
Holiday 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.

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

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.

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.

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, Keurig 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.

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.

Wilde Haven - Waterfront A-Frame Studio - Site 141
Relax in this cozy waterfront A-frame studio at Red Run Resort & Campground. Features include a king-size bed, spa-style bathroom with a soaking tub AND separate shower, and your own deck with stunning water views. Grill dinner over your own firepit with a built-in grate or cook indoors with a 2-burner cooktop in the kitchenette. Whether you're unwinding by the fire, soaking in the tub, or taking in the waterfront views, this peaceful retreat is perfect for a relaxing classic A-Frame escape.

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!

Cozy country stay getaway that's 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.

Peaceful Retreat Pool and great outdoor space
Peaceful and spacious home on a 2 acre lot with a small above ground pool. Great outdoor space with fire pit and seating area. Located just minutes from beautiful Lancaster County. 15 to 30 minutes from most local attractions. Philadelphia is about an hour away. There is an Amish farm market nearby. Our place is great for families with children, couples, business travelers and more. *Please read the entire listing before you decide to book and message me with any questions you may have.

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.

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.

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.
Popular amenities for Chester County rentals with a pool
House rentals with a pool

Quiet Country Home in Parkesburg, In Ground Pool

Whitehorse view of Amish country

Cozy 4BR Parkesburg Home with Pool & Sunroom

Spend Fall Days in Nature Wedding Season

Family home with Pool, Hot-tub & Pickleball court!

Modern Farmhouse: Pool, Hot Tub & Pickleball

Comfort, Fun, & charming! - 5BR oasis w/ Pool

Happy Trails Guest House “private pool & hot tub”
Other holiday rentals with a pool

Sonoma Tiny Home at Red Run - Site 104

A-Frame Studio w/ Ramp Entry at Red Run - Site 136

Creekfront Glamping Pod - Site 42

Waterfront A-Frame Studio at Red Run - Site 138

Waterfront A-Frame Studio at Red Run - Site 137

Waterfront A-Frame Tiny Home at Red Run - Site 116

Waterfront A-Frame Studio at Red Run - Site 139

Reflections Retreat Cascade Tiny Home - Site 119
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- Pennsylvania Convention Center
- Hersheypark
- Lincoln Financial Field
- Citizens Bank Park
- Dorney Park & Wildwater Kingdom
- Longwood Gardens
- Fairmount Park
- Betterton Beach
- Penn's Landing
- Philadelphia Museum of Art
- Diggerland
- 30th Street Station
- French Creek State Park
- Marsh Creek State Park
- Philadelphia Zoo
- Aronimink Golf Club
- The Franklin Institute
- Wells Fargo Center
- Wissahickon Valley Park
- Crystal Beach Manor, Earleville, MD
- Valley Forge National Historical Park
- Independence Hall
- Franklin Square
- Hershey's Chocolate World