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
A modern kitchen features warm wooden cabinetry, a sleek black stove, and a variety of kitchen appliances. A rustic dining table sits in the foreground, adorned with a woven runner and a wooden tray holding fresh fruit. The space is complemented by decorative shelves and natural light.
Apartment in Upper Marlboro
4.94 out of 5 average rating, 159 reviews

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

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, 398 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
The living room features a combination of stylish blue velvet sofas, accented by colorful throw pillows. A circular coffee table rests on a plush area rug. Large windows allow natural light to fill the space, while a flat-screen TV is mounted on the wall.
Apartment in Arlington
4.91 out of 5 average rating, 136 reviews

Deluxe 2BR Highrise | Arlington | Gym, Pool

You'll love coming home and unwinding in the stylish, elegant, and thoughtfully designed, 2 bedroom apartment in downtown Arlington. Your perfect home away from home. The prime location of this apartment is unbeatable, with everything you need right at your doorstep. You'll be just steps away from some of the city's best restaurants, bars, entertainment venues, and parks. ★ 15 Min to Reagan National Airport ★ 10 Min to Pentagon Mall ★ 12 Min to Georgetown Waterfront ★ 15 Min to Lincoln Memorial

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
5 out of 5 average rating, 156 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star 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 additional).

Guest favorite
A light-filled living area features a comfortable sectional sofa adorned with neutral tones and decorative cushions. The circular area rug in soft blue anchors the space, complemented by abstract art pieces on the wall and a modern mirror reflecting natural light.
Condo in Centreville
4.92 out of 5 average rating, 120 reviews

Peaceful patio condo

Stylish 1 bedroom condo on ground level with 1 designated parking space directly in front. This home provides a perfect setting for both luxurious and comfortable living. Bright southern exposure, No steps from parking, 2 smart TV, high speed internet, queen size bed, the patio opens to private green nature. Plenty of guest parking as well. Long paved walking trail passing by, Walk to Giant, Starbucks, and Restaurants. Less than 2 miles from Spa World. And 10 min drive to King Spa.

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, 311 reviews

Waterfront Getaway - 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
The living room features a comfortable U-shaped sectional sofa, arranged on a plush area rug. Light enters through a large window, and neutral artwork adorns the wall. A small table rests beside the sofa, enhancing the inviting atmosphere.
Apartment in McLean
4.95 out of 5 average rating, 111 reviews

Amenity Surplus, Free Parking, 20 min to DC, Gym

◆ ENTIRE UNIT - Perfect for business professionals, solo travelers, or families seeking a relaxing, quiet place to unwind ◆ UNBEATABLE LOCATION with Bus Stop right out front - Tysons Corner Mall: 3 mi, Washington DC: 10 mi, Metro Station 3 mi. ◆ FULLY STOCKED to make your stay the most convenient possible - includes in-unit washer & dryer ◆ SECURE BUILDING - requires key fob to access. ◆ FREE PARKING - 1 space.

Guest favorite
A modern living area features a light-colored sofa positioned next to a minimalist coffee table. The space includes two accent chairs and a dining table with matching chairs. Soft lighting is provided by a floor lamp, complemented by natural light from nearby windows.
Apartment in Tysons
4.93 out of 5 average rating, 27 reviews

Cozy 1 Bed Apt in Tysons | King BD | Near DC

Welcome to our modern 1 BR apartment in the heart of McLean! This modern, fully-furnished apartment offers a perfect blend of comfort and convenience. Enjoy a luxury living area, fully-equipped kitchen, modern amenities, resort style rooftop pool and state-of-the art gym. Whether you're here for business travel or vacation, our home is designed to provide everything you need for a relaxing and memorable stay.

Guest favorite
A modern living area is furnished with a light-colored sofa, complemented by dark accent pillows. A wooden coffee table sits at the center on a textured area rug. Large windows allow natural light to fill the space, featuring a view of greenery outside.
Apartment in Washington
4.94 out of 5 average rating, 168 reviews

Upscale 1Bdrm Apt in Heart of DC

Welcome to our cozy and charming one bedroom, one bathroom apartment in the heart of downtown Washington, DC! You’ll feel right at home in this beautiful space with tons of natural light, 60” 4k TV, a king sized Nectar mattress, and a fully equipped kitchen. Located just steps away from the city's most iconic landmarks, restaurants, and nightlife, our apartment is the perfect home base for your DC adventure!

Top guest favorite
An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.
Guesthouse in Annapolis
4.99 out of 5 average rating, 188 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.

Guest favorite
The living area features a flat-screen TV mounted on a white media console. A wooden coffee table occupies the center, surrounded by a textured area rug. A sunroom filled with natural light showcases a desk and panoramic views of the greenery beyond.
Condo in McLean
4.97 out of 5 average rating, 161 reviews

Luxury 1bd in Heart of Tysons

Located in the heart of Tysons close to shopping, restaurants, and 20 minutes from DC. Luxury 1bed/1bath with an incredible high rise view. Work in the sunroom with expansive views of DC. Everything you need for a relaxing vacation or productive work trip. Includes your own dedicated parking spot underground. Enjoy the multi amenity building by using the gym or the rooftop with a pool.

Guest favorite
A spacious master suite features a king-size bed with a decorative canopy, flanked by nightstands. Two armchairs provide seating, and a woven area rug adds warmth. A mural depicting nature adorns the wall, while large windows allow natural light. An accessible doorway leads to the bathroom.
Farm stay in Cockeysville
4.93 out of 5 average rating, 102 reviews

Historic Gatehouse Master Suite

Discover the historic charm of Maryland's scenic horse country! Our Master Suite, part of a Tudor-style gatehouse on an elegant estate, offers luxury and convenience. Minutes from Hunt Valley and Baltimore, indulge in a Carrera marble bathroom, a private deck with sweeping views, a full-size tennis court, a refreshing pool, and more. Immerse yourself in elegance and history.

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