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Vacation rentals with a pool in Berkshire County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Berkshire County

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, 237 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.

Jul 29 – Aug 5

G$55,848 GYD per night

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private downstairs apartment with your own entrance. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. Upstairs is my family- a 6 year old boy and medium-sized dog- you will hear us! Sometimes we have friends and family visiting. In the summer you may see us at the pool with them. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :-)

Sep 30 – Oct 7

G$27,529 GYD per night

Villa in Pittsfield

4.93 out of 5 average rating, 30 reviews

Luxurious Berkshire Mountain Retreat!!

Escape to the Berkshires at this 2 acre, private retreat. Gleaming hardwood floors, handmade Amish furniture, large interior and exterior areas for family activities as well as a heated in-ground pool with a slide for the kids that is open during the summer months! Given the 4 bedrooms and additional sleeping areas, this spacious ranch is suited for up to 6-8 guests with the ability to host more (there is a 1 bedroom pool house that can sleep an additional 2 guests for an additional charge).

Oct 15 – 22

G$168,720 GYD per night

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

May 28 – Jun 4

G$33,701 GYD per night

Apartment in Great Barrington

5.0 out of 5 average rating, 15 reviews

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Mar 9 – 16

G$35,699 GYD per night

Bungalow in Great Barrington

4.91 out of 5 average rating, 109 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

Jun 2 – 9

G$108,256 GYD 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 8 – 15

G$39,217 GYD per night

Bungalow in Williamstown

4.89 out of 5 average rating, 202 reviews

Hollywood Bungalow in the Berkshires

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Dec 4 – 11

G$48,965 GYD per night

Home in Sheffield

4.85 out of 5 average rating, 114 reviews

Race Mountain House

High on the slopes of Race Mountain, this spacious 4-bedroom villa offers sweeping east-facing views. In the early hours, the house floods with morning light and sunrises are spectacular. The inviting, creative design invokes a true sense of retreat. Swimming Pool is available at the neighboring Race Brook Lodge... and Mountain House guests get a discount at The Stagecoach Tavern restaurant. Due to Covid19 restrictions, parties and events are not permitted.

Jul 8 – 15

G$115,741 GYD per night

Apartment in Adams

4.88 out of 5 average rating, 58 reviews

Mountain Living, 1-bedroom unit, outdoor hot-tub

Relax & enjoy nature in this tranquil, 1 bedroom unit down the block from Mt. Greylock, highest mountain in MA! 2 minutes away from hiking trails, 10 minutes away from Mass Moca, 25 minutes away from Jiminy Peak ski resort. Enjoy MT Views, and jump in the outdoor jacuzzi right outside your bedroom. WiFi, AC, your own thermostat & TV. The suite you’ll be staying in is directly attached but separate access from the main house. Military and HCP discounts

Aug 5 – 12

G$19,369 GYD per night

Guesthouse in Lenox

4.95 out of 5 average rating, 281 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

G$30,485 GYD per night

Home in West Stockbridge

4.97 out of 5 average rating, 58 reviews

Panoramic Views, Indoor Pool by Evergreen Home

An ideal retreat nestled in the Berkshires with vast, expansive panoramic views. With 4 BR, 4.5 BA, a brand new gorgeous kitchen, gas fireplace & indoor pool, this home is the perfect escape with family & friends! Centrally located 12 minutes to Tanglewood, Shakespeare & Co, Berkshire Botanical Gardens, The Mount, Norman Rockwell Museum. Conveniently situated just minutes away from all the Berkshires has to offer. Welcome to your home away from home.

Dec 14 – 21

G$239,521 GYD 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

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Berkshire County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Cheshire

4.94 out of 5 average rating, 50 reviews

Berkshire County modern home + pool

Mar 14 – 21

G$91,117 GYD per night

Home in Dalton

4.89 out of 5 average rating, 80 reviews

Private & Stylish Berkshires House for All Seasons

Jun 10 – 17

G$90,981 GYD per night

Home in Sheffield

4.94 out of 5 average rating, 16 reviews

Private Berkshire County Retreat

Jun 10 – 17

G$97,416 GYD per night

Home in New Marlborough

4.95 out of 5 average rating, 21 reviews

Berkshires Colonial Farmhouse

Dec 11 – 18

G$104,930 GYD per night

Home in Great Barrington

5.0 out of 5 average rating, 52 reviews

Stunning luxury home with pool

Sep 28 – Oct 5

G$162,225 GYD per night

Home in Pittsfield

4.97 out of 5 average rating, 38 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

Dec 9 – 16

G$144,341 GYD per night

Home in Pittsfield

5.0 out of 5 average rating, 41 reviews

Stunning Berkshires Retreat, Large and Private

Sep 26 – Oct 3

G$151,726 GYD per night

Home in Great Barrington

5.0 out of 5 average rating, 35 reviews

Six-bedroom country house with pool and hot tub

Apr 1 – 8

G$239,592 GYD per night

Condo rentals with a pool

Condo in Hancock

4.9 out of 5 average rating, 21 reviews

All-season Berkshires ski resort condo - Sitzmark

Oct 19 – 26

G$37,618 GYD per night

Condo in Hancock

4.95 out of 5 average rating, 19 reviews

Upscale 2 bed/2bath Condo at a Mountain Resort!

Oct 12 – 19

G$67,255 GYD per night

Condo in Hancock

4.93 out of 5 average rating, 15 reviews

Large one bedroom, two full bath, full kitchen

Jul 4 – 11

G$35,740 GYD per night

Condo in Hancock

4.93 out of 5 average rating, 58 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

Oct 20 – 27

G$55,275 GYD per night

Condo in Hancock

4.97 out of 5 average rating, 37 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Jan 5 – 12

G$110,665 GYD per night

Condo in Hancock

4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

Mar 5 – 12

G$75,917 GYD per night

Condo in New Ashford

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Nov 5 – 12

G$35,046 GYD per night

Condo in Hancock

4.62 out of 5 average rating, 138 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Aug 6 – 13

G$27,057 GYD per night

Destinations to explore