Book Hotels in The Berkshires, MA

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Check hotel availability in The Berkshires

Tonight
Check prices in The Berkshires for tonight, May 29 - May 30
May 29 - May 30
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May 30 - May 31
Next weekend
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Jun 3 - Jun 5

Most frequently booked The Berkshires hotels

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA, 01201
Free Cancellation
5.67 mi from city center
The price is $117 per night
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 10 conference rooms, as well as the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Free WiFi
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Hancock, MA, 01237
Free Cancellation
Reserve now, pay when you stay
13.56 mi from city center
The price is $169 per night
This condo features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. A business center, a terrace, and a garden are also on offer.
Pool
Free WiFi
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA, 01238
Free Cancellation
Reserve now, pay when you stay
4.49 mi from city center
The price is $116 per night
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a picnic area, and laundry facilities are also on offer.
Free WiFi
Breakfast included
Yankee Inn

Yankee Inn

2.5 out of 5
461 Pittsfield Rd, Lenox, MA, 01240
Free Cancellation
Reserve now, pay when you stay
3.51 mi from city center
The price is $94 per night
A full-service spa and an indoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Free WiFi
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA, 01262
Free Cancellation
Reserve now, pay when you stay
8.26 mi from city center
The price is $203 per night
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Free WiFi
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

3.5 out of 5
190 Meadow Street, South Lee, MA, 01260
Free Cancellation
7.67 mi from city center
The price is $149 per night
This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 indoor pools. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Unwind with drinks at one of the 2 bars/lounges or the poolside bar and make the most of the 2 outdoor tennis courts.
Pool
Air conditioning
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA, 01201
Free Cancellation
Reserve now, pay when you stay
6.73 mi from city center
The price is $129 per night
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and laundry facilities and free newspapers are also offered.
Free WiFi
Parking included
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3 out of 5
1032 South Street, Pittsfield, MA, 01201
Free Cancellation
Reserve now, pay when you stay
3.69 mi from city center
The price is $164 per night
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Free WiFi
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA, 01201
Free Cancellation
Reserve now, pay when you stay
5.52 mi from city center
The price is $80 per night
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is provided and the front desk is staffed around-the-clock.
Pool
Free WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top family friendly The Berkshires hotel deals

  • Econo Lodge Lee - Great Barrington

    Econo Lodge Lee - Great Barrington

    980 Pleasant Street, Lee, MA, 01238
    The price is $55 per night from Jun 12 to Jun 13
    2.3/5 (10 reviews)
    Econo Lodge Lee - Great Barrington
  • Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Hancock, MA, 01237
    The price is $169 per night from May 30 to May 31
    4/5 Very Good! (34 reviews)
    Vacation Village in the Berkshires
  • Holiday Inn Berkshires, an IHG Hotel

    Holiday Inn Berkshires, an IHG Hotel

    40 Main St, North Adams, MA, 01247
    Get rates
    3.1/5 (12 reviews)
    Holiday Inn Berkshires, an IHG Hotel
  • Stay Berkshires - A Country Inn

    Stay Berkshires - A Country Inn

    1146 Cold Spring Road, Williamstown, MA, 01267
    The price is $185 per night from May 30 to May 31
    4.8/5 Exceptional! (5 reviews)
    Stay Berkshires - A Country Inn
  • Williamstown Motel

    Williamstown Motel

    295 Main Street, Route 2, Williamstown, MA, 01267
    The price is $99 per night from May 31 to Jun 1
    3.8/5 Good! (12 reviews)
    Williamstown Motel
  • Cozy Corner Motel

    Cozy Corner Motel

    284 Sand Springs Rd. Rte 7, Williamstown, MA, 01247
    The price is $77 per night from May 31 to Jun 1
    4.2/5 Excellent! (17 reviews)
    Cozy Corner Motel

Top cheap The Berkshires hotel deals

  • Wagon Wheel Inn

    Wagon Wheel Inn

    484 Pittsfield Rd, PO Box 808, Lenox, MA, 01240
    The price is $69 per night from May 30 to May 31
    3.3/5 (11 reviews)
    Wagon Wheel Inn
  • Pleasant Valley Motel West Stockbridge

    Pleasant Valley Motel West Stockbridge

    42 Stockbridge Rd, West Stockbridge, MA, 01266
    The price is $79 per night from May 30 to May 31
    3/5 (14 reviews)
    Pleasant Valley Motel West Stockbridge
  • Lantern House Motel

    Lantern House Motel

    256 Stockbridge Road, Great Barrington, MA, 01230
    Get rates
    4.3/5 Excellent! (22 reviews)
    Lantern House Motel
  • The Weathervane Motel

    The Weathervane Motel

    475 South Main St. Route 7, Lanesborough, MA, 01237
    Get rates
    5/5 Exceptional! (2 reviews)
    The Weathervane Motel
  • Howard Johnson by Wyndham Lenox

    Howard Johnson by Wyndham Lenox

    462 Pittsfield Rd, Routes 7 and 20, Lenox, MA, 01240
    The price is $79 per night from Jun 5 to Jun 6
    3.9/5 Good! (17 reviews)
    Howard Johnson by Wyndham Lenox
  • Monument Mountain Motel

    Monument Mountain Motel

    247 Stockbridge Rd, Great Barrington, MA, 01230
    The price is $80 per night from May 30 to May 31
    4.6/5 Exceptional! (13 reviews)
    Monument Mountain Motel

Top hotels in The Berkshires for Extended Stay

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Hancock, MA
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Seize your some day

The Berkshires Hotel & Travel Guide

Are you on the hunt for a getaway that's truly away from it all? You can't go wrong with a trip to The Berkshires. With its abundance of lush forests, gently sloping hills, and cultural amenities, you'll be hard pressed to find a lovelier place. Choose from among many daily Albany flights to get there in no time, and get ready to explore all of Massachusetts' most magnificent wonders.

Out and About in The Berkshires

Start your tour of The Berkshires by enjoying the gorgeous scenery. To get the best views, climb Mount Greylock. If you can make it to the top, then congratulations! You'll be at the highest point in all of Massachusetts—take in breathtaking views of the dramatic landscape. After your trek, see fascinating exhibits at the Massachusetts Museum of Contemporary Art (MOCA). If art galleries aren't your thing, then be sure to stop by MoCA to check out the live events. Whether you're into theater, musical performance, or films, you're sure to find something you'll enjoy. Afterwards, head back to your The Berkshires hotel to unwind.

Eating and Drinking

Feeling a bit famished? Go to Great Barrington to find the highest concentration of great restaurants in The Berkshires. You'll find that most menus place an emphasis on serving up classic American comfort food. Go ahead and pig out on a burger and fries or some fresh lobster. If you're looking for the hippest bars, stick around Great Barrington. The bars here are cozy and small but offer innovative cocktails in an inviting atmosphere. Be sure to try out a frozen whisky lemonade. They're absolutely delicious. After a great night, rest up at any of the charming hotels in The Berkshires.

Ready to relax in style at the best hotels in The Berkshires? Thanks to Travelocity, it's never been easier to book your ideal getaway. You can search more than 510,000 hotels and 400 airlines to find the perfect vacation package to The Berkshires. You're sure to be enchanted on your holiday to rural Massachusetts.

Recent The Berkshires hotel reviews by fellow wanderers

  • Yankee Inn

    Yankee Inn

    5 out of 5
    Posted 3 weeks ago
    travelocity Verified Review
    "I liked staying here and I will gladly stay again!"
    A verified traveler stayed at Yankee Inn
    Yankee Inn
  • The Villager Motel

    The Villager Motel

    5 out of 5
    Posted 2 months ago
    travelocity Verified Review
    "nice people very clean "
    A verified traveler stayed at The Villager Motel
    The Villager Motel
  • Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

    Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

    5 out of 5
    Posted 3 months ago
    travelocity Verified Review
    "The staff was very accommodating. We needed a microwave so they sent someone up. The garage was closed so the provided free valet service. The only problem was the hot tub was broken and the pool was so cloudy you could not see the bottom. This is a serious safety issue. Otherwise everything about the place was great!"
    A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
    Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires

    1 out of 5
    Posted 4 months ago
    travelocity Verified Review
    "Booked 2 BdRm suite , old furnishings, dirty, noisy and DISRESPECTFUL staff with non existent management, 5 Black streaks across bedroom mirrored wall make up or sharpie , stove burners non function,odd smell permeated the room, appartently maid dumped liquid cover up all over room carpets, Sunday Night asked to move room , nothing was done , Really $200 bucks a night, asked to speak Manager Cindy , would not answer calls, BEWARE of this place"
    A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
  • Hilton Garden Inn Lenox Pittsfield

    Hilton Garden Inn Lenox Pittsfield

    5 out of 5
    Posted 6 months ago
    travelocity Verified Review
    "From the minute we walked in we were impressed with the cleanliness of the hotel. Front desk staff was super friendly and our room was very clean and cozy."
    A verified traveler stayed at Hilton Garden Inn Lenox Pittsfield
    Hilton Garden Inn Lenox Pittsfield
  • The Red Lion Inn

    The Red Lion Inn

    5 out of 5
    Posted 7 months ago
    travelocity Verified Review
    "The room was very comfortable and well equipped-quiet and restful. Lovely furnishings, the bathroom excellent."
    A verified traveler stayed at The Red Lion Inn
    The Red Lion Inn