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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Top guest favorite
Apartment in Bluemont
4.95 out of 5 average rating, 325 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, 416 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 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

Top guest favorite
A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.
Apartment in Stevensville
4.98 out of 5 average rating, 304 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

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, 613 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

Guest favorite
A cozy sleeping area is presented with a spacious bed dressed in soft, light-colored bedding. Two bedside lamps provide warm illumination, complementing the neutral tones of the walls. A small side table and a wooden accent table are positioned beside the bed.
Guest suite in Oakton
4.82 out of 5 average rating, 151 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.

Guest favorite
A spacious pool area features a heated in-ground pool and spa surrounded by lounge chairs. A well-maintained lawn and shaded seating areas complement the outdoor space, while a house is visible in the background, nestled among the trees.
Home in Marshall
4.93 out of 5 average rating, 138 reviews

Clean 5BR w Heated Pool, Spa - Horse, Wine Country

Escape the city to this spacious 5BR / 3.5BA home with a heated pool and spa on 8 acres in the heart of Northern Virginia's Horse and Wine country. The house is professionally designed for large groups of adults and kids for family vacations, reunions, and retreats. 2 miles from the one-stop-light town of Marshall with nationally recognized restaurants, bakeries. And in the heart of Virginia's Horse & Wine country - 7 wineries, equestrian facilities/shows, and state park within 15 minutes.

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, 243 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, 341 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 favorite
A modern kitchen is equipped with stainless steel appliances and sleek cabinetry, complemented by a light-colored island. A dining table with chairs is positioned near floor-to-ceiling windows, allowing natural light to brighten the space.
Apartment in Arlington
4.93 out of 5 average rating, 112 reviews

Sojourn | VA Square | 2 BR

North Arlington VA Apartments come with the features you expect and want, and even some you’ve always dreamed of, at Virginia Square Towers. We have an eye for luxury, comfort, and practicality, and our amenities reflect that. Enjoy your private space in your furnished two bedroom without worrying about bothering your neighbors or being bothered with excessive sound when you have a home that’s built with noise-reducing walls and floor-to-ceiling windows.

Guest favorite
A modern kitchen is visible, featuring stainless steel appliances and sleek cabinetry. A cozy living area showcases a curved sofa set atop a plush red rug, with two round coffee tables. Light enters through windows, creating a bright and inviting space.
Apartment in Washington
4.79 out of 5 average rating, 475 reviews

#2 Foggy Bottom/Georgetown Apartment

Stay in a luxury apartment in one of DC’s most walkable neighborhoods, between the West End and Georgetown on Pennsylvania Ave. Walk to the National Mall, Smithsonian museums, historic Georgetown, top restaurants, and nightlife. Renovated in 2016, this stylish space offers modern comforts, plus free access to Balance Gym Foggy Bottom & Capitol Hill. Enjoy waterfront views, scenic parks, and DC’s vibrant culture—all just minutes away!

Top guest favorite
A spacious mountain home is set against a backdrop of trees, with a gently sloping field leading to a small pond in the foreground. A wooden fence encircles the property, highlighting the serene outdoor environment that encompasses the house.
Home in Sabillasville
4.95 out of 5 average rating, 146 reviews

Stoney Spring Overlook

This beautiful mountain home offers breathtaking views of the surrounding Catoctin Mountains. The area is rich with outdoor adventures and attractions. Though it feels like a peaceful retreat tucked away in the mountains, it’s only 30 minutes from Frederick, MD, historic Gettysburg, PA, and about an hour from the Washington, D.C. area. Whether you’re seeking a quiet escape or hoping to explore more of the Frederick County.

Popular amenities for Chesapeake and Ohio Canal rentals with a pool

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