cozy beach home away from home!

Private pool, waterfront, kayaks, bikes, firepits!

Harbor Master

Serene Family Getaway | OC & Assateague Adventures

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

Quiet 3BR Coastal Home Minutes to Bethany Beach
Condo rentals with a pool

Boutique Moments OC • Pool • Walk to Boardwalk

Downtown Condo, Parking, Walk to Beach & Boardwalk

Love Above the Waves-OceanView/Rooftop Heated Pool

Water view at Ocean Pines Yacht Club Condo

Designer Oceanfront Condo | Pool, Hot Tub & Deck

Sunset Pearl

Modern Coastal Calm 2 BR Retreat + Pool

Direct Ocean Front 1BR Condo indoor/outdoor pools
Other vacation rentals with a pool

Bayside Bungalow - Waterfront

Year Round Playground - Rare Rustic-Modern Getaway

Bright Oceanside Condo with Pool - Ocean City, MD

Floating Bungalow - Marina View

An Assateague Adventure

3BR|Game Room|Pool|Outdoor Sports|3 miles to Beach

The Shore on 54

Artist Windmill Pt Condo Sunset Pool Relaxation
Quick stats about rentals with a pool near Chincoteague Island

Total vacation rentals
Explore 20 vacation rentals in Chincoteague Island

Nightly prices starting at
Chincoteague Island vacation rentals start at ﺩ.ﺇ 294 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 vacation 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
- House rentals Chincoteague Island
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- Waterfront rentals Chincoteague Island
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- Rentals with pools Chincoteague
- Rentals with pools Accomack County
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- Rentals with pools United States
- Chesapeake Bay
- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Assateague State Park
- Bethany Beach Boardwalk
- Northside Park
- Jolly Roger Amusement Park
- Delaware Seashore State Park
- Fenwick Island State Park Beach
- Ocean City Boardwalk
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Old Pro Golf
- Trimper Rides of Ocean City
- Salisbury Zoo
- Bear Trap Dunes
- Holts Landing State Park
- NASA’s Wallops Flight Facility Visitor Center
- Layton's Chance Vineyard and Winery
- Jolly Roger at the Pier
- Splash Mountain Water Park





