Find the best hotels in The Berkshires

Vacation Village in the Berkshires
★★★★★
Hancock
👨‍👩‍👧‍👦Category.suitable_for
Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities. The Vacation Village in the Berkshires ideally places guests only moments away from a variety of activities, historical sites and delicious dining options. Biking trails, top-rate ski trails, fishing and swimming are all nearby. Guests can also enjoy the variety of amenities available at the Berkshires Village. The property features a state-of-the-art fitness center, private balconies and patios and fully and partially equipped kitchens. Jiminy Peak Mountain Ski Resort is 1.6 mi away from this hotel.
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✓ Free cancellation
✓ No prepayment needed — pay at the property
8.6
Excellent
1,437 reviews

Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires
★★★
South Lee
👨‍👩‍👧‍👦Category.suitable_for
Located in South Lee and within 5 mi of Norman Rockwell Museum, Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires has barbecue facilities and nonsmoking rooms. Featuring family rooms, this property also provides a seasonal outdoor pool, an indoor pool, a fitness center and a bar. All rooms feature a flat-screen TV, a seating area, a kitchen and a private bathroom. Free WiFi is available. Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires also provides guests with a children's playground. Adams is 25 mi from the accommodations. The nearest airport is Bradley International Airport, 38 mi from the property.
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✓ Free cancellation
✓ No prepayment needed — pay at the property
8.9
Excellent
693 reviews

The Yankee, Trademark Collection by Wyndham
★★★
Lenox
💼Category.suitable_for
Nestled on a 111-acre wildlife sanctuary and surrounded by the beauty of the Berkshires, The Yankee, Trademark Collection by Wyndham provides a welcoming stay by the famous Appalachian Trail in October Mountain State Forest. This contemporary, nonsmoking hotel is near plenty of restaurants as well as Tanglewood, Jacob’s Pillow, and MASS MoCA. Admire original work at the Norman Rockwell Museum, 19th century paintings at The Clark, and stunning fall foliage in Mount Greylock State Reservation. Albany International Airport (ALB) is 48 miles away.
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✓ Free cancellation
✓ No prepayment needed — pay at the property
8.6
Excellent
750 reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG
★★★★
Pittsfield
💼Category.suitable_for
Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts. We are 10 minutes driving time to many corporations such as General Dynamics, Lenco Armored Cars, Lockheed Martin. When you have time to relax at the hotel take advantage of our fitness center, heated indoor pool and the 101 Restaurant for Breakfast or Dinner. The hotel is located centrally to many attractions in the Berkshires such as Tanglewood, Norman Rockwell, Hancock Shaker Village, Mass Moca, Clark Art Museum, Herman Melville, Jacob Pillow, Barrington Stage and the Colonial Theater. When it is time to bring home some gifts there are many antiques shops, specialty shops in every town in the Berkshires plus there is the Lee Premium Outlet to score some great deals. We look forward to your visit and until you walk through our doors, have a great day!
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✓ Free cancellation
✓ No prepayment needed — pay at the property
7.8
Very good
244 reviews

Maple Terrace Motel
★★★
Williamstown
🚗Category.suitable_for
Nestled among the Berkshires, this 3 acre property features mountain views and free WiFi access. This Williamstown, Massachusetts motel is less than half a mile from Williams College. Each guest room at the Maple Terrace Motel features cable TV with DVD player, a writing desk, and a refrigerator. A telephone and coffee-making facilities are also available. They are decorated in light colors and dark wood furnishings. Windows in the front and the back of the rooms provide a lot of daylight. An outdoor heated pool is available seasonally at the Motel Maple Terrace. Guests can relax in the garden area or enjoy mountain views from the picnic area. A continental breakfast is available in the reception area. Jiminy Peak Mountain Resort is 14 miles from the Maple Terrace. Waubeeka Golf Links is 10 minutes’ drive away.
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✓ Free cancellation
✓ No prepayment needed — pay at the property
9.1
Fantastic
307 reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel
★★★
Lee
💼Category.suitable_for
The Black Swan Inn, Ascend Hotel Collection is conveniently located in the foothills of the Berkshire Mountains. The hotel is close to several area attractions and local points of interest like Tanglewood Music Festival, Norman Rockwell Museum and Jacob's Pillow. The Berkshires is an area rich in outdoor recreational opportunities. Enjoy the sparkling Laurel Lake right in the hotel's backyard where you can go swimming, fishing or boating. Several golf courses, ski slopes and parks are close to the hotel. Stay with us and ski at Ski Butternut. Spend the day shopping for that must-have item at the Lee Premium Outlets. Relax with a delicious meal or cocktail at the Bombay Bar & Grill, located on the premises and watch the sun set over the lake after a full day of activities in the Berkshires. Guests of The Black Swan Inn, Ascend Hotel Collection are invited to enjoy amenities like free wireless high-speed Internet access and free local calls. All spacious guest rooms of this Massachusetts hotel are nonsmoking and are equipped with refrigerators, Keurig coffee makers, hair dryers, irons, ironing boards, desks and cable TV. Some rooms feature balconies and whirlpool bathtubs.
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✓ Free cancellation
✓ No prepayment needed — pay at the property
8.7
Excellent
537 reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
★★
Pittsfield
🚗Category.suitable_for
Your Gateway to Relaxation and Adventure in the Heart of the Berkshires Discover the perfect home base for your next getaway at our brand-new hotel, nestled in the scenic Berkshires of Western Massachusetts. Whether you're here for a peaceful weekend escape, a family adventure, or a couples retreat, we offer everything you need to rest, recharge, and explore. Start Your Day Right: Every morning begins with our complimentary Express Start™ breakfast, featuring hot options, fresh fruit, and grab-and-go choices—perfect fuel before a day of exploring. Leisure-Focused Amenities: Heated Indoor Pool – Open daily for a refreshing dip or family splash time. Fitness Center – Stay active with cardio equipment and weights. EV Charging Stations – Convenient for eco-conscious road trippers. Pet-Friendly Rooms – Bring your four-legged family members along. Complimentary Parking – No stress, no extra fees. Explore the Berkshires: Step outside and you're just minutes from the region’s top attractions: Hiking trails with stunning mountain views Tanglewood and live music venues Norman Rockwell Museum, Hancock Shaker Village, and more Charming small towns, art galleries, and farm-to-table dining The Perfect Berkshires Base: Whether you're here for leaf-peeping, skiing, summer concerts, or just some well-earned R&R, our central location in Pittsfield makes exploring easy and relaxing.
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✓ Free cancellation
✓ No prepayment needed — pay at the property
9.2
Fantastic
43 reviews

The Cornell Inn, Lenox & The Berkshires
★★★
Lenox
💼Category.suitable_for
Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee machines. Many rooms feature fireplaces and private balconies. The Boston Symphony Orchestra's Tangle wood Institute is five minutes away, and the restaurants of Lenox are 1 minute away. A table-served gourmet breakfast (not a buffet) is included with your room, and it includes your choice of espressos, cappuccinos, lattes, Americano, regular coffee, or imported chocolate hot chocolate. Guests can relax on our private deck next to a koi pond and waterfall, or enjoy the gardens that connect directly to the beautiful Kennedy Park. The Cornell is within 1 mile of shopping and dining. Bouquet Ski Area and Berkshire Scenic Railway Museum are 10 minutes’ drive.
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✓ No prepayment needed — pay at the property
8.9
Excellent
550 reviews