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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in New Lebanon

4.98 out of 5 average rating, 59 reviews

Berkshire Mountain home views, pool, Queechy Lake

Summer Paradise in the Berkshires! Secluded home on 11 acres, surrounded by farmland. Perfect house for families to share! Enjoy beautiful view of Berkshire mountains while sitting on expansive deck or in bright,sunny screened-in sunroom. Heated, 20x40 inground salt water pool. Membership to Queechy Lake included! Walk to Corkscrew Rail trail, 5 miles of flat, wooded trail perfect for biking, walking, running, exploring. Close to all Berkshire attractions especially Jiminy Peak/Tangelwood

Superhost

Cabin in Stephentown

4.86 out of 5 average rating, 285 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.

Guest favorite

A circular in-ground pool is surrounded by a paved deck, featuring potted plants and flowers that add greenery to the space. Colorful lounge chairs are positioned around the pool, providing a relaxing area for guests. A serene backdrop of trees completes the setting.

Apartment in Pittsfield

4.97 out of 5 average rating, 70 reviews

*Berkshire's Sweet Spot-Close to ski/Spa open

The Berkshire's Sweet Spot 2 property is an entire half of a duplex apartment located in central Berkshire County within walking distance to downtown. Renting both sides of the home may be an option. They are recently updated for your comfort with newer kitchens, baths and new smart televisions. The location can't be beat for seeing all of the Berkshire's attractions. The neighborhood is very peaceful, quiet and safe. Enjoy your own private oasis with seasonal in ground pool and year round Spa!

Guest favorite

Home in Pittsfield

4.96 out of 5 average rating, 71 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my newly renovated home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room or master bed & enjoy the cozy ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Superhost

Home in Egremont

5 out of 5 average rating, 4 reviews

Fabulous Heated Pool, Screen Porch, Ping Pong!

Stone Hill is an immaculate property with big views! Amenities include: 3+ bedrooms, 3 full baths, sleeps 9 max. High speed internet/wifi, central AC, lovely gas fireplace, all stainless Bosch appliances and a gas range, heated pool with several areas of outdoor furniture, propane BBQ grill, sun deck, 3-season sunny screened porch/sunroom, 2-car garage, gym, ping-pong table, washer/dryer, portable crib, high chair and more! Pet friendly for non-shedding hypoallergenic pets only with pet fee.

Top guest favorite

Home in Egremont

5 out of 5 average rating, 29 reviews

The Catamount Ski Haus w. Pool/Hot Tub

Welcome to the Berkshires! Located almost across the street from the Catamount Ski Resort - come unwind with some fun, peace and adventure. This 4 bedroom 4 bath sits on a 5 acre property nestled amongst the trees with a private pool, hot tub and Mountain View ’s to gaze at. Dine at the quaint, hip restaurant in little cat lodge next to the ski resort, have coffee in Hillsdale at Cook& Larder. Or check out the shops in Great Barrington. There is a ton to do in the Berkshires all year long!

Guest favorite

Condo in Hancock

4.85 out of 5 average rating, 151 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.

Guest favorite

A large country estate is presented, featuring an orange exterior surrounded by lush greenery. The home includes a spacious front entryway with steps leading to double doors, while an expansive driveway and two-car garage are visible on the right.

Home in East Chatham

4.9 out of 5 average rating, 20 reviews

10 Acre Country Estate with Pool, Hot Tub & Views!

Welcome to our serene country estate on a private road with 10 acres! Our home is equipped with a pool, hot tub, mountain view’s, patio, sunroom, 2 fireplaces, and more amenities to make your stay relaxing and memorable. Situated in the Hudson Valley and 10 minutes from the Berkshires, enjoy everything Upstate has to offer with our beautiful property located in the heart of it all. Perfect for large groups of friends for a fun weekend away or big families looking for a change of pace.

Top guest favorite

The serene backyard features a sparkling blue pool surrounded by vibrant landscaping, including colorful flowers. The house, displaying a modern aesthetic, has large windows and a covered patio that invites natural light, set against a backdrop of lush trees.

Home in Great Barrington

4.99 out of 5 average rating, 69 reviews

Stunning luxury home with pool

Welcome to our weekend home in the Berkshires! We now rent it out when we’re not there, following a top-to-bottom renovation with all new furniture, and hope our guests enjoy it as much as we do. Our home is in Great Barrington, 2.5 hours' drive from NYC, surrounded by trees and parkland (Monument Mountain is next door). Yet it's less than 10-15 minutes' drive to town, shopping, restaurants, skiing, and Tanglewood. Come enjoy the Berkshires with complimentary gourmet coffee!

Guest favorite

A spacious outdoor pool is bordered by a secure fence, reflecting the clear blue sky. A red cabin stands in the background, complemented by a lush landscape of trees surrounding the area. The pool area offers a peaceful and inviting atmosphere for relaxation.

Bungalow in Great Barrington

4.91 out of 5 average rating, 117 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!

Guest favorite

The pool area is framed by lush greenery, featuring a large in-ground pool with a slide. A colorful inflatable float is seen in the water. A shaded patio table with chairs provides a space for relaxation, alongside a sun umbrella that casts shade over the area.

Home in Williamstown

4.89 out of 5 average rating, 217 reviews

Hollywood Bungalow in the Berkshires #C0191633410

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.

Top guest favorite

A spacious backyard features a large in-ground pool surrounded by green grass. Chaise lounges with floral cushions are arranged nearby, accompanied by a small table holding drinks. A red shed is visible beyond the pool, framed by lush foliage.

Home in Lenox

4.97 out of 5 average rating, 35 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. 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!