Hotels in The Berkshires
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Popular hotels in The Berkshires
Discover well-known properties in The Berkshires that are favoured by visitors more than others. There are 1,059 hotels in The Berkshires and price data was last updated on 8 October 2026. The average price for a hotel in The Berkshires is .
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All filters461 Pittsfield Road, Lenox, MA, United States
Along with an indoor pool, this smoke-free hotel has an outdoor pool and a 24-hour fitness center. Free buffet breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a bar/lounge, a hot tub, and coffee/tea in a common area.
Pool
Free Wi-Fi
Parking
8.5
Excellent
1404 reviews
Location
5.4 km from city centre
S$ 132
30 Main Street, Stockbridge, MA, United States
This smoke-free hotel features 3 restaurants, an outdoor pool, and a fitness center. Free WiFi in public areas and free self parking are also provided. Other amenities include a bar/lounge, a 24-hour business center, and coffee/tea in a common area.
Free Wi-Fi
Parking
8.2
Excellent
649 reviews
Location
1.0 km from city centre
S$ 269
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.
Pool
Free Wi-Fi
Parking
8.8
Excellent
722 reviews
Location
3.9 km from city centre
S$ 143
1 West Street, Pittsfield, MA, United States
Settle in and experience the best of the Berkshires at Holiday Inn & Suites Pittsfield. Perfectly located in the heart of the region, our hotel puts you close to mountain views, scenic trails, and local culture. Catch a show at the Colonial Theatre or Barrington Stage, spend a summer evening at Tanglewood, or explore outdoor adventures like hiking the Appalachian Trail and skiing at Jiminy Peak.
Pool
Free Wi-Fi
7.2
Good
639 reviews
Location
0.8 km from city centre
S$ 132
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.
Pool
Free Wi-Fi
Parking
8.4
Excellent
506 reviews
Location
5.2 km from city centre
S$ 154
276 Brodie Mountain Road, Hancock, MA, United States
Along with an indoor pool, this smoke-free aparthotel has an outdoor pool and a fitness center. Free WiFi in public areas and free self parking are also provided. Additionally, a business center, a children's pool, and concierge services are onsite.
Pool
Parking
8.6
Excellent
1269 reviews
Location
3.7 km from city centre
S$ 115
Top-rated The Berkshires hotels
Browse through properties in The Berkshires that have received the highest ratings from guests. There are currently 1,059 properties in The Berkshires and data was last updated on 8 October 2026.
Our users rated these hotels as some of the best places to stay in The Berkshires. Make sure to read hotel descriptions and reviews to find the right property right for you.
20 West Housatonic Street, Pittsfield, MA, United States
1.0 km from city centre
Free Wi-Fi
Parking
S$ 141
Avg. per night
953 Simonds Road, Williamstown, MA, United States
2.8 km from city centre
Free Wi-Fi
Air conditioning
S$ 100
Avg. per night
85 Stockbridge Road, Lee, MA, United States
1.3 km from city centre
Free Wi-Fi
Air conditioning
S$ 527
Avg. per night
506 Stockbridge Road, Great Barrington, MA, United States
5.4 km from city centre
Free Wi-Fi
Parking
S$ 138
Avg. per night
555 Main Street, Williamstown, MA, United States
1.0 km from city centre
Free Wi-Fi
Parking
S$ 142
Avg. per night
910 Cold Spring Road, Williamstown, MA, United States
2.7 km from city centre
Free Wi-Fi
Air conditioning
S$ 124
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 S$ 52 per night. There is currently one property in The Berkshires that can be booked for this price. Fairbridge Inn Express Pittsfield is one of the hotels that can be booked for the lowest price in The Berkshires. Price data was last updated on 8 October 2026
Out of the hotels in The Berkshires we've come across, these properties are priced the lowest. Consider alternative dates if you're able to compare prices.
16 Cheshire Road, Pittsfield, MA, United States
4.1 km from city centre
Free Wi-Fi
Parking
S$ 52
Avg. per night
42 Stockbridge Road, West Stockbridge, MA, United States
1.0 km from city centre
Free Wi-Fi
Air conditioning
S$ 78
Avg. per night
12703 Route 22, Canaan, NY, United States
6.8 km from city centre
Free Wi-Fi
Parking
S$ 86
Avg. per night
S$ 87
Avg. per night
99 Howland Avenue, Adams, MA, United States
2.9 km from city centre
Free Wi-Fi
Air conditioning
S$ 87
Avg. per night
247 Stockbridge Road, Great Barrington, MA, United States
1.8 km from city centre
Free Wi-Fi
Parking
S$ 95
Avg. per night
165 Housatonic Street, Lee, MA, United States
0.6 km from city centre
Free Wi-Fi
Air conditioning
S$ 96
Avg. per night
462 Pittsfield Road, Lenox, MA, United States
5.4 km from city centre
Parking
S$ 97
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 8 October 2026.
Some of the best options for booking a hotel in The Berkshires categorized by hotel class. We've highlighted the most popular properties according to our users as well as the best value within each hotel class.
3 stars
190 Meadow Street, Lee, MA, United States
S$ 143
2 stars and under
213 Main Street, Williamstown, MA, United States
S$ 137
Where to stay in The Berkshires
Explore different neighbourhoods and areas within The Berkshires to find the perfect location for your stay. Map data was last updated on 8 October 2026.
Whether you're visiting The Berkshires for leisure or business, utilize the map to find hotels close to your ideal location. Clicking on a hotel name will take you to a page with pricing, reviews, and more useful information.
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 8 October 2026.
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