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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Guest favorite

Cottage in Hamilton

4.94 out of 5 average rating, 309 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!

Sep 17 – 24

G$55,112 GYD per night

Guest favorite

Condo in McLean

4.82 out of 5 average rating, 126 reviews

3 Bedroom/King-Master/Free-Parking/POOL (Rare)

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.

Apr 2 – 9

G$56,688 GYD per night

Superhost

Guest suite in Oakton

4.79 out of 5 average rating, 106 reviews

N. Virginia convenience to DC and Old town Vienna

This is a finished lower level of a townhouse in a quiet Oakton, Virginia suburb of Washington DC. The private entrance side is above ground. The large French doors allow lots of light in. We are located half way between Regan National and Dulles airports with public transportation to both. The bus stop is 50 yards from the door and the bus trip is less than 2 miles to the Vienna/George Mason University Orange line metro station. You will have key to the private entrance and laundry room.

Aug 31 – Sep 7

G$16,819 GYD per night

Guest favorite

Home in Harpers Ferry

4.97 out of 5 average rating, 156 reviews

Harpers Ferry Farmhouse, Heated Year Round Pool

Located on the Blue Ridge Mountains of West Virginia, this 1800s farmhouse plus bonus barn studio apartment have been renovated with every modern comfort. The incredible saltwater plunge pool is heated and can be used all year! Perfect for groups. Minutes from outdoor activities, wineries, breweries, and more that make Harpers Ferry, WV such a draw. 1 hour from Baltimore & DC, 3 hours from Philadelphia, 4 hours from NYC. Follow @perennialstays for more details and behind the scenes.

Apr 25 – May 2

G$177,296 GYD per night

Guest favorite

Guesthouse in Monrovia

4.95 out of 5 average rating, 110 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:)

Oct 11 – 18

G$44,921 GYD per night

Guest favorite

Guest suite in Catonsville

4.94 out of 5 average rating, 470 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Sep 2 – 9

G$20,261 GYD per night

Guest favorite

Home in Fairfax

4.96 out of 5 average rating, 145 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.

Dec 27 – Jan 3

G$234,918 GYD per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 137 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.

Sep 6 – 13

G$111,851 GYD per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 264 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.

Oct 18 – 25

G$24,973 GYD per night

Guest favorite

Home in Washington

5.0 out of 5 average rating, 9 reviews

Palisades Retreat

Lovely retreat in Palisades. Private one-bedroom walkout Basement Apartment in a large home with designated parking in the driveway and a separate private entrance from the main house. Includes a tempered swimming pool. Close to public transportation, Georgetown and George Washington Universities and Sibley and Georgetown University Hospital. Ideal for business travel, visiting friends and relatives in Washington and vacationers.

Jun 16 – 23

G$43,244 GYD per night

Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 106 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Sep 25 – Oct 2

G$80,979 GYD per night

Guest favorite

Home in Lusby

5.0 out of 5 average rating, 111 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Summer is a 1-week minimum, Friday-Friday* Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300 foot private beach. The year-round property has a pier, in-ground pool (May-October) with amazing river views.

Jun 27 – Jul 4

G$184,584 GYD per night