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Holiday rentals with a pool in Chesapeake and Ohio Canal

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chesapeake and Ohio Canal

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.
Cottage in Hamilton
4.95 out of 5 average rating, 424 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Guest favourite
A cozy bedroom features a spacious bed with white bedding and decorative pillows. A sun-shaped mirror hangs on the black accent wall, complemented by stylish lighting. Sheer curtains frame the window, allowing natural light to fill the room, enhancing its inviting atmosphere.
Apartment in Arlington
4.97 out of 5 average rating, 115 reviews

Chic King 1B Met Park•Costco•Min to DC/Metro/Mall

✨Enjoy a relaxing experience located minutes away from DC, Amazon HQ, and surrounded by popular restaurants and Mall. Our stylish home has a dreamcloud like king-size bed, working space, fast free Wi-Fi, and paid on-site garage parking. With all its amenities along with in-unit laundry for an extended stay, you'll feel right at home, Our home is: ❤ in front of Met park ❤ 2 min walk to Whole Foods ❤ 4 min walk to Metro ❤ 5 min from Reagan National Airport (DCA) ❤ 6 min to National Mall/Museums

Top Guest favourite
An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.
Cabin in Bluemont
4.99 out of 5 average rating, 630 reviews

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd acre with access to wooded a trail leads to 5 small cold springs. Amenities 4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail, Shenandoah River, with restaurants, breweries, distilleries and wineries close by! These are rustic not luxurious Cabins

Top Guest favourite
Farm stay in Bluemont
5 out of 5 average rating, 115 reviews

The Cottage at Nestled Inn

Nestled into the Blue Ridge mountains, practically walking distance from Bear Chase Brewery, Twin Oaks Tavern Winery & The Applachian Trail, our home offers you poolside views of our garden, hottub views of the stars, backyard views of our free range chickens & front yard views of our two horses as well as onsite massage therapy, cats & dogs. While being tucked away, we are still just 10minutes from Purcellville or Berryville & 30minutes from Leesburg, Middleburg, Winchester or Harper's Ferry.

Top Guest favourite
The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.
Home in Stevensville
4.97 out of 5 average rating, 130 reviews

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Guest favourite
A spacious dining area is surrounded by large floor-to-ceiling windows, allowing natural light and views of the outdoors. A long wooden table is accompanied by modern chairs and is adorned with plants, enhancing the inviting atmosphere of the space.
Home in Stafford
4.91 out of 5 average rating, 122 reviews

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks

This property sits on the edge of a bluff overlooking the Potomac River and boasts stunning views, both from within and around the home, perfect for bird watching (eagles/osprey), fishing or just relaxing and soaking in nature, just minutes from DC! PLEASE READ CAREFULLY: The pool and spa are CLOSED from LABOR DAY through MEMORIAL DAY. The official open season for pool and spa is between Memorial Day and Labor Day, please confirm availability (if requesting) outside of standard season.

Top Guest favourite
The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.
Home in Perry Hall
4.99 out of 5 average rating, 146 reviews

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Guest favourite
A living area is highlighted by a deep green accent wall and a flat-screen television mounted above a decorative rug. A comfortable sofa with throw pillows sits adjacent to a small dining table with a chair. A potted plant adds a touch of greenery to the space.
Townhouse in Fairfax
4.9 out of 5 average rating, 109 reviews

Cozy Private Entry 1BR1BA Suite Close to GMU & DC

Welcome to your beautiful one-bedroom suite with a modern and cozy interior. This private space features a walkout basement with its own entrance, ensuring privacy and convenience. The suite includes: Bedroom: Comfortable queen-sized bed, large closet Air mattresses: Additional sleeping space if needed. Kitchenette: Fully equipped with essentials . Dining Area Office Desk: Ideal for remote work or study. Updated Bathroom: Includes modern fixtures and amenities. Washer/Dryer

Guest favourite
Home in Adamstown
4.93 out of 5 average rating, 159 reviews

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

Wizards and Humans are invited to experience the magic of Wizard's Escape. A magical home with an escape room twist as you immerse yourself in 2 thrilling themed escape rooms. Perfect for large family gatherings, bachelorette/bachelor/birthdays. Spend hours on our magical scavenger hunt throughout the castle to find the 7 cruxes. Weddings/Events/Pool additional cost. Follow us on Insta for more videos. Book your favorite Gamekeeper's Hut next door for larger parties.

Guest favourite
Home in Waldorf
4.87 out of 5 average rating, 116 reviews

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

Relax with the whole family at this peaceful estate. Newly Remodeled Modern Farmhouse. Enjoy a stylish master bedroom with a double shower and deep freestanding soaker tub. Plenty of areas to relax in and watch movies or enjoy the beauty of the 100-foot-tall trees on the spacious 2-acre lot. Have fun with the Queen-sized bunk beds or if you have a little work to do you can use the home office complete with docking station, web cam and double large screen monitors.

Guest favourite
Guest suite in Annapolis
4.94 out of 5 average rating, 143 reviews

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Top Guest favourite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville
4.99 out of 5 average rating, 360 reviews

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

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