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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, 239 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.

Aug 18 – 25

€ 298 per night

Home in Ghent

4.87 out of 5 average rating, 271 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.

Jan 1 – 8

€ 266 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 14 – 21

€ 160 per night

Farm stay in Red Hook

4.99 out of 5 average rating, 127 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 11 – 18

€ 621 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..

Jan 20 – 27

€ 819 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.

Oct 14 – 21

€ 223 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.

Jan 3 – 10

€ 128 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.

Oct 26 – Nov 2

€ 158 per night

Barn in Hillsdale

4.97 out of 5 average rating, 117 reviews

Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & on a 15-acre hilltop with views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking and tons of games. Perfect for winter sledding right on our hill. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. *Pets must get written approval*

Oct 26 – Nov 2

€ 1,067 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.

Jun 13 – 20

€ 229 per night

Cabin in Red Hook

4.96 out of 5 average rating, 306 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

€ 474 per night

Apartment in Enfield

4.99 out of 5 average rating, 146 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.

Apr 21 – 28

€ 90 per night

Vacation rentals for every style

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Popular amenities for The Berkshires rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Hudson

4.93 out of 5 average rating, 227 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

Sep 13 – 20

€ 571 per night

Home in New Paltz

4.98 out of 5 average rating, 437 reviews

midcentury modern in ground pool walk 2 trail/town

May 30 – Jun 6

€ 659 per night

Home in Gloversville

4.97 out of 5 average rating, 316 reviews

Indoor Heated Pool in the Adirondacks

Apr 16 – 23

€ 233 per night

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Dec 29 – Jan 5

€ 808 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 31 – Nov 7

€ 546 per night

Home in Saugerties

5.0 out of 5 average rating, 132 reviews

Upstate Modern Scandinavian Barn in the Catskills

Sep 17 – 24

€ 703 per night

Home in Woodstock

4.91 out of 5 average rating, 212 reviews

Japanese Teahouse & Onsen, outside shower, tennis

Dec 31 – Jan 7

€ 267 per night

Home in Hudson

5.0 out of 5 average rating, 5 reviews

Gemini House - 1892 Farmhouse w/ Pool in Hudson

Nov 21 – 28

€ 667 per night

Condo rentals with a pool

Condo in Windham

4.89 out of 5 average rating, 134 reviews

Cozy Mountain hideaway Windham, Hunter

Jul 27 – Aug 3

€ 115 per night

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Jun 7 – 14

€ 226 per night

Condo in Windham

4.74 out of 5 average rating, 243 reviews

Summer getaway w/Pool & Tennis Court

Aug 16 – 23

€ 160 per night

Condo in Stratton

4.96 out of 5 average rating, 118 reviews

Cozy condo within walking distance to the slopes.

Jun 26 – Jul 3

€ 164 per night

Condo in Dover

4.99 out of 5 average rating, 100 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Sep 15 – 22

€ 191 per night

Condo in Dover

4.99 out of 5 average rating, 105 reviews

*Summer Mountain Oasis: Base of Mount Snow Retreat

Oct 1 – 8

€ 463 per night

Condo in Stratton

4.88 out of 5 average rating, 107 reviews

Perfect Location! Steps to Village and Mountain

Sep 16 – 23

€ 178 per night

Condo in Dover

4.96 out of 5 average rating, 23 reviews

Ski in Ski out condo great location

Jul 27 – Aug 3

€ 118 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

Oct 22 – 29

€ 633 per night

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

Sep 9 – 16

€ 620 per night

Farm stay in Fleischmanns

4.91 out of 5 average rating, 11 reviews

Escape to a Dreamy 1857 Farmhouse in Fleischmanns

Nov 3 – 10

€ 433 per night

Villa in Coxsackie

4.99 out of 5 average rating, 80 reviews

Magnificent Hudson River Estate with Infinity Pool and Spa

Jan 19 – 26

€ 1,126 per night

Home in Woodstock

4.6 out of 5 average rating, 10 reviews

Luxury Retreat in the Catskills

Sep 4 – 11

€ 1,136 per night

Home in Lanesville

4.77 out of 5 average rating, 205 reviews

Go Hiking and Skiing from a Family-Friendly Farmhouse

Oct 8 – 15

€ 426 per night

Home in Rhinebeck

5.0 out of 5 average rating, 65 reviews

Rhinebeck Country Living with a Modern Twist

Sep 16 – 23

€ 635 per night

Destinations to explore