Vacation rentals with a pool in Delaware County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Delaware County

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

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Guest favourite

Apartment in Chadds Ford

4.93 out of 5 average rating, 201 reviews

Spacious & Peaceful, Pvt Pool-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

Sep. 5 – 12

$426 CAD per night

Guest favourite

Apartment in Media

4.98 out of 5 average rating, 52 reviews

La Kaye Fle'(The Flower House) Exec Ste with Pool

Once you've arrived on the grounds of La Kaye Fle' consider you're home! Whether you're here for work or play or both if you please, this 1st level, 900 sq ft suite is perfect for your travels. There are no worries! We are located in the borough of Media, such a rare find! Private apartment, off street free parking, talk of the town grounds and fine amenities. There is a saltwater heated pool open in the warmer mos , private deck, walking distance to restaurants, bars, shopping and public trans.

Feb. 27 – Mar. 6

$361 CAD per night

Guest favourite

Guesthouse in Chester Springs

4.96 out of 5 average rating, 226 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.

Nov. 19 – 26

$241 CAD per night

Superhost

Guest suite in Folcroft

5.0 out of 5 average rating, 20 reviews

Creekside Private Lower Level Apartment

Be the first to enjoy a newly renovated full kitchen and bathroom. Located close to the PHL airport and 15 minutes from Downtown. Zero traffic and fox and deer sightings in the backyard. There really is no street like ours nearby. This is a great place to work from. Apartment is completely private with a nice (motion detected) lighted brick and concrete path to entrance around back. You will be on the lower level so you will occasionally hear the pitter patter of owner's footsteps upstairs.

Sep. 14 – 21

$172 CAD per night

Guest favourite

Guest suite in West Chester

5.0 out of 5 average rating, 161 reviews

Tranquil, Picturesque - 4 miles to LongwoodGardens

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. Both grand & relaxing, you will be staying in the 1500 sq. ft. gorgeous private walk-out lower level with 2 bedrooms, wine cellar dining, pool table & 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, historical sites, bars & wineries.

Sep. 19 – 26

$376 CAD per night

Guest favourite

Guesthouse in Elk Mills

4.98 out of 5 average rating, 42 reviews

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

Oct. 22 – 29

$186 CAD per night

Guest favourite

Apartment in Flourtown

4.98 out of 5 average rating, 206 reviews

Apartment attached to private home

This two bedroom apartment is attached to a private home in a suburban neighborhood. One bedroom has twin beds, another a queen & a twin sofa bed. Living room has a queen sofa bed. The apartment sleeps 7. Full kitchen. No steps involved. Walk-in shower. 36” doorways. Hallway railings. Small dog friendly. We request 24 hr notice & arrival before 8:00pm. We do not offer Airbnb from 7/4 weekend through Labor Day weekend. No smoking or vaping indoors or on the property.

Sep. 18 – 25

$154 CAD per night

Guest favourite

Home in Downingtown

4.94 out of 5 average rating, 103 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.

Nov. 14 – 21

$255 CAD per night

Guest favourite

Apartment in Chadds Ford

4.98 out of 5 average rating, 59 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.

Nov. 8 – 15

$169 CAD per night

Guest favourite

Guest suite in Eagleville

4.83 out of 5 average rating, 261 reviews

The Vintage Suite at Park House

Welcome to the Vintage Suite at Park House! The cozy, vintage themed suite features a private entrance and balcony overlooking over two acres of the park-like property. Dedicated parking that can be seen from the suite. The shared pool and hot tub are available from Memorial Day to at least Labor Day (all depends on when the fall leaves come). Please, no parties!

Oct. 29 – Nov. 5

$172 CAD per night

Guest favourite

Barn in West Chester

5.0 out of 5 average rating, 15 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.

Oct. 24 – 31

$233 CAD per night

Guest favourite

Guest suite in West Chester

4.99 out of 5 average rating, 203 reviews

Your own peaceful, natural retreat!

So much better than staying in a hotel! A completely private apartment! Quiet... comfortable... accessible. A perfect place for business travelers, your holiday guests, nature lovers, history buffs or anyone just wanting to escape the hustle bustle for a few days. Only 3 minutes away from downtown West Chester.

Sep. 6 – 13

$179 CAD per night