Holiday rentals with a pool in Berkshire County

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!

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!

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

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.

Poolside Woodlawn Getaway

Book your getaway today to Long Pond Luxe in the Berkshires! This recently renovated home features a 3bd / 3 bath main house and a charming pool house for the inlaws or the teenagers that want their own space. Relax by the pool tucked into the full patio, perfect for entertaining in a private woodsy setting just outside Downtown Great Barrington. Whether it's outdoor adventures or relaxing getaways, this peaceful spot has everything you could ask for in a fun, memorable Berkshires escape!

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.

Stylish Rural Sanctuary! (+ Summer Pool)

Recently re-opened for short term stays! Just minutes from Chatham, NY, and nestled in the heart of the Hudson Valley, this serene home on over 8 acres offers breathtaking mountain views. Impeccably renovated in 2022, it seamlessly blends the charm of 18th-century Shaker architecture with the sleek elegance of modern Scandinavian design. Indulge in lightning-fast fiber internet, large smart TV, top-tier appliances, including a Miele fridge, Bertazzoni stove, Bosch dishwasher, and more!

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 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!

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.

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.