Sheffield, MA
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
$180 nightly
The price is $201 total per night from May 7 to May 8
$201 total
May 7 - May 8
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! (46 reviews)
Loved everything!
Reviewed on Apr 27, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from May 24 to May 25
$126 total
May 24 - May 25
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! (924 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on May 4, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
$92 nightly
The price is $103 total per night from May 7 to May 8
$103 total
May 7 - May 8
Total with taxes and fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (931 reviews)
Such a lovely and nicely furnished hotel. It has a very hip and earthy vibe and you can see a lot of care has been put into this property. This staff were helpful and friendly. Lenox is a pretty town with good restaurants and stunning historic architecture.
Reviewed on May 6, 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.
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Sheffield MA
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thom Reed UFO Monument ...
8.6/10 Excellent! (15 reviews)
We had a lovely stay. Wonderfully located and well provisioned! Would happily stay here again!
Reviewed on Mar 29, 2026
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
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 ...
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.
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.
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.
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.
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- Magnolia Bluffs Casino
- Tanglewood Music Center
- National Shrine of the Divine Mercy
- Norman Rockwell Museum
- Lime Rock Park
- The Mount
- Jacob's Pillow
- Mohawk Mountain Ski Area
- Lee Premium Outlets
- Ski Butternut
- Kent Falls State Park
- Naumkeag Museum
- Berkshire Botanical Garden
- Catamount Aerial Adventure Park
- Catamount Ski Area
- Mohawk Mountain State Forest
- Mahaiwe Performing Arts Center
- Bousquet Ski Area
- Housatonic River Walk
- Taconic State Park
- Goose Pond Reservation
- Otis Reservoir
- Infinity Music Hall and Bistro
