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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

R4,753 ZAR per night

Bungalow in Easthampton

4.92 out of 5 average rating, 431 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 21 – 28

R3,218 ZAR 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.

Mar 18 – 25

R4,354 ZAR 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.*

Sep 16 – 23

R2,772 ZAR per night

Home in Gloversville

4.97 out of 5 average rating, 314 reviews

Indoor Heated Pool in the Adirondacks

Year round indoor pool house that is 2000 square feet located in the lower adirondacks. There are several outdoor activities to do in the area...fishing, boating, hiking, kayaking, snowmobiling,cross country skiing & restaurants. Check out my guidebook with things to do in and around the area including near by lakes and restaurants on the lakes. Spend the day exploring and then come back to relax in the warmth of your very own private pool, sit by a fire on the patio or start the grill.

Apr 2 – 9

R3,920 ZAR per night

Home in Woodstock

4.98 out of 5 average rating, 100 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 22 – 29

R15,288 ZAR 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.

Sep 26 – Oct 3

R3,498 ZAR 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.

Nov 9 – 16

R2,445 ZAR per night

Guesthouse in Lenox

4.95 out of 5 average rating, 283 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 4 – 11

R2,731 ZAR 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.

May 6 – 13

R5,917 ZAR 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.

Sep 18 – 25

R8,743 ZAR per night

Apartment in Enfield

4.99 out of 5 average rating, 143 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.

Mar 14 – 21

R1,894 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for The Berkshires rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Oct 20 – 27

R15,068 ZAR per night

Home in New Paltz

4.98 out of 5 average rating, 436 reviews

midcentury modern in ground pool walk 2 trail/town

Sep 6 – 13

R17,506 ZAR 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

R10,809 ZAR per night

Home in Cheshire

5.0 out of 5 average rating, 118 reviews

Pool House

Nov 21 – 28

R2,714 ZAR per night

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Oct 25 – Nov 1

R10,371 ZAR per night

Home in Saugerties

5.0 out of 5 average rating, 132 reviews

Upstate Modern Scandinavian Barn in the Catskills

Dec 20 – 27

R12,918 ZAR per night

Home in Saugerties

4.96 out of 5 average rating, 150 reviews

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

Oct 17 – 24

R21,416 ZAR per night

Home in Woodstock

4.91 out of 5 average rating, 210 reviews

Japanese Teahouse & Onsen, outside shower, tennis

Dec 13 – 20

R4,227 ZAR 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 23 – 30

R1,662 ZAR per night

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Nov 6 – 13

R3,031 ZAR per night

Condo in Windham

4.74 out of 5 average rating, 243 reviews

Summer getaway w/Pool & Tennis Court

Sep 16 – 23

R2,542 ZAR per night

Condo in Stratton

4.96 out of 5 average rating, 118 reviews

Cozy condo within walking distance to the slopes.

Jun 13 – 20

R2,594 ZAR per night

Condo in Dover

4.99 out of 5 average rating, 100 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Oct 4 – 11

R3,178 ZAR per night

Condo in Dover

4.99 out of 5 average rating, 105 reviews

*Mountain Oasis: Base of Mount Snow Retreat*

Dec 3 – 10

R7,900 ZAR per night

Condo in Stratton

4.88 out of 5 average rating, 107 reviews

Perfect Location! Steps to Village and Mountain

Aug 20 – 27

R2,987 ZAR per night

Condo in Hancock

4.9 out of 5 average rating, 51 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Sep 18 – 25

R2,541 ZAR 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

R11,554 ZAR per night

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Aug 26 – Sep 2

R16,698 ZAR per night

Villa in Coxsackie

4.99 out of 5 average rating, 80 reviews

Magnificent Hudson River Estate with Infinity Pool and Spa

Feb 22 – Mar 1

R21,580 ZAR per night

Home in Woodstock

4.6 out of 5 average rating, 10 reviews

Luxury Retreat in the Catskills

Aug 29 – Sep 5

R21,416 ZAR per night

Home in Lanesville

4.77 out of 5 average rating, 205 reviews

Go Hiking and Skiing from a Family-Friendly Farmhouse

Mar 10 – 17

R8,004 ZAR per night

Home in Rhinebeck

5.0 out of 5 average rating, 65 reviews

Rhinebeck Country Living with a Modern Twist

Jun 26 – Jul 3

R13,376 ZAR per night

Destinations to explore