Visit Sheffield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
Reviewed on Aug 23, 2025
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
$160 nightly
The price is $179 total per night from Aug 25 to Aug 26
$179 total
Aug 25 - Aug 26
Total with taxes and fees
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (693 reviews)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise"
Reviewed on Aug 21, 2025
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Sep 7 to Sep 8
$104 total
Sep 7 - Sep 8
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
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.
Antique Farmhouse Totally Restored
Sheffield
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park ...
9.8/10 Exceptional! (57 reviews)
"The property was beautiful. Very spacious, inside and out."
Reviewed on Aug 17, 2025
The Race Mountain House
Sheffield
Stay at this vacation home in Sheffield. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Mount Everett State Reservation and Drury ...
10/10 Exceptional! (3 reviews)
Extended family getaway
"This trip was for our extended family including 10 people ages 18-??. This house is located about 1/2 mile up a windy road above the race brook lodge's main facilities. Everyone loved the secluded location with beautiful views of the mountains out of main living area and 2nd floor. There were so ..."
Reviewed on Jul 7, 2025
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond ...
10/10 Exceptional! (7 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space."
Reviewed on Aug 12, 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.
Popular places to visit
Magnolia Bluffs Casino
Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails.
Ashley House
You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.
Bartholomew's Cobble
You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Lime Kiln Farm Wildlife Sanctuary
You can take time to visit Lime Kiln Farm Wildlife Sanctuary during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Drury Preserve
You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Bartholomews Cobble
Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.
Explore a world of travel with Expedia
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- Magnolia Bluffs Casino
- Tanglewood Music Center
- National Shrine of the Divine Mercy
- Catamount Ski Area
- Lime Rock Park
- Mohawk Mountain Ski Area
- Norman Rockwell Museum
- Ski Butternut
- Lee Premium Outlets
- Jacob's Pillow
- The Mount
- Kent Falls State Park
- Bousquet Ski Area
- Taconic State Park
- Catamount Aerial Adventure Park
- Naumkeag Museum
- Lake Taghkanic State Park
- West Cornwall Covered Bridge
- Ventfort Hall Mansion and Gilded Age Museum
- Berkshire Botanical Garden
- Mohawk Mountain State Forest
- Mahaiwe Performing Arts Center
- Otis Reservoir
- Infinity Music Hall and Bistro
- Housatonic River Walk