Sheffield

Travel Guide

Sheffield
Photo by Kim Knox Beckius
Photo by Kim Knox Beckius
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
Fully refundableReserve now, pay when you stay
The price is P10,000 per night from Oct 30 to Oct 31
P10,000
P11,170 total
Oct 30 - Oct 31
includes taxes & 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 ...
9.6/10 Exceptional! (35 reviews)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."

Reviewed on Sep 25, 2025

Wilder House Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is P5,394 per night from Nov 2 to Nov 3
P5,394
P7,318 total
Nov 2 - Nov 3
includes taxes & 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! (662 reviews)
"Very convenient set up of both room and kitchen, resort very easy to navigate."

Reviewed on Sep 28, 2025

Berkshire Mountain Lodge
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
The price is P6,719 per night from Nov 2 to Nov 3
P6,719
P8,313 total
Nov 2 - Nov 3
includes taxes & 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! (739 reviews)
Beautiful in the Berkshires
"Beautiful well-maintained property. Very clean every possible convenient you could want. Friendly welcoming staff plan to return to this property often."

Reviewed on Sep 28, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,258 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 Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (131 reviews)
"Was a nice place to stay"

Reviewed on Sep 26, 2025

The Ponds at Foxhollow
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 travels 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 with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.

Ashley House

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

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

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

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