Hotels in The Berkshires

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Popular hotels in The Berkshires

Discover well-known properties in The Berkshires that are favored by visitors more than others. There are 1,374 hotels in The Berkshires and price data was last updated on August 20, 2025. The average price for a hotel in The Berkshires is .
The following hotels are among the most sought after in the The Berkshires area. Users can utilize the filters available to narrow down their search.
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461 Pittsfield Road, Lenox, MA, United States
Thank you for choosing our The Yankee, Trademark Collection by Wyndham hotel.
Pool
Free Wi-Fi
Parking
8.4
Excellent
1260 reviews
Location
3.4 mi from city centre
30 Main Street, Stockbridge, MA, United States
Historic hotel with 3 restaurants and a fitness center This smoke-free hotel features 3 restaurants, an outdoor pool, and a fitness center. WiFi in public areas is free. Other amenities include a bar/lounge, a 24-hour business center, and coffee/tea in a common area. The Red Lion Inn offers 125 air-conditioned accommodations with DVD players and bathrobes. Beds feature Frette Italian sheets. Cable television is provided. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Housekeeping is offered daily and hypo-allergenic bedding can be requested. Recreational amenities at the hotel include an outdoor pool and a fitness center. The recreational activities listed below are available either on site or nearby; fees may apply.
Free Wi-Fi
Parking
8.2
Excellent
585 reviews
Location
0.6 mi from city centre
190 Meadow Street, Lee, MA, United States
The beautiful Berkshires may remind you of those quintessential Norman Rockwell paintings. But families don’t need to stay “picture-perfect” to have a great time hiking, skiing, rafting or enjoying fall leaves all near the Appalachian Trail. Messy hair and muddy shoes from the great outdoors are the norm here. After a day of exploring, Oak n’ Spruce Resort is the perfect place to kick up your feet and relax. Located in South Lee, near Lenox, MA, Oak n’ Spruce Resort is a family-inspired retreat that features indoor and outdoor pools, an arcade, pool tables, movie theater, 18-hole mini golf course, sports courts and two bars. It’s also at the heart of outdoor fun and cultural attractions. Visit the Norman Rockwell Museum and Tanglewood, the summer home of the Boston Symphony Orchestra. Tap into your adventurous side and go skiing or boating. Take a hike in Mount Greylock State Reservation to reach the highest elevation in the state and fill up your camera roll with brightly colored fall foliage. Or venture out of South Lee and Lenox, MA, and head over to Albany, NY, and Hartford, CT, both about an hour away. Oak n’ Spruce Resort offers spacious one- to three-bedroom villas from 826 to 1,689 square feet. Each comes with extra space in the living room and a full-sized kitchen, along with washers and dryers in select villas. Laundry facilities are also available onsite. Please note there is a resort fee that includes a variety of onsite amenities.
Pool
Free Wi-Fi
Parking
8.8
Excellent
570 reviews
Location
2.5 mi from city centre
1 West Street, Pittsfield, MA, United States
Nestled in the heart of Western Massachusetts, the Berkshires are renowned for their breathtaking mountain landscapes and vibrant cultural scene and live theatre.Such as the Colonial Theatre, Barrington Stage or Tanglewood.Whether you're here to hike the scenic trails of Mount Greylock or the Appalachian Trail, ski the snowy slopes of Jiminy Peak or Bousquet Mountain, the region offers something for everyone year-round. When visiting the Berkshires, our hotel the Holiday Inn and Suites Pittsfield*Berkshires is the perfect home base for both adventure and relaxation. Conveniently located just minutes from major area businesses like Berkshire Health Systems and General Dynamics, as well as top attractions, our hotel caters to both leisure and business travelers.As the largest event facility in the region, the Holiday Inn and Suites Pittsfield*Berkshires boasts 12,000 square feet of versatile banquet space, accommodating events from intimate gatherings of 5 to large receptions of up to 1,000 guests.Whether you're planning a wedding, conference, or corporate meeting, we deliver exceptional service to make your event a success. Guest also enjoy a wide range of amenities designed for comfort and convenience, including free WIFI, Fitness Center and indoor pool, restaurant and bar and on site guest laundry. Whatever brings you to the Berkshires, we look forward to making your stay memorable.
Pool
Free Wi-Fi
7.7
Good
594 reviews
Location
0.5 mi from city centre
445 Pittsfield Road, Lenox, MA, United States
The Hampton Inn & Suites Berkshires Lenox Massachusetts is located just south of Pittsfield, Massachusetts and minutes away from Historic Downtown Lenox, Massachusetts and Tanglewood, summer home of the Boston Symphony Orchestra. Guests will enjoy this prime destination for culture and historic sites: Edith Wharton's The Mount, Naumkeag and Ventfort Hall: recreation: Catamount and Jiminy Peak: art: Norman Rockwell Museum: theatre: The Colonial Theatre, Barrington Stage Company and Shakespeare & Company: world class museums: The Clark, Mass MOCA: dance: Jacob's Pillow and Mahaiwe: and music venues: Tanglewood: just to name a few! The Hampton Inn & Suites Berkshires-Lenox features 79 rooms and suites located in the heart of the culturally rich Berkshire Mountains. Guests will enjoy a welcoming atmosphere as they walk into lobby/seating area with fireplace and large screen television. Whether traveling for business or leisure, you'll find exactly what you need at the Hampton Inn & Suites, Lenox. Along with earning Hilton Honors Points and Miles - you'll enjoy a complimentary On the House hot breakfast daily, exercise room, indoor swimming pool, business center, on-site laundry facilities, complimentary stay for children under 18 accompanied by parents and a meeting facility. Start your day with a complimentary USA Today Monday through Friday and the 100% Hampton Guarantee. Enjoy a relaxing cup of coffee or tea offered 24 hours a day and a fresh cookie at check-in. We love having you here at the Hampton Inn & Suites Berkshires Lenox Massachusetts!
Pool
Free Wi-Fi
Parking
8.7
Excellent
467 reviews
Location
3.2 mi from city centre
203 Main Street, Lenox, MA, United States
Bed & breakfast in Lenox with free breakfast and a 24-hour front desk This smoke-free bed & breakfast features a restaurant, a bar/lounge, and a coffee shop/cafe. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area are onsite. The Cornell Inn, Lenox & The Berkshires offers 28 air-conditioned accommodations with coffee/tea makers and hair dryers. Each accommodation is individually furnished and decorated. Televisions come with cable channels. Bathrooms include showers and complimentary toiletries. This Lenox bed & breakfast provides complimentary wireless Internet access. Housekeeping is provided daily. The recreational activities listed below are available either on site or nearby; fees may apply.
Free Wi-Fi
Parking
9.3
Excellent
641 reviews
Location
0.7 mi from city centre
415 Stockbridge Road, Great Barrington, MA, United States
The Holiday Inn Express Great Barrington provides the perfect home base while visiting the Berkshires. This property offers all the convenience of home, allowing you to keep up with your routines and be as productive as possible. Complimentary Hot Breakfast, 24-hour Fitness Center, Business Center and Market/Sundry Shop offer great convenience and quality throughout your stay. Our hotel is located just minutes from Ski Butternut and Catamount Ski areas with discounted rates available. From daytime and twilight skiing and snowboarding to snowtubing and cross country skiing, the area is a mecca for winter sports enthusiasts. For nearly two decades we have been providing outstanding service for those visiting local boarding schools and colleges such as Simons Rock, Berkshire School, John Dewy Academy, as well as Salisbury School and Hotchkiss School in nearby Connecticut. Whether traveling for business, pleasure or both, the Holiday Inn Express Great Barrington is the place to stay in the Berkshires.
Pool
Free Wi-Fi
Parking
8.4
Excellent
368 reviews
Location
1.5 mi from city centre

Top-rated The Berkshires hotels

Browse through properties in The Berkshires that have received the highest ratings from guests. There are currently 1,374 properties in The Berkshires and data was last updated on August 20, 2025.
According to our users, these are some of the best hotels to stay at in The Berkshires. Skim through hotel descriptions and user reviews to find the right one for you.
20 West Housatonic Street, Pittsfield, MA, United States
0.6 mi from city centre
Free Wi-Fi
Parking
$133
Avg. per night
953 Simonds Road, Williamstown, MA, United States
1.8 mi from city centre
Free Wi-Fi
Parking
$88
Avg. per night
85 Stockbridge Road, Lee, MA, United States
0.8 mi from city centre
Free Wi-Fi
Air Conditioning
$334
Avg. per night
506 Stockbridge Road, Great Barrington, MA, United States
3.4 mi from city centre
Free Wi-Fi
Parking
$171
Avg. per night
555 Main Street, Williamstown, MA, United States
0.6 mi from city centre
Free Wi-Fi
Parking
$140
Avg. per night
247 Stockbridge Road, Great Barrington, MA, United States
1.1 mi from city centre
Free Wi-Fi
Parking
$96
Avg. per night

Cheapest hotels in The Berkshires

Discover affordable stays in The Berkshires that provide a quality experience without breaking the bank. Hotels in The Berkshires can be found for as low as $67 per night. There is currently one property in The Berkshires that can be booked for this price. Pleasant Valley Motel West Stockbridge is one of the hotels that can be booked for the lowest price in The Berkshires. Price data was last updated on August 20, 2025
These are the lowest prices we've found on hotels in The Berkshires at the moment. Prices will typically fluctuate depending on the dates selected, star rating of hotel, and hotel location.
42 Stockbridge Road, West Stockbridge, MA, United States
0.6 mi from city centre
Free Wi-Fi
Parking
$67
Avg. per night
Lee, MA, United States
1.9 mi from city centre
Air Conditioning
$71
Avg. per night
484 Pittsfield Road, Lenox, MA, United States
3.4 mi from city centre
Free Wi-Fi
Parking
$77
Avg. per night
12703 Route 22, Canaan, NY, United States
4.2 mi from city centre
Free Wi-Fi
Parking
$81
Avg. per night
400 Stockbridge Road, Great Barrington, MA, United States
1.5 mi from city centre
Free Wi-Fi
Parking
$84
Avg. per night
284 Sand Springs Rd. Rte 7, Williamstown, MA, United States
1.6 mi from city centre
Free Wi-Fi
Parking
$86
Avg. per night
462 Pittsfield Road, Lenox, MA, United States
3.3 mi from city centre
Free Wi-Fi
Parking
$86
Avg. per night

Hotel prices in The Berkshires

Get a sense of the average price and most popular properties to stay in The Berkshires to help you budget for your trip accordingly. Hotels that are booked the most in each class receive the “Most popular” badge. Hotels with the “Best value” badge are the most popular hotels in The Berkshires at attractive prices. Price data was last updated on August 20, 2025.
An overview of the average price of hotels by hotel class in the The Berkshires. Change the dates at the top of the page to see more options in The Berkshires.
4 stars +
101 Spring Street, Williamstown, MA, United States
615 Laurel Street, Lee, MA, United States
91 Walker Street, Lenox, MA, United States
33 Main Street, Lenox, MA, United States
20 West Housatonic Street, Pittsfield, MA, United States
3 stars
194 Pittsfield Road, Lenox, MA, United States
203 Main Street, Lenox, MA, United States
30 Main Street, Stockbridge, MA, United States
2 stars and under
16 Cheshire Road, Pittsfield, MA, United States
150 West Housatonic Street, Pittsfield, MA, United States
462 Pittsfield Road, Lenox, MA, United States
484 Pittsfield Road, Lenox, MA, United States

Other accommodations in The Berkshires

Find the perfect hostel, theme hotel, or vacation rental for your stay in The Berkshires. There are 1,374 hotels in The Berkshires and price data was last updated on August 20, 2025. The average price for a stay in The Berkshires is .
24 East Ida B. Wells Drive, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$49
Avg. per night
449 Banff Avenue, Banff, AB, Canada
0.5 mi from city centre
Free Wi-Fi
Parking
$34
Avg. per night
Vandkunsten 5, Copenhagen, Capital Region, Denmark
0.7 mi from city centre
Free Wi-Fi
$27
Avg. per night

Where to stay in The Berkshires

Explore different neighborhoods and areas within The Berkshires to find the perfect location for your stay. Map data was last updated on August 20, 2025.
Use the map to find hotels in The Berkshires that are close to the points of interest you'll be frequenting. As an added benefit, users can click a hotel they're interesting in to find helpful information and deals for that hotel.

Facts about staying in The Berkshires

Find useful tips and insights about staying in The Berkshires to help you make the most of your experience. FAQs were last updated on August 20, 2025.
  • Where is the best place to stay in The Berkshires?

    The Berkshires has plenty to offer. Consider staying in some of its favored locations, like Lenox, Pittsfield, and Great Barrington.

  • What are the best hotels in The Berkshires?

    The Yankee, Trademark Collection by Wyndham (8.4/10 from 1,260 reviews), The Red Lion Inn (8.2/10 from 585 reviews), and Holiday Inn Club Vacations Oak n' Spruce Resort (8.8/10 from 570 reviews) are all highly rated places to stay in The Berkshires.

  • What is a good hotel near Tanglewood?

    Apple Tree Inn is a popular hotel near Tanglewood that is highly recommended, with a score of 8.6 across 350 reviews.

  • What is a good hotel in The Berkshires near Williams College?

    The Williams Inn is rated 9.3 from 163 reviews and is close to Williams College.

  • Is there a good hotel near Mass MoCA?

    A good hotel near Mass MoCA is The Porches Inn At Mass Moca, which has been rated 8.6/10 by 228 HotelsCombined user reviews.

  • What are the most popular landmarks to visit in The Berkshires?

    Tanglewood, Williams College, and Mass MoCA are the most popular landmarks in The Berkshires according to our data. You can experience Tanglewood if you plan to visit Lenox. You can visit Williams College if you stay in Williamstown. Mass MoCA is accessible while staying in North Adams.

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