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Featured The Berkshires Family Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Stay Berkshires
1146 Cold Spring Road Williamstown MA
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Margaret Lindley Park and Lindley Park are located ...
Williamstown Motel
295 Main Street Williamstown MA
Book a stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Cozy Corner Motel
284 Sand Springs Rd. Rte 7 Williamstown MA
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Econo Lodge Lee - Great Barrington
980 Pleasant Street Lee MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly motel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Book a stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
Lantern House Motel
256 Stockbridge Road Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Pleasant Valley Motel West Stockbridge
42 Stockbridge Rd West Stockbridge MA
Fully refundableReserve now, pay when you stay
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
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.
Hotels with Pools in The Berkshires
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,010 reviews)
All of the above!
Reviewed on Jan 3, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,195 reviews)
No frills stay with a kitchen and dishwasher (make sure your room has one— some do not!!!). Location is across the street from Jiminy Peak, so skiing can be accomplished almost as easy as staying on their property. This is our fourth time staying and it always serves its purpose.
Reviewed on Dec 30, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,004 reviews)
Staff was very pleasant and friendly. From front desk to valet.
Reviewed on Jan 1, 2026
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.
Hotels With Connecting Rooms in The Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
Chestnut Lodge
75 Chestnut Street Lee MA
Stay at this guesthouse in Lee. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Goose Pond Reservation and Lee Premium Outlets are located ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
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.
Hotels by Star Rating
More Hotel Options
- Hotels with Free Parking in The Berkshires
- Historic Hotels in The Berkshires
- Hotels with a Pool in The Berkshires
- Luxury Hotels in The Berkshires
- Resorts & Hotels with Spas in The Berkshires
- Romantic Hotels in The Berkshires
- Pet-friendly Hotels in The Berkshires
- Hotels with Hot Tubs in The Berkshires
- Winery Hotels in The Berkshires
- Apartment Hotel in The Berkshires
Top Points of Interests in The Berkshires
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Tanglewood Music Center
- Hotels near Ski Butternut
- Hotels near National Shrine of the Divine Mercy
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Williams College
- Hotels near Bousquet Ski Area
- Hotels near The Clark Art Institute
- Hotels near Mount Greylock
- Hotels near Lee Premium Outlets
- Hotels near Norman Rockwell Museum
- Hotels near Jacob's Pillow
- Hotels near The Mount
- Hotels near Naumkeag Museum
- Hotels near Colonial Theater
- Hotels near Mahaiwe Performing Arts Center
- Hotels near Williamstown Theatre Festival
- Hotels near Housatonic River Walk
- Hotels near Housatonic River
- Hotels near Wyndhurst Golf & Club
Cities near The Berkshires
- Hudson Hotels (33.34 mi)
- Upstate New York Hotels (141.08 mi)
- The Catskills Hotels (73.95 mi)
- West Dover Hotels (55.42 mi)
- Lenox Hotels (14.84 mi)
- Williamstown Hotels (37.75 mi)
- Rhinebeck Hotels (42.49 mi)
- Great Barrington Hotels (11.05 mi)
- Brattleboro Hotels (56.08 mi)
- Pittsfield Hotels (20.16 mi)
- Northampton Hotels (28.19 mi)
- Hudson Valley Hotels (58.11 mi)
- Windsor Hotels (33.83 mi)
- Troy Hotels (47.61 mi)
- Stockbridge Hotels (12.08 mi)
- Wilmington Hotels (50.48 mi)
- West Springfield Hotels (27.39 mi)
- Hancock Hotels (27.16 mi)
- Litchfield Hotels (29.04 mi)
- Lee Hotels (10.74 mi)