Vacation 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 favorite
Apartment in Bluemont
4.95 out of 5 average rating, 324 reviews

A Great Getaway — Foxglove Retreat

Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

Top guest favorite
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, 414 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 favorite
A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.
Farm stay in Purcellville
4.98 out of 5 average rating, 222 reviews

The Hunt Box @ Tally Yo Farm

Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee

Top guest favorite
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 Saint Michaels
4.97 out of 5 average rating, 189 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 favorite
A spacious living area is showcased, featuring a soft rug and modern furniture. The room includes a gray sofa, a round coffee table, and a dining space with four chairs. The walls are painted a deep blue, highlighting a decorative wall art piece.
Apartment in Arlington
4.92 out of 5 average rating, 174 reviews

Sojourn | Courtland Towers | 2 BR

A fully furnished 2 bedroom 2 bath. This home comes outfitted with one King and two twin beds. We are happy to set up the two twin beds as one bed with a full 2 days notice. 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

Top guest favorite
An expansive outdoor pool is set against a backdrop of lush greenery and trees. Warm lighting from the stone cottage bathes the area in a soft glow, creating a tranquil ambiance in the early evening. The pool's water reflects blue hues, inviting a sense of relaxation.
Cottage in Wrightsville
4.96 out of 5 average rating, 188 reviews

-The Pool Cottage at The Roundtop Estate-

Experience the ultimate private, romantic retreat tucked away from the hustle and bustle. Our unique hideaway offers over a mile of seclusion from the nearest road, immersing you in nature’s quiet beauty. Relax in the Brand-new Saltwater pool and hear the gentle hums of a train rolling along on the other side of the river. Indulge in the luxurious amenities our property has to offer. Rejuvenate in the hot tub, or warm up by the Breeo Firepit with a Latte from the Breville Espresso Machine.

Top guest favorite
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, 609 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 of an Acre with access to wooded a trail featuring 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 favorite
Guest suite in Annapolis
4.94 out of 5 average rating, 127 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 private 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 deadbolt; no shared indoor spaces; separate entrances).

Top guest favorite
A cozy living area features a spacious sectional couch adorned with patterned cushions. A wooden coffee table sits centrally, with a decorative rug beneath. A brick fireplace is present, flanked by windows allowing natural light, and a green door leads to the exterior.
Guesthouse in Cambridge
4.99 out of 5 average rating, 135 reviews

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Top guest favorite
An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.
Home in Robertson
4.93 out of 5 average rating, 241 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Top guest favorite
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, 337 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.

Top guest favorite
The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.
Home in Lusby
4.99 out of 5 average rating, 165 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

Popular amenities for Chesapeake and Ohio Canal rentals with a pool

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