Name: The Yankee Inn
Price range: $142 total
Rating: 9.2

Wilder House Berkshires

48 S Main Street Sheffield MA

$183 nightly

$205 total

Jun 23 - Jun 24

Total with taxes and fees

Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...

9.8/10 Exceptional! (54 reviews)

"The welcoming spaces still allowed for privacy while providing the most wonderful comforts such as cold and hot drinks, books,board games and a garden retreat. Our room could be kept at our preferred temperature with an individual, quiet cooling unit that didn't block the garden view. The morning ..."

Reviewed on Jun 10, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$155 nightly

$173 total

Jun 21 - Jun 22

Total with taxes and fees

Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...

9/10 Wonderful! (991 reviews)

"Very clean room and kitchen. Sofa needs to be replaced. Staff was excellent! Great location!"

Reviewed on Jun 19, 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

$127 nightly

$142 total

Jun 21 - Jun 22

Total with taxes and fees

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 ...

9.2/10 Wonderful! (1,002 reviews)

"A great hotel to stay in Berkshires. Close to everything we wanted: trails, cafes and restaurants, places of interest. Comfortable room again with everything we need in it. Amazing complex of in and outdoors pools, exercise room, hot tub, a decent breakfast. And an uncomparable per night price."

Reviewed on Jun 19, 2026

See all 1,276 properties in Sheffield

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.

The Race Mountain House

Sheffield MA

Stay at this vacation home in Sheffield. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Mount Everett State Reservation and Drury ...

9.6/10 Exceptional! (7 reviews)

"We had a wonderful 2-day stay at this charming house! The location is perfect, nestled near the mountains with breathtaking views. The house itself is clean and cozy, with comfortable bedrooms stocked with extra blankets and pillows. The spacious bathrooms (both upstairs and downstairs!) had plenty ..."

Reviewed on Jan 3, 2026

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield MA

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! (10 reviews)

"We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ..."

Reviewed on Jan 29, 2026

Antique Farmhouse Totally Restored

Sheffield MA

Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Mount Riga State Park and ...

9.8/10 Exceptional! (98 reviews)

"This is our third visit to the farmhouse in Sheffield and we plan to be back again if it’s available. The house has everything you could possibly need or want with lots of space and an outstanding fully equipped kitchen Robin, our host makes it easy for us to wanna come back."

Reviewed on Jun 2, 2026

See all properties in Sheffield

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.

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Popular places to visit

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.

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.

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.

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.

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.