Visit Colebrook
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Sep 8 to Sep 9
$104 total
Sep 8 - Sep 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,002 reviews)
"Great location and close enough to walk to shops and restaurants."
Reviewed on Aug 22, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
$104 nightly
The price is $116 total per night from Sep 2 to Sep 3
$116 total
Sep 2 - Sep 3
Total with taxes and fees
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (708 reviews)
Berkshire stay good for kids
"If you have kids it’s a great place. Close to Tanglewood. The condo is dated and dark, but convenient."
Reviewed on Aug 25, 2025
Simsbury 1820 House
731 Hopmeadow St, Simsbury, CT
$184 nightly
The price is $212 total per night from Aug 27 to Aug 28
$212 total
Aug 27 - Aug 28
Total with taxes and fees
Book a stay at this business-friendly B&B in Simsbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (981 reviews)
"Sheryl and other staff at the Simsbury 1820 House were so accommodating and helpful. Will definitely come back and highly recommend this property."
Reviewed on Aug 24, 2025
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.
Peace and quiet on the lake
Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (216 reviews)
Lake House Getaway with Access to Berkshire Highlights
"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any ..."
Reviewed on Jul 31, 2025
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Becket
Stay at this cabin in Becket. Enjoy a garden, laundry facilities, and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (188 reviews)
"Great. It was peaceful and relaxing. Had everything you needed. Very nice place in a beautiful location. Wonderful screen porch. We loved everything about it."
Reviewed on Aug 16, 2025
Summer Lake Cottage, private beach, Berkshire Hills, small village
Lakeville
Stay at this cottage in Lakeville. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Holley-Williams House Museum and Harney and Sons Tea Tasting ...
9.4/10 Exceptional! (75 reviews)
"The house is very comfortable and perfect for visiting with family and friends.We enjoyed the roomy kitchen space. The porch is great for relaxing and gazing at the tranquil lake. We appreciated the use of the canoe and the dock."
Reviewed on Jul 20, 2025
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.
- Lime Rock Park
- Mohawk Mountain Ski Area
- Ski Butternut
- Lee Premium Outlets
- Jacob's Pillow
- Warner Theater
- Taconic State Park
- Talcott Mountain State Park
- West Cornwall Covered Bridge
- Mohawk Mountain State Forest
- Mahaiwe Performing Arts Center
- Litchfield Town Green
- Otis Reservoir
- Infinity Music Hall and Bistro
- Housatonic River Walk
- Connecticut Valley Winery
- Ski Sundown
- Goose Pond Reservation
- Music Mountain
- Mount Frissell
- Burr Pond State Park
- Lake Mansfield Park
- Pyramid Lake
- Performing Arts Center at Simsbury Meadows