Vacation rentals with a pool in Berkshire County

Red Rock Summit: Pool | Privacy + Views | Sauna

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, barrel sauna, 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 o

Modern Log Cabin w/Pool & Views By Evergreen Home

15 MINUTES TO BUTTERNUT SKI AREA Welcome to your private Berkshire escape with a heated saltwater pool, hot tub, mountain views, and refined rustic charm. This 3-bedroom (5 bed), 3.5-bath modern log cabin offers a great room with stone fireplace, open kitchen, screened porch, and spacious suites. Outside, enjoy a seasonal heated saltwater pool, fire pit, gardens, and pool house. Located just minutes from downtown West Stockbridge and a short drive to Lenox, Stockbridge, and Great Barrington.

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!

Spacious 4BR Central-Berkshires Home with POOL!

Spacious and comfortable home in a serene setting and ideal location. Whether you are coming for performing arts, museums, skiing, hiking, dining, shopping or some combo of adventure, this home is conveniently located plus only minutes from the Mass Pike exit in Lee, groceries, Lee Outlets and more!! Relax by the pool, grill outdoors and enjoy cooking in the well-outfitted kitchen. Enjoy walks and the vistas along the quiet country road. Well-behaved pets welcomed on a case-by-case basis.

"The Cabin" - Cozy & Rustic Home (Averill Park)

This luxurious log cabin, nestled on 200+ acres of private, expansive wilderness, is the perfect escape. Enjoy sunrise from the front porch, grill on the back deck and explore the 18-hole disc golf course, tranquil Japanese garden, croquet court, swimming pool and multiple walking trails throughout the forest property. Jiminy Peak Ski Resort, the Berkshires, and Saratoga Springs are all nearby. All amenities are provided with a personal touch that will make your stay relaxed and memorable.

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. Or 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.

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!

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.

New-Modern! Guesthouse near Berkshire Skiing

Tucked away on 10 peaceful acres in the Berkshires/Hudson Valley, our guesthouse is a cozy, design-forward escape surrounded by nature. Sip coffee on the deck or curl up with views of pastures and woods. In autumn, enjoy brilliant foliage and crisp air. In winter sleep in and relax or head to Jiminy Peak or Bousquet for skiing, snowshoe nearby trails, or explore Lenox, Chatham, and Great Barrington. A perfect setting to rest, recharge, and savor the beauty of the season.

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.

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy 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 & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Sweet Dreams Retreat

Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.