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Vacation rentals with a pool in The Berkshires

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in The Berkshires

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

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Cabin in Stephentown

4.84 out of 5 average rating, 238 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Jun 2 – 9

ﺩ.ﺇ929 per night

Bungalow in Easthampton

4.92 out of 5 average rating, 433 reviews

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Jul 23 – 30

ﺩ.ﺇ602 per night

Home in Ghent

4.87 out of 5 average rating, 270 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from of Hudson. Cozy up in front of the wood burning stove as you take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

Dec 17 – 24

ﺩ.ﺇ790 per night

Farm stay in Red Hook

4.99 out of 5 average rating, 126 reviews

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Just named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' Rumaan Alam First Floor open space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer/Dryer, Fridge/Freezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Gas Fireplace & Cable TV Second Floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

Mar 20 – 27

ﺩ.ﺇ2,278 per night

Apartment in Kent

4.93 out of 5 average rating, 127 reviews

Loft 22

Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*

Apr 15 – 22

ﺩ.ﺇ551 per night

Home in Woodstock

4.98 out of 5 average rating, 101 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Sep 6 – 13

ﺩ.ﺇ2,987 per night

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

Aug 29 – Sep 5

ﺩ.ﺇ802 per night

Apartment in Brookfield

4.94 out of 5 average rating, 186 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Mar 16 – 23

ﺩ.ﺇ431 per night

Guesthouse in Lenox

4.95 out of 5 average rating, 284 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 5 – 12

ﺩ.ﺇ533 per night

Tiny home in Ghent

4.96 out of 5 average rating, 139 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

New Tiny House living space on 30 private acres with a mile of walkable trails in Beautiful Columbia County near Hudson/Chatham/Kinderhook. House has everything you need with a Queen bed, full bed, and full kitchen. The cozy space is an ideal getaway for relaxing. In the warm months enjoy the large in ground pool and renovated barn pool house. Enjoy the 6 person Sauna year round. ** Pool closed Mid-October - Mid-May, Confirm before booking.

Jul 9 – 16

ﺩ.ﺇ868 per night

Cabin in Red Hook

4.96 out of 5 average rating, 305 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Aug 22 – 29

ﺩ.ﺇ1,709 per night

Apartment in Enfield

4.99 out of 5 average rating, 144 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

Oct 22 – 29

ﺩ.ﺇ379 per night

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for The Berkshires rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in New Paltz

4.98 out of 5 average rating, 437 reviews

midcentury modern in ground pool walk 2 trail/town

Jul 14 – 21

ﺩ.ﺇ3,361 per night

Home in Gloversville

4.97 out of 5 average rating, 315 reviews

Indoor Heated Pool in the Adirondacks

Apr 23 – 30

ﺩ.ﺇ822 per night

Home in Hudson

4.93 out of 5 average rating, 227 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

Sep 13 – 20

ﺩ.ﺇ2,112 per night

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Dec 26 – Jan 2

ﺩ.ﺇ2,944 per night

Home in Saugerties

5.0 out of 5 average rating, 132 reviews

Upstate Modern Scandinavian Barn in the Catskills

Nov 6 – 13

ﺩ.ﺇ2,524 per night

Home in Cheshire

5.0 out of 5 average rating, 118 reviews

Pool House

Apr 15 – 22

ﺩ.ﺇ530 per night

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Dec 14 – 21

ﺩ.ﺇ2,027 per night

Home in Saugerties

4.96 out of 5 average rating, 150 reviews

Lux 1800's renovated farmhouse w/hot tub+pool

Oct 21 – 28

ﺩ.ﺇ4,185 per night

Condo rentals with a pool

Condo in Windham

4.89 out of 5 average rating, 133 reviews

Cozy Mountain hideaway Windham, Hunter

Aug 21 – 28

ﺩ.ﺇ340 per night

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Apr 7 – 14

ﺩ.ﺇ592 per night

Condo in Vernon Township

4.97 out of 5 average rating, 217 reviews

Rustic Chic at Mountain Creek! Pool|Hot Tub|Sauna

Dec 1 – 8

ﺩ.ﺇ530 per night

Condo in Norwich

4.99 out of 5 average rating, 112 reviews

Peaceful Oasis steps from Mohegan Sun

Oct 6 – 13

ﺩ.ﺇ546 per night

Condo in Vernon Township

4.97 out of 5 average rating, 144 reviews

Comfy Studio at Mountain Creek Resort

Jan 15 – 22

ﺩ.ﺇ381 per night

Condo in Vernon Township

4.95 out of 5 average rating, 238 reviews

NYC Escape 1 hr away

Aug 13 – 18

ﺩ.ﺇ659 per night

Condo in Norwich

4.99 out of 5 average rating, 101 reviews

Jacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan

Dec 12 – 19

ﺩ.ﺇ786 per night

Condo in Vernon Township

4.95 out of 5 average rating, 729 reviews

Appalachian Lodge Top Floor w/views

Sep 25 – Oct 2

ﺩ.ﺇ613 per night

Home rentals with a private pool

Home in Lagrangeville

4.84 out of 5 average rating, 120 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Sep 27 – Oct 4

ﺩ.ﺇ2,258 per night

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Sep 17 – 24

ﺩ.ﺇ2,299 per night

Farm stay in Fleischmanns

4.91 out of 5 average rating, 11 reviews

Escape to a Dreamy 1857 Farmhouse in Fleischmanns

Jan 23 – 30

ﺩ.ﺇ1,504 per night

Villa in Coxsackie

4.99 out of 5 average rating, 80 reviews

Magnificent Hudson River Estate with Infinity Pool and Spa

Apr 18 – 25

ﺩ.ﺇ4,217 per night

Home in Woodstock

4.6 out of 5 average rating, 10 reviews

Luxury Retreat in the Catskills

Aug 31 – Sep 7

ﺩ.ﺇ4,185 per night

Home in Lanesville

4.77 out of 5 average rating, 205 reviews

Go Hiking and Skiing from a Family-Friendly Farmhouse

Mar 13 – 20

ﺩ.ﺇ1,564 per night

Home in Rhinebeck

5.0 out of 5 average rating, 65 reviews

Rhinebeck Country Living with a Modern Twist

Oct 2 – 9

ﺩ.ﺇ2,320 per night

Destinations to explore