Vacation rentals with a pool in Berkshire County

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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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Top guest favorite

A spacious kitchen is designed with rustic wooden beams and modern appliances. Natural light enters through a large window, illuminating marble countertops and a farmhouse-style island. Open shelving displays white dishware, while a wooden table adds warmth to the functional space.

Home in Egremont

5 out of 5 average rating, 28 reviews

Luxury Retreat | Sleeps 18, Butterfly Garden, Pool

This stunning 6 bedroom, 5.5 bath home is the perfect blend of charm, privacy, and modern comfort. Thoughtfully designed with three separate wings, it never feels crowded, even with space for up to 16 guests. Lovingly adorned with original art, colorful textiles, and cozy decor, every corner radiates warmth and tasteful personality, making it a truly wonderful stay. *Sauna & jacuzzi w/ mountain views *Gourmet kitchen *Stone patio w/ BBQs and smoker *Butterfly garden *Tesla charger *Laundry room

Guest favorite

A clear blue swimming pool is surrounded by a concrete deck, with lush greenery and tall trees visible in the background. The pool's water shimmers under the sunlight, reflecting the blue sky and scattered clouds.

Guesthouse in Lenox

4.93 out of 5 average rating, 390 reviews

Restored 1735 Granary I King Bed + Views & Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 20-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

Top guest favorite

An aerial view of the estate highlights a spacious home nestled among trees, featuring a large swimming pool surrounded by a landscaped area. A hot tub is visible on a raised deck, creating an appealing outdoor retreat.

Home in Lanesborough

5 out of 5 average rating, 19 reviews

Mountain Serenity 20 Acres, Hot Tub, Jiminy<10min

Private Berkshires 20Acre estate designed by acclaimed architect and author Norton Juster. An exclusive 4 bedroom retreat, with mountain views from every room, cathedral ceilings, cozy fireplaces, elegant living spaces, and outdoor fire pit, it’s the perfect place to unwind. Relax in the hot tub or sauna after a day of skiing at Jiminy Peak or Bousquet. Newly renovated with high end furnishings and chef's kitchen. A perfect mix of adventure and tranquility awaits—book your mountain escape today!

Guest favorite

Home in Pittsfield

4.96 out of 5 average rating, 80 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.

Top guest favorite

A spacious open-plan living area is showcased, featuring large windows that invite natural light. A modern sectional sofa in warm tones is arranged around a low table. A dining area with a long table and dining chairs is visible in the background, enhancing the inviting atmosphere.

Home in Egremont

5 out of 5 average rating, 38 reviews

The Catamount Ski Haus with 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

The guesthouse stands adjacent to a refreshing unheated saltwater pool, with a surrounding patio featuring lounge chairs and an umbrella for shade. Lush greenery complements the rustic charm of the barn-style structure. The expansive sky is dotted with soft clouds, enhancing the serene outdoor atmosphere.

Guesthouse in Great Barrington

4.9 out of 5 average rating, 84 reviews

Barn Guesthouse w/ pool

Come enjoy our renovated Barn Guesthouse. Originally a part of the 250+ year old farm and property, the updated Barn offers sunset views of the surrounding meadows, a private bedroom, outdoor shower, and unheated saltwater pool in the summer months (Memorial Day weekend - Sept 15). A great place to come relax after a day adventuring around the Berkshires. Just 15 minutes to Great Barrington, 20 minutes to Stockbridge, you can enjoy the local scene as well as a quintessential country setting.

Guest favorite

Home in East Chatham

5 out of 5 average rating, 9 reviews

Red Rock Summit: Mtn Escape w/ Pool, Pond + Views

Welcome to Red Rock Summit, where well-designed living takes advantage of majestic mountain views at every turn. This contemporary 4-bedroom, 4-bathroom home on 80 impressive acres is just 2.5-hrs from NYC & Boston. Enjoy open plan, bright and airy interiors and abundant outdoor amenities including a large pool, serene swimmable pond and a firepit. Explore the nearby Village for shopping and dining, or hit the slopes at Catamount Ski Area. Welcome to a mountain retreat like no other.

Superhost

A private in-ground pool is surrounded by a spacious wooden deck, equipped with several lounge chairs for relaxation. Tall trees provide a natural backdrop, enhancing the secluded atmosphere of the outdoor space.

Home in East Chatham

4.96 out of 5 average rating, 23 reviews

Luxury Mountain Home 6BR, 4 ski mtns, fireplace

A getaway at the edge of the Berkshires - family friendly, 4 ski mountains nearby, charming towns, fireplace, expansive deck, sunset views, private in-ground pool, BBQ, secluded, wooded, nearby lakes, hiking, Tanglewood for summer music and performance festivals. We've set up this vacation home for ourselves to enjoy, so you know we've put our hearts into it and are excited for you to create memories for a lifetime. The home is set up beautifully for families and groups of friends.

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, 75 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

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, 223 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.

Guest favorite

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

4.95 out of 5 average rating, 108 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Guest favorite

A serene pool area features a large in-ground pool surrounded by lush greenery. Several lounge chairs, including two green loungers and a round table with chairs, are situated on the patio. A bright red umbrella provides shaded seating, adding to the inviting outdoor space.

Guesthouse in Williamstown

4.93 out of 5 average rating, 244 reviews

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse 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.