
Holiday rentals with a pool in Accomack County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Accomack County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Island Creek Retreat - Great Views, Pool, Pier
Just a few miles from Chincoteague National Wildlife Refuge & Assateague Beach. Beautiful marsh & wetland views. Shared private pier is perfect for crabbing & birdwatching. Great location - walk or bike to shops, restaurants, water park & much more! Spend the day at the shared private pool. This 2nd floor unit has a bedroom w/ king bed, kitchenette with 2 burner stove top, microwave, & full size fridge. Spacious living room w/ queen sleeper & desk. Access the full bathroom from the living area.

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.

Belle Haven’s Bliss
Experience Belle Haven’s Bliss, stay in a 25 foot Airstream on private wooded property with access to a swimming pool in the backyard and tennis court in the front! Your very own retreat that’s only minutes from downtown Exmore. We are located in between both Cape Charles and Onancock, about 25 minutes from each. Chincoteague is 50 minutes to the North. We have many options for entertainment here on The Shore and property. The host family stays on the same property and is available as needed.

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.

Leatherbury Point
Waterfront guest house on Onancock Creek, five minutes from the charming town of Onancock, Virginia. Designed by architect Lewis Rightmier, the home enjoys spectacular water views from every room, a swimming pool, a dock with two boat slips for kayaking, fishing, and crabbing. Perfect for the active outdoors person, or ideal for relaxing in the Adirondack chairs and watching the sailboats come in and out of the creek. For events and festivities, browse the ESVA Chamber website.

Waterfront Chincoteague Island
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.

Flamingo Villa
The Flamingo Villa @ The Reef Features two bedrooms upstairs and 1/2 bath. Each bedroom has a Queen Bed Downstairs has a fully equipped kitchen, bathroom with a shower and a sleeper sofa in the living room The Reef Vacation Villas has an indoor pool, bikes, stand up paddle boards, corn hole, and Two passes to MAUI JACKS WATERPARK just a short walk away Stay with us and beat the traffic to the beach since we are located just over a half mile from the beach

Key Lime Cottage
Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

Harbor Master
Relax and enjoy the views at this unique waterfront getaway! This home at the mouth of Chesconessex Creek and Chesapeake Bay is an extremely private location with the convenience of being 8 minutes from the historic and fun town of Onancock, VA. Covered porches provide lots of outdoor spaces. Three level living allows for separate living spaces. Home has lots of stairs, so may not be appropriate for everyone.

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.

The Porter's Barn | Waterfront w/ Dock + Fire Pit
Welcome to "Porter's Barn at The Creek!" - a fabulous vacation flat located on Chincoteague Island! Enjoy all the fine features this charming cottage has to offer, and remember, you're renting the *entire* place which means you don't have to share! After all, this is... #WhereGreatVacationsHappen ...on Virginia's Eastern Shore!
Popular amenities for Accomack County rentals with a pool
House rentals with a pool

Captain Morgan’s

Campfire Bliss at the Beach

Bayfront Retreat w/ Game Room + Outdoor Pool!

Coastal Crab by Seaside Vacations & Sales

Salty Paws - A Captain's Cove Vacation Home

Octopus's Garden by Seaside Vacations & Sales

Seaside Rendezvous Chincoteague

Dog-Friendly Family Retreat Near Chincoteague Bay!
Apartment rentals with a pool

Assateague Inn 203 by Seaside Vacations & Sales

Walk to Main St: Condo w/ Pool Access in Crisfield

Assateague Inn 102 by Seaside Vacations & Sales

Sunset Bay Villa 209 by Seaside Vacations & Sales

Sunset Bay Villa 306 by Seaside Vacations & Sales

Another Day in Paradise

Assateague Inn 110 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Other holiday rentals with a pool

Black Skimmer by Seaside Vacations & Sales

Oyster Cottage

Vast Views - Pet friendly; Shared pool!

Coves Point by Seaside Vacations & Sales

Assateague Inn 206 by Seaside Vacations & Sales

Your Song by Seaside Vacations & Sales

Coconut Waterfront Cottage

Shellfish Time by Seaside Vacations & Sales
Destinations to explore
- Hotel rooms Accomack County
- Rentals with a fireplace Accomack County
- Beachfront rentals Accomack County
- Flat rentals Accomack County
- Pet-friendly rentals Accomack County
- Family-friendly rentals Accomack County
- Rentals with a patio Accomack County
- Rentals with a kayak Accomack County
- Rentals with a washing machine and dryer Accomack County
- Townhouse rentals Accomack County
- Apartment rentals Accomack County
- Rentals with lake access Accomack County
- Rentals with outdoor seating Accomack County
- Rentals with a firepit Accomack County
- House rentals Accomack County
- Rentals with pools Virginia
- Rentals with pools United States




