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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

4.85 out of 5 average rating, 260 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 suite in Richmond

4.94 out of 5 average rating, 32 reviews

Berkshire Mountain Retreat

Studio apartment with private entrance nestled in bucolic Richmond, on a quiet mountain road. Miles of hiking and biking trails out your door. Minutes to Tanglewood, Kripalu and many more amazing Berkshire attractions. Four fantastic ski areas within 30-mile radius. Close to Clark Art Museum, Mass MoCA, Appalachian Trail, & the Mass Audubon Wildlife Sanctuary. A short drive to Lenox, Stockbridge, and Great Barrington where shopping and fine dining await . Your relaxing vacation begins here!

Home in Canaan

4.71 out of 5 average rating, 59 reviews

Private estate with Hot Tub, Tennis Court & Pool

Private estate in the Berkshires with 13 acres, 4 bedrooms, private pool + salt water hot tub (all year) indoor + outdoor fire pits, and sunset mountain views. Perfect for larger family vacations, group trips and special occasions. Located in the Berkshires, you'll be close to outdoor adventures, hiking trails (Mt Greylock) and art, theater, dance, music, film, and history. Kayak or swim at the local lake. - By the Jiminy Peak Bosquet ski resorts - 15 mins from Tanglewood and Jacobs Pillow.

Home in Pittsfield

4.97 out of 5 average rating, 60 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.

Home in Egremont

5 out of 5 average rating, 14 reviews

The Catamount 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!

Home in Pittsfield

4.98 out of 5 average rating, 55 reviews

Palatial, central Berkshire, large family home

Welcome to The Manor - your escape to the beautiful and serene Berkshires. You will enjoy the perfect retreat away from the hustle and bustle with this spacious and well decorated 5-bedroom house featuring a pool, quiet surroundings, and easy access to nearby attractions like Tanglewood, Mass MoCA, The Norman Rockwell Museum, ski resorts and world class restaurants. Perfect for families and friends looking to get away and spend quality time with each other. We look forward to seeing you!

Condo in Hancock

4.84 out of 5 average rating, 139 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.

Home in Lanesborough

5 out of 5 average rating, 10 reviews

Berkshire Mountain House

Bring the whole family to this beautiful home in the woods, just minutes from Mt Greylock hiking, Jiminy Peak skiing, local farms and activities. There's truly something for everyone. Go for pumpkin picking and hayrides at Whitney's Farm or walk/bike Ashuwillticook Rail Trail. We are 10 minutes to Pittsfield and 15 minutes to Williamstown. You could have a great time never even leaving the house, while grilling outside, watching movies in the home theater, or cooking in a chef's kitchen.

Home in Great Barrington

5 out of 5 average rating, 58 reviews

Stunning luxury home with fire pit

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!

Bungalow in Great Barrington

4.91 out of 5 average rating, 115 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!

Home in Lanesborough

5 out of 5 average rating, 7 reviews

Mountain Blossom Retreat by Evergreen Home

This centrally located property at the base of Mount Greylock offers luxury and tranquility on 60 private acres with sweeping mountain views. Nestled amidst a botanical garden setting, this 3-bed, 3.5-bath haven boasts amenities including a heated pool, hot tub, central AC, covered walk-around deck and full gym. Enjoy 40 wooded acres, a pond, meadow, hiking trails, and year-round stream. With total privacy and serene mountain vistas, it's your retreat in nature's embrace.

Guesthouse in Williamstown

4.93 out of 5 average rating, 234 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.

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Popular amenities for Berkshire County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Pittsfield

4.94 out of 5 average rating, 16 reviews

Berkshire Lakeside Retreat

Home in Hancock

5 out of 5 average rating, 11 reviews

Bougie B's Mountainside Getaway

Home in Canaan

4.99 out of 5 average rating, 81 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

Home in Great Barrington

5 out of 5 average rating, 10 reviews

Berkshires Estate w/ Heated Pool by Evergreen Home

Home in Lee

4.99 out of 5 average rating, 74 reviews

Berkshire Vacation Home in Lee

Home in Hillsdale

4.88 out of 5 average rating, 26 reviews

Panoramic Hilltop Views w/ Pool near Catamount

Home in New Marlborough

5 out of 5 average rating, 16 reviews

Hot tub, Wood-Burning FP, Sauna: Ready for ski!

Home in Cheshire

4.93 out of 5 average rating, 69 reviews

Berkshire County modern home + pool

Condo rentals with a pool

Condo in Hancock

5 out of 5 average rating, 6 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

Condo in Hancock

4.98 out of 5 average rating, 42 reviews

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

Condo in New Ashford

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Condo in Hancock

4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

Condo in Williamstown

Vacation Village in the Berkshires Resort Suite B

Condo in Hancock

4.62 out of 5 average rating, 143 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Condo in Hancock

4.91 out of 5 average rating, 54 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Condo in Hancock

4.8 out of 5 average rating, 5 reviews

Ski-in/Ski-Out on Jiminy Peak

Destinations to explore