Vacation rentals with a pool in Chester County

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Top-rated rentals with a pool in Chester County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene view captures the home nestled amidst green grass and trees. The pool glistens in the sunlight, surrounded by a spacious patio and seating area. Rolling farmland stretches across the horizon under a soft, cloudy sky.

Villa in Paradise

4.98 out of 5 average rating, 158 reviews

Hilltop Mansion: Farm Views+HotTub+Pool+GameRoom.

This gorgeous home is located at the very top of a hill in one of the most central locations in Lancaster County. You'll be surrounded by breathtaking views of the nearby farmland and the interior has been beautifully decorated in calming, neutral tones. No amenity has been spared for your stay some of which include a spacious master suite, stunning kitchen, Nespresso machine, large game room, a kid's toy room, a firepit, yard games and a patio with outdoor seating, a hot tub, pool and a grill.

Guest favorite

A cozy living area features a dark brown leather sectional sofa facing a 55” HDTV. A round table with fresh flowers is positioned near the sliding glass doors, which provide natural light and a view of the outdoor patio. Light-colored dining chairs are arranged around a wooden dining table.

Apartment in Chadds Ford

4.91 out of 5 average rating, 263 reviews

Spacious & Peaceful, Pvt, 3mi Longwood Gardens

Comfy & Spacious Private Downstairs Suite in 2 acres of nature Private Pool Heated end of May to Sept 3 mi to Longwood Gardens aka “America’s Versailles”. Amazing! Ask about guest passes to the Gardens w/2 night stays. Winterthur, Brandywine River Museum, Wineries & more 3 Bedrms, 4 beds Beautiful lg bathrm & Powder room Dining/TV rm Kitchen: Convection oven, Cooktop, Microwave, Keurig coffee maker WiFi, 55” HDTV Full size washer, dryer, refrigerator Gentle Pets welcome! *No Smoking, No Parties

Top guest favorite

A private swimming pool is surrounded by lush greenery, with colorful inflatable toys resting on the water's surface. Poolside lounge chairs are positioned on a gravel area, providing space for relaxation. Sunlight filters through the trees, creating a serene atmosphere.

Guesthouse in Chester Springs

4.96 out of 5 average rating, 262 reviews

Newly Renovated Chester Springs Guesthouse

The newly renovated one bedroom apartment (that can accommodate up to 5 guests) above the detached garage at Artisan Studios provides a lovely guesthouse retreat. Nestled in the woods in beautiful Chester County, you'll enjoy privacy and seclusion even though you're just a 5 minute drive to anything you could need. We're just 8 miles from the PA Turnpike and only 38 miles (45 minutes to an hour) from Philadelphia. Feel free to bring your pet, as long as they are house broken or litter trained.

Top guest favorite

The back view of the property reveals a charming home surrounded by lush greenery. A clear pool is positioned in the foreground, emphasizing the tranquil outdoor space. The expansive deck extends from the house, creating a welcoming area for relaxation among the trees.

Guest suite in West Chester

5 out of 5 average rating, 189 reviews

Spacious Studio Suite 4 miles to Longwood Gardens

As you come down the long private drive, you will be reminded that you are staying in one of most coveted areas of Chester County. Pictured is the main house which we reside in. Both grand & relaxing, you will be staying in the 1500 sq. ft. private walk-out open-concept studio with wine cellar bedroom, pool table, dedicated playroom & granite island. Sitting on 12.9 park-like acres every view is private with your own private pool. So tranquil yet just minutes away to Longwood Gardens and more.

Guest favorite

The outdoor patio area features a spacious pool surrounded by lounge chairs. An outdoor seating arrangement with a fire pit is positioned before the pool, inviting relaxation. The stone farmhouse and trees in the background complete the serene retreat atmosphere.

Villa in Morgantown

4.99 out of 5 average rating, 121 reviews

Mill Road Farmhouse: Restored with Beautiful Pool.

The Mill Road Farmhouse is a destination in and of itself. Immaculately restored inside and out, this home is a true retreat in the middle of Amish Country. We have a feeling you will be spending all of your time relaxing by pool and hot tub during the warmer months (or maybe grilling up a feast in the brand new outdoor kitchen area) and curled up next to one of the four indoor fireplaces during the winter months. And then of course end each day star-gazing while sitting around the campfire.

Top guest favorite

A two-story house is surrounded by lush greenery and colorful plants. The exterior features a mix of brick and siding, complemented by purple shutters. A set of stairs leads to the front door, while a shaded porch provides a welcoming entryway.

Home in Coatesville

4.97 out of 5 average rating, 111 reviews

King’s place, hot tub Pool is open!

New hot tub, above ground pool with deck built into it ! Recently remodeled, Centrally located on a 1 acre lot. Not far from all the tourist attractions that Lancaster has to offer. 1 hr from philly airport, 15 minutes from downingtown, 15 minutes from gap,and 20 minutes from Intercourse. A quiet neighborhood with a spacious back yard, which is great for kids. Whether you bring cornhole, use the grill, or sit around the propane fire pit. The yard and large back deck have so much to offer!

Guest favorite

An expansive inground pool is showcased, bordered by a white fence and offering a slide for recreation. Lounge chairs and dining tables with umbrellas create inviting spaces for relaxation. Scenic views of farmland and rolling hills are visible in the background, enhancing the outdoor experience.

Guest suite in Oxford

4.89 out of 5 average rating, 121 reviews

Cozy country stay - heated pool and pet allowed!

Large solar heated pool for summer fun! Relax and enjoy the peaceful surroundings on one acre at the end of a cul-de-sac. Pet allowed large property with room for everyone to stretch their legs. Private space all to yourself, with parking and seperate entrance. AC, queen bed, foldout couch, microwave, Keurig coffee, mini stove and mini fridge. There is a bathroom with necessary toiletries, sink and large walk in shower. Amish style sticky bun, fruit and juice will be provided for breakfast.

Top guest favorite

An outdoor area features a securely fenced pool surrounded by wooden decking. Lounge chairs and tables are arranged nearby, set against a backdrop of autumn foliage and tall trees. The grassy area is dotted with fallen leaves, providing a relaxed atmosphere.

Guest suite in Mohnton

4.99 out of 5 average rating, 136 reviews

Loft 311

Enjoy a peaceful vacation tucked away in a valley below a swath of Lancaster County farmland. Located in Adamstown, PA, "Antiques Capital USA", this studio-style loft is less than 5 minutes from 272, 222, and the PA Turnpike, and less than half an hour from the many tourist attractions and local hotspots in Lancaster and Reading. If you enjoy bicycle riding, you'll be able to travel on your own steam to a dozen local antique shops, or take it easy and lounge by the pool with the family.

Guest favorite

A modern living area is characterized by exposed wooden beams and a cozy fireplace. Two spacious sofas are positioned around a central coffee table, with natural light streaming in through large windows. Artwork adorns the walls, adding a touch of personality to the space.

Home in Honey Brook

4.93 out of 5 average rating, 271 reviews

Ode to the '70's - hot tub & pool in Honey Brook

4 bedroom/2 bath home - modern renovation with retro flair. Large backyard with saltwater pool, hot tub, grill, fire pit, and kids playhouse! (Pool open May-Sept) We've furnished this home with our favorite pieces to create a space that inspires creativity & life. Pickleball courts within walking distance in local park. Paddles and balls provided. Close to the Honey Brook Thrift Store, September Farms & other local attractions! 1/2 hour to Lancaster City, Exton/King of Prussia.

Guest favorite

A serene pool area features a clear blue swimming pool surrounded by a stone deck. Adjacent to the pool, a light blue guest house is visible, offering ample outdoor space and greenery. Trees dot the landscape, providing a peaceful backdrop.

Home in Downingtown

4.94 out of 5 average rating, 118 reviews

Lakefront Guesthouse

Come stay at our beautiful one bedroom guest house that sits on an eight acre lakefront property. This poolside guest house includes a spacious kitchen, full bathroom, and one bedroom with a queen sized bed. Whether you're local or visiting from out of town, spend your getaway relaxing by Marsh Creek Lake or take advantage of the wide variety of local attractions that Chester County has to offer. Our guest house is for a maximum of two adults only. No children.

Top guest favorite

An aerial view captures a spacious property featuring a large pool surrounded by a stone patio. The multi-level house displays varying architectural elements and an expansive deck area. Lush greenery complements the outdoor setting, providing a serene atmosphere for relaxation.

Apartment in Chadds Ford

4.99 out of 5 average rating, 180 reviews

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Guest favorite

A spacious room features a large bed with soft linens, flanked by bedside lamps. A cozy red seating area with a small ottoman is present, alongside a wooden table and chairs. Natural light floods the space, complemented by a stylish wall clock and artwork decorations.

Barn in West Chester

4.95 out of 5 average rating, 41 reviews

Private Barn Retreat With Pool 1BR | 1BA | Parking

Cozy top floor barn with central air & heat. Here you'll find a private & secluded bedroom and bathroom fit for 2. A small "kitchenette" is available as well as an outdoor pool area to use at your leisure. Convenient location, 10 minutes from the center of West Chester & Downingtown. Easy parking directly outside of the barn. Our space is best suited for short term stays, so we limit bookings to one week.