Vacation 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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Guest favorite

Guest suite in Upper Marlboro

4.99 out of 5 average rating, 107 reviews

Basement Suite in Golf-course Community (DC metro)

A beautiful home in the Beech Tree Lake Presidential Golf Course community. Our cozy, spacious, new, private, basement suite is welcoming you. You can enjoy golfing on beautiful green rolling hills, Luxury Golf Course Clubhouse, restaurant & bar, walking trails around the Lake Presidential and morning coffee on the patio. Easy access to Washington, DC, Annapolis, AFB, Chesapeake Bay, Redskin FedEx Field and Baysox Baseball Stadiums, Six Flags Amusement Park, Show Place Arena & Equestrian Center.

Guest favorite

Cottage in Hamilton

4.95 out of 5 average rating, 338 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 favorite

Condo in McLean

4.83 out of 5 average rating, 137 reviews

3Bedrooms/2Baths Totally Comfortable & Convenient!

Enjoy easy access to everything from this conveniently located 3 bedroom condo with balcony and pool. Off all major routes 495/66/7/267. Centrally located between 2 airports: DCA Reagan & IAD Dulles w/ direct access to Dulles Express, 2 metro stops. Walk to Tysons mall via a new pedestrian bridge. Close to retail, offices, restaurants, theatre, bowling; Outdoor venues like Wolftrap, Perch, Shipgarten, Beirgarten, CirqueduSoleil; Shopping, parks, dining, entertainment, library, markets & more.

Guest favorite

Guest suite in Woodbridge

4.89 out of 5 average rating, 258 reviews

Newly renovated private guest's suite with parking

Completely remodeled lower level guest suite, accommodates up to 4 guests. Features a private entrance and parking on premises for 1 car. Walk or bike to Veterans Park and Occoquan Bay National Wildlife Refuge. Conveniently located 12 minutes away from Quantico Marine Corp Base and Historic Occoquan attractions & restaurants. 30 minutes from Washigton DC, Old Town Alexandria and National Harbor, MD. Come enjoy this bright and quiet private stay. *Please note this is a NO SMOKING environment. *

Guest favorite

Guesthouse in Monrovia

4.96 out of 5 average rating, 141 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

Guest favorite

Cabin in Culpeper

4.97 out of 5 average rating, 173 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Guest favorite

Home in Fairfax

4.96 out of 5 average rating, 160 reviews

6BR Modern Home w/HEATED Pool & Screened in Porch

Pool/Hot Tub open all year round! Beautiful modern house only 5 minutes from 495 and 20 minutes to Washington DC. New saltwater HEATED Pool with hot tub and tanning ledge. Fantastic Tec heat mirror glass grill in the screened-in porch with commercial-grade vents to clear the smoke. Shopping center with Trader Joe's and Total Wine 2 minutes away. Perfect family home for reunions or vacations. This is not a party or events house. We require guests to have positive reviews to book.

Guest favorite

Cottage in Saint Michaels

4.97 out of 5 average rating, 155 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Superhost

Condo in Annandale

4.83 out of 5 average rating, 109 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 favorite

Guesthouse in Highland

4.98 out of 5 average rating, 274 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

Guest favorite

Guesthouse in Haymarket

4.98 out of 5 average rating, 120 reviews

Private Basement Bungalow Getaway

Private entrance to a large basement with a private bedroom (with TV), bathroom and living room. Conveniently located off of 66 at the intersection of the Blue Ridge Mountains and the historic battlefields of Bull Run. A perfect couples getaway in the middle of Virginia wine country with pool, fire pit and morning walks in the Rural Crescent. Come join us for an adventure! -Jiffy Lube Live 7mile distance -Multiple wineries & breweries -Within 50mins of DC

Guest favorite

Home in Fort Washington

4.93 out of 5 average rating, 121 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

Enjoy the comfort of this fully remodeled, beautifully decorated single family home. This home is located within minutes of National Harbor Waterfront, MGM, Tanger outlets, many restaurants and shops, and only 20 minutes from Washington DC and 20 minutes away from DCA - Ronald Reagan Washington National Airport. The home is built on half an acre of land, with a brand new in-ground pool in the backyard for enjoyment in the summer months.