Search for Cheap Deals onHotels with Pools in The Berkshires
Check Last Minute The Berkshires Hotel Deals
You choose what matters — star rating, location, amenities.
We pick the perfect hotel, packed with all your must-haves.
Your hotel is revealed right after booking!
Featured The Berkshires Hotels with a Pool
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 ...
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 ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West 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 breakfast (surcharge). Our guests praise the helpful staff and ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
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 ...
Berkshire Valley Inn
2541 Hancock Rd Williamstown MA
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Club Wyndham Bentley Brook
1 Corey Road Hancock MA
Book a stay at this ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition ...
Berkshire Inn
150 W Housatonic St Pittsfield MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 ...
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 Porches Inn at Mass MoCA
231 River Street North Adams MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 in The Berkshires
- Hotels with Free Parking in The Berkshires
- Historic Hotels in The Berkshires
- Family Hotels 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 Norman Rockwell Museum
- Hotels near Lee Premium Outlets
- Hotels near The Mount
- Hotels near Jacob's Pillow
- Hotels near Naumkeag Museum
- Hotels near Colonial Theater
- Hotels near Mahaiwe Performing Arts Center
- Hotels near Hancock Shaker Village
- Hotels near Williamstown Theatre Festival
- Hotels near Mount Greylock State Reservation Visitor Center
- Hotels near Housatonic River
Cities near The Berkshires
- Upstate New York Hotels (141.08 mi)
- The Catskills Hotels (73.95 mi)
- West Dover Hotels (55.42 mi)
- Hudson Hotels (33.34 mi)
- Lenox Hotels (14.84 mi)
- Williamstown Hotels (37.75 mi)
- Rhinebeck Hotels (42.49 mi)
- Great Barrington Hotels (11.05 mi)
- Northampton Hotels (28.19 mi)
- Pittsfield Hotels (20.16 mi)
- Brattleboro Hotels (56.08 mi)
- Hudson Valley Hotels (58.11 mi)
- Windsor Hotels (33.83 mi)
- Troy Hotels (47.61 mi)
- Stockbridge Hotels (12.08 mi)
- West Springfield Hotels (27.39 mi)
- Wilmington Hotels (50.48 mi)
- Litchfield Hotels (29.04 mi)
- Holyoke Hotels (26.17 mi)
- Hancock Hotels (27.16 mi)
Most Booked Hotels in The Berkshires
- Hotel Downstreet, an Ascend Collection Hotel
- The Yankee, Trademark Collection by Wyndham
- The Red Lion Inn
- Berkshire Mountain Lodge
- Best Western Plus Berkshire Hills Inn & Suites
- Courtyard by Marriott Lenox Berkshires
- The Porches Inn at Mass MoCA
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- Hampton Inn & Suites Berkshires-Lenox
- Howard Johnson by Wyndham Lenox