Ferienunterkünfte mit Pool in Berkshire County

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.

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!

Restored 1735 Granary I Mountain Views + Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 20-ft cedar-lined ceilings, original wide-plank pine 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 and standing shower. Minutes to Lenox, Tanglewood, scenic trails, and local farms. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

Berkshires Oasis Retreat: Art Meets Nature

Our enchanting home is nestled on 8 acres of lush woods and blends tranquility and modern comfort with exquisite landscaping & outdoor sculptures. The open floorplan boasts of artistic touches, contemporary design and a wall of windows. Imagine sipping coffee on the deck, enjoying drinks by the pool or reading while on the large sofa by the gas fireplace! If you are seeking a perfect escape near all Berkshires must-go destinations... Your Otis getaway awaits – embrace the extraordinary!

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!

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.

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.

Hillsdale Escape | Pool, Hot Tub, Game Room

Escape to this beautifully restored 7BR farmhouse nestled in the rolling hills of Hillsdale. Just minutes from Catamount ski area and close to Great Barrington, this spacious retreat features a private pool, 7-person hot tub, arcade game room, fire pit, and chef’s kitchen. Ideal for family reunions, group getaways, team business trips, or peaceful weekends in nature -complete with fast Wi-Fi, Smart TVs, and room for 14+ guests.