Holiday rentals with a pool in Chester County

Find and book unique homes with a pool on Airbnb

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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Guest favourite

Home in Parkesburg

4.93 out of 5 average rating, 27 reviews

Home near Parkesburg, Pool, 3 BR

Relax with the whole family at this peaceful place to stay. Guests will enjoy a spacious home with a pool and Fenced in backyard. (Pool open May 15th to Sept 15) The home is on a quiet street but still within a few minutes drive to area Restaurants, Walmart, grocery stores. Only an hours drive to Philadelphia, within 30 minutes drive to Lancaster, Strasburg, and Amish Attractions. The home has 3 bedrooms (1 king bed, 2 Queens) and a pullout sofa to sleep a total of 7 guests. Smart TV and WIFI.

Guest favourite

Guest suite in Oxford

4.92 out of 5 average rating, 97 reviews

Private, pet allowed quiet country oasis stay

Relax and enjoy the peaceful surroundings on one acre and nestled at the end of a cul-de-sac, with a farm and treeline view. Pet allowed and good to accommodate a short visit. Private space, parking and 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. Need a restaurant suggestion? Check the "Guidebook"

Guest favourite

Rental unit in Chadds Ford

4.92 out of 5 average rating, 228 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”. Always Amazing! Ask about guest passes avail with 2+ night stays. Winterthur, Brandywine River Museum, Wineries & more 3 Bedrms, 4 beds Beautiful large bathrm Dining/TV rm Kitchenette: Convection oven, Microwave, Keurig coffee maker, Electric fry pan WiFi, 55” HDTV Full size washer, dryer, refrig Gentle Pets welcome! **No Smoking, No Parties

Guest favourite

Cottage in Downingtown

4.97 out of 5 average rating, 197 reviews

The Cottage at Hoffman Barn

The Cottage at Hoffman Barn is a freestanding modern studio cottage located on what was once a dairy farm. The cottage is filled with eclectic art and modern appliances. Outside, your private deck is surrounded by mature specimen trees, birds and nature! You will love the charming waterfall patio and freedom to walk most of the four acre property including visits to goats and chickens at the stable. Most amenities needed for a lovely private getaway or a productive business trip are included.

Guest favourite

Guesthouse in Chester Springs

4.96 out of 5 average rating, 243 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.

Guest favourite

Guest suite in West Chester

5 out of 5 average rating, 181 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 favourite

Villa in Morgantown

5 out of 5 average rating, 96 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.

Guest favourite

Guest suite in Mohnton

4.99 out of 5 average rating, 109 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 favourite

Home in Honey Brook

4.94 out of 5 average rating, 247 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 favourite

Home in Nether Providence Township

4.94 out of 5 average rating, 113 reviews

Historic 1835 Farmhouse & Pool near Philadelphia

Price-Furness House: Historic 1830s Farmhouse in the Countryside outside Philadelphia. Birthplace to Will Price (Arts & Crafts Founder) and updated by Frank Furness (architect for some of Univ. of Penn) in 1880s, Modernised, 3,500 Sq. Feet, with 6 Bedrooms, Chef's Kitchen, Luxury Pool, Old-fashioned Wrap-Around Porch, 3 Dining Patios, Private Gardens incl. Orchard - 25m train ride to city. Perfect for visiting UPenn, Haverford, Swarthmore, Temple, Bryn Mawr, Villanova colleges.

Guest favourite

Home in Downingtown

4.94 out of 5 average rating, 115 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.

Guest favourite

Serviced apartment in Chadds Ford

4.99 out of 5 average rating, 112 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.