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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, 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

$387 CAD per night

Guest favourite

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. 10 – 17

$243 CAD per night

Guest favourite

Home in Lenox

4.96 out of 5 average rating, 24 reviews

Lenox Grand Colonial with Pool by Evergreen Home

This 4 bedroom spacious home sits on a quiet cul-de-sac beneath October Mountain, with a picturesque back yard complete with in-ground pool. The property abuts a 10-acre “meditation meadow” for all-season enjoyment. Just 10 minutes to downtown Lenox & Tanglewood, so close to everything the Berkshires has to offer! The convenience of shops and restaurants just 2 minutes away. Your family will be close to everything when you stay at this centrally located spot in the heart of the Berkshires!

Sep. 11 – 18

$753 CAD per night

Guest favourite

Apartment in Great Barrington

5.0 out of 5 average rating, 12 reviews

King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires

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 KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Youtube TV with NFL Pack

Jun. 1 – 8

$247 CAD per night

Guest favourite

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).

Jul. 15 – 22

$1,305 CAD per night

Guest favourite

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.

Nov. 6 – 13

$262 CAD per night

Guest favourite

Vacation home in Hancock

5.0 out of 5 average rating, 8 reviews

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

*NEW to AirBnB* Book today and spend your ski days only steps from the lift! Get first tracks or even night ski from this one bedroom condo in Building 1 at The Country Inn at Jiminy Peak. Private parking, kitchenette, and all of the comforts of home. Visit any season to explore this beautiful Berkshire mountain. Enjoy private, gated parking, walk to the country store to get essentials, and even rent equipment right at the mountain. A family-friendly condo with food options for all.

Nov. 25 – Dec. 2

$250 CAD per night

Guest favourite

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. 5 – 12

$855 CAD per night

Guest favourite

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

$296 CAD per night

Guest favourite

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.

Sep. 11 – 18

$385 CAD 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.

Oct. 15 – 22

$891 CAD per night

Guest favourite

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

Sep. 22 – 29

$164 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Berkshire County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Cheshire

4.94 out of 5 average rating, 50 reviews

Berkshire County modern home + pool

Jun. 12 – 19

$800 CAD per night

Home in Dalton

4.89 out of 5 average rating, 81 reviews

Private & Stylish Berkshires House for All Seasons

May 7 – 14

$680 CAD per night

Guest favourite

Home in Lee

4.98 out of 5 average rating, 62 reviews

Berkshire Vacation Home in Lee (Pool Opens in May)

Oct. 17 – 24

$642 CAD per night

Guest favourite

Home in Great Barrington

4.97 out of 5 average rating, 34 reviews

Newly Remodeled Private Estate-Pool, Tennis Court!

Nov. 28 – Dec. 5

$1,735 CAD per night

Guest favourite

Home in New Marlborough

4.95 out of 5 average rating, 21 reviews

Berkshires Colonial Farmhouse

Dec. 1 – 8

$804 CAD per night

Guest favourite

Home in Great Barrington

5.0 out of 5 average rating, 52 reviews

Stunning luxury home with pool

Nov. 7 – 14

$1,466 CAD per night

Guest favourite

Home in West Stockbridge

5.0 out of 5 average rating, 6 reviews

Pool is open Memorial Day Weekend! - Sleeps 13!

Oct. 29 – Nov. 5

$1,041 CAD per night

Guest favourite

Home in Pittsfield

4.97 out of 5 average rating, 39 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

Nov. 11 – 18

$1,136 CAD per night

Condo rentals with a pool

Guest favourite

Condo in Hancock

4.95 out of 5 average rating, 19 reviews

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

Nov. 30 – Dec. 7

$442 CAD per night

Guest favourite

Condo in Hancock

4.9 out of 5 average rating, 21 reviews

All-season Berkshires ski resort condo - Sitzmark

Aug. 2 – 9

$321 CAD per night

Guest favourite

Condo in Hancock

4.96 out of 5 average rating, 27 reviews

Ski - IN ski - out Lift&MT.VIEWS GR8 4 Season LOC.Unit2

May 6 – 13

$320 CAD per night

Guest favourite

Condo in Hancock

4.95 out of 5 average rating, 22 reviews

Jiminy Peak Apartment

May 17 – 24

$268 CAD per night

Guest favourite

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. 8 – 15

$838 CAD per night

Guest favourite

Condo in Hancock

4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

Mar. 8 – 15

$573 CAD per night

Condo in New Ashford

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Sep. 9 – 16

$334 CAD per night

Condo in Hancock

4.62 out of 5 average rating, 138 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Aug. 9 – 16

$215 CAD per night

Destinations to explore