Sheffield

Travel Guide

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA
Sheffield
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
The price is €153 per night from 14 Apr to 15 Apr
€153
14 Apr - 15 Apr
includes taxes & fees
Stay at this B&B in Sheffield. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
9.8/10 Exceptional! (44 reviews)
Only discomfort was a hard rug on my barefeet. So I'll remember to bring slippers. Otherwise, the ambiance, service, friendliness, access was wonderful. What a lovely place!

Reviewed on 3 Apr 2026

Wilder House Berkshires
Luxury Private Estate in the Berkshires | Whitney by AvantStay

Luxury Private Estate in the Berkshires | Whitney by AvantStay

Sheffield MA
Stay at this family-friendly holiday home in Sheffield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Thom Reed UFO Monument Park and ...
8.6/10 Excellent! (15 reviews)
We had a lovely stay. Wonderfully located and well provisioned! Would happily stay here again!

Reviewed on 29 Mar 2026

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Luxury Private Estate in the Berkshires | Whitney by AvantStay
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is €102 per night from 12 May to 13 May
€102
12 May - 13 May
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (901 reviews)
Yes everything was very geared for a enjoyable time.

Reviewed on 11 Apr 2026

Berkshire Mountain Lodge
See all 1,302 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.
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
Stay at this family-friendly holiday home in Sheffield. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Mount Riga State Park and Taconic ...
Antique Farmhouse Totally Restored
Luxury Private Estate in the Berkshires | Whitney by AvantStay

Luxury Private Estate in the Berkshires | Whitney by AvantStay

Sheffield MA
Stay at this family-friendly holiday home in Sheffield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Thom Reed UFO Monument Park and ...
8.6/10 Excellent! (15 reviews)
We had a lovely stay. Wonderfully located and well provisioned! Would happily stay here again!

Reviewed on 29 Mar 2026

Luxury Private Estate in the Berkshires | Whitney by AvantStay
The Race Mountain House

The Race Mountain House

Sheffield MA
Stay at this holiday 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 3 Jan 2026

The Race Mountain House
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.

Popular places to visit

Magnolia Bluffs Casino

Why not roll the dice with a visit to Magnolia Bluffs Casino during your time in Sheffield? Discover the area's breweries or seek out the hiking trails.

Magnolia Bluffs Casino

Ashley House

You can learn about the history of Sheffield when you stop by Ashley House. Discover the area's breweries or seek out the hiking trails.

Ashley House

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.

Drury Preserve

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.

Lime Kiln Farm Wildlife Sanctuary

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.

Bartholomew's Cobble

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.

Bartholomews Cobble
Great Barrington

Great Barrington