Holiday rentals with a pool in Chesapeake and Ohio Canal

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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!

Top guest favourite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in St. Michaels
4.97 out of 5 average rating, 197 reviews

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

Guest favourite
A spacious living area features a grey sectional sofa that includes a chaise lounge and a round glass coffee table. The wall behind is adorned with a modern geometric design, complemented by a circular mirror. Natural light fills the room through the large window.
Flat in Pentagon City
4.92 out of 5 average rating, 101 reviews

Costco Met Park•King bed•Gym• 6 Min to Metro/DC

✨ Enjoy a relaxing experience located minutes away from DC, Amazon HQ, and surrounded by popular restaurants and Mall. Our stylish apartment includes a super comfy king-size bed, workspace, fast free Wi-Fi, and paid on-site parking. The kitchen is fully stocked for everything you need for your stay, along with in-unit laundry! Our home is: ❤ In front of Met Park and Playground ❤ 2 min walk to Whole Foods ❤ 4 min walk to Metro ❤ 5 min from Reagan National Airport (DCA) ❤ 6 min to Museums/Mall

Top guest favourite
Farm stay in Bluemont
5.0 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.

Guest favourite
The private backyard features a stock tank pool surrounded by wooden benches with cushions, styled with colorful flowers and greenery. String lights create a warm ambiance, illuminating the space for relaxation and outdoor gatherings.
Townhouse in Logan Circle
4.95 out of 5 average rating, 133 reviews

Historic Row Home Near Conv Center w/ Tank Pool

Historic Victorian row home featuring private backyard w/grill, firepit, and stock tank pool. Solar electricity, original hardwood floors and woodwork, renovated kitchen and bathrooms, and full laundry. Centrally located between Bloomingdale, Shaw & downtown, less than a mile to two Metro stations—NoMa-Gallaudet/NY Avenue (Red line) & Shaw/Howard (Green/Yellow lines)—and a mile to Amtrak at Union Station. Easy access to Convention Center, Capitol, Smithsonian, and the Mall. Happy dog fee $89

Guest favourite
A modern living room features two gray sofas with blue accent pillows, positioned around a light wooden coffee table. Natural light enters through the large windows, revealing a scenic view. A small plant adorns the table, while subtle greenery decorates the corners.
Flat in Reston
4.83 out of 5 average rating, 102 reviews

King Size Bed w/ Home Office

Welcome to Reston! This brand-new apartment boasts a grocery store on site (Wegmans), 10 minute walk to Reston Metro Station and modern luxuries for you to enjoy. The state-of-the-art kitchen has cookware, bakeware, flatware, and everything you need to kick off your culinary creations. The 4K Roku smart TV is waiting for you to catch up on all your shows. Laundry in unit for your convenience. Wifi, utilities, and linens are all included with your stay. We look forward to hosting you!

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 Station
4.9 out of 5 average rating, 110 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

Superhost
A two-story condo building is set against a twilight sky, with blooming trees framing the entrance. Pathways lined with greenery lead to the front, showcasing a well-maintained exterior and inviting balcony spaces on the upper floor.
Apartment in Annandale
4.83 out of 5 average rating, 169 reviews

Remodeled 1BR/1BA Condo: close to DC with pool!

Spacious and completely remodeled condo at Fairfax Heritage. Newly painted and featuring brand new carpet and vinyl flooring throughout the unit. All-new kitchen including stainless steel appliances, cabinets, quartz countertops, sink, lighting and plumbing fixtures. Remodeled bath. Generously-sized bedroom with double closet. Large private balcony overlooking treed courtyard. Common laundry on lower level, private storage unit. Grilling available in picnic area.

Guest favourite
Home in Waldorf
4.86 out of 5 average rating, 117 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, 144 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.
Guest house in Stevensville
4.99 out of 5 average rating, 361 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.

Guest favourite
A modern living area features a large rug with soft textures, complemented by a coffee table in the center. A stylish entertainment unit holds a flat-screen TV, while a dining area with high chairs is visible in the background. Greenery adds a touch of vibrancy.
Flat in Clarendon - Courthouse
4.97 out of 5 average rating, 121 reviews

Sojourn |Courtland Towers | Great Views

A fully furnished 1 bedroom which includes breathtaking views of DC and oversized floor plans. This community is conveniently located in the Courthouse neighborhood, just one block from the Courthouse metro station and on the edge of the Clarendon neighborhood. Great restaurants, shopping and a weekly farmer's market are just a few of the amenities this neighborhood has to offer. We offer one-, two- and three-bedroom units as well as studio apartments.

Popular amenities for Chesapeake and Ohio Canal rentals with a pool