Holiday rentals with a pool in White Plains

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in White Plains

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

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Top Guest favourite

Guesthouse in Southbury

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favourite

Home in West Milford

4.98 out of 5 average rating, 150 reviews

On The Rocks In The Hot Tub

Unique home featuring a large deck with an enclosed hot tub, indoor/outdoor bars, game room and seasonal pool (pool is not heated) Fall-Winter:Minutes away from the town of Warwick. Pennings, Heaven Hill Farm for apple-pumpkin picking, Peter Mountain, Mountain Creek for skiing. Many vineyards/cideries Summer: Boating on Greenwood Lake, kayak rentals, hiking (Appalachian Trail), drive-in theater, family activities at Wawanique State Park, Crystal Springs Golf and ice cream at Bellvale Creamery

Guest favourite

Home in Bethlehem

5 out of 5 average rating, 45 reviews

Lakeview Expanse

This is a renovated house situated on 14 acres in Litchfield County, CT. This is a 5 bedroom estate - 1 king size bed, 3 queen beds, 1 bedroom is a dedicated office with a queen size air mattress. 8 guests maximum. Heated saltwater pool (closed until May 2025), 5 seater/1 lounger hot tub, 2 outdoor dining area (one on deck, other on pool patio), 8 seater dining table, 4 seater breakfast table in kitchen, extra large jacuzzi in primary bathroom, wood burning fireplace. Completely private.

Superhost

Home in Litchfield

4.9 out of 5 average rating, 49 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

20% off JULY/AUG MONTHLY- Leave your worries at the front door of this New England gateway. An open, airy interior may make you feel like staying at home reading all day long, but there's so much to explore nearby. Head out to Black Rock State Park for a scenic hike through lush forests, followed by a leisurely afternoon sampling wines at local vineyards. Gather at this stylish home by the firepit w/loved ones. Pool deck area in rear of house is closed, under maintenance work until 5/26/25

Top Guest favourite

Home in Mendham Township

4.98 out of 5 average rating, 40 reviews

Historic Cottage with Private Pond & Pool

Step back in time to 1760 with the old world charm of Colonial America. Pre-dating our country by over a decade, our beautifully renovated 260+ year old home sits on 5 acres with a detached studio and 2 separate water features. Experience the private pond teeming with koi, frogs, and other wildlife or take a dip in the refreshing pool just steps away. Whether you seek a relaxing getaway or a portal back to the days of our founding fathers, our historic home promises the ideal retreat.

Guest favourite

Home in Hopatcong

4.94 out of 5 average rating, 49 reviews

3Acre LakeParadise SwimmingPool & Jacuzzi HotTub!

Lake front Estate with great views, stone walls, a stream & backwoods forest. The house has a brand new entertainment deck with a gazebo, grill & outdoor kitchen, a 12 x 18ft swimming pool and an enclosed gazebo with a HotTub for 7 . By the lake a 2nd deck with lounge chairs, umbrellas a 2nd grill, picnic area as well as a boat dock! Lake swimming area , adult and kids kayaks and life jackets! At the end of a small road, which makes it a secluded Paradise only 50 miles from NYC!

Top Guest favourite

Condo in Vernon Township

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Top Guest favourite

Apartment in Highlands

5 out of 5 average rating, 44 reviews

Highlands Hillside Hideaway w/Pool. beach, ferry

The guest apartment is located on the lower level of the main house on a beautiful, quaint hillside street. The 600 sq. ft. apartment is remodeled to provide a relaxed, beach getaway ambiance so you could enjoy a care free getaway. After waking from a restful slumber in the king-size bed, enjoy a beautiful oceanside morning walk to get your coffee at the local bakery or the local coffee shop. After you’ve grabbed your coffee, explore all that highlands has to offer.

Guest favourite

Apartment in Deer Park

4.88 out of 5 average rating, 17 reviews

Serene one bedroom retreat w/ backyard oasis

**Welcome to Your Private Oasis!** Enjoy a serene escape at our cozy one-bedroom retreat. Highlights include: - **Above-Ground Pool**: Perfect for refreshing dips. - **Outdoor Patio with Gazebo**: Ideal for relaxing and unwinding. - **Private Daybed**: Your perfect spot for lounging in peace. Experience the tranquility and privacy of our oasis while being close to local attractions. Book your stay today for a relaxing getaway! Pool is seasonal until October 1st.

Guest favourite

Apartment in Suffern

4.94 out of 5 average rating, 128 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

Guest favourite

Home in New Milford

4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

THIS IS A PRIVATE HOME🏡 THE BOTTOM FLR 2 car garage and a double bedroom with a full bathroom attached. THE MIDDLE FLR KITCHEN, LIVING, DINING 1/2 bath, wrap-around decks w/ a fire pit THE TOP FLR 1 K rm w/ a fireplace & a private deck 1 Q rm 1 ba w/ jet tub & standing shower 6 acres Foothills of the Berkshires May-Sept We provide day passes for access to tennis, pickle ball, pool, yoga, swim, water aerobics

Guest favourite

Home in Litchfield

4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

Nestled just outside the center of Bantam, this immaculate 3 bedroom 2.5 bath home with a pool is the ultimate retreat. The home is perfectly located for enjoying the area's top attractions, like lake activities, skiing at Mohawk, hiking the trails of White Memorial, Litchfield's Village Green where you can enjoy fine dinning, shopping and visit historic sites. Pool is open and heated May 15th to Sept 15th.