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
The price is HK$1,750 per night from 29 Jul to 30 Jul
HK$1,750
HK$1,955 total
29 Jul - 30 Jul
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! (26 reviews)
Lovely stay
"Brad was a terrific host in a perfect location to explore northwestern Connecticut and the Berkshires."

Reviewed on 16 Jun 2025

Wilder House Berkshires
Antique Farmhouse Totally Restored

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! (56 reviews)
Beautiful farmhouse
"We thoroughly enjoyed our stay and would definitely rent this home again. The house is spacious and well-suited for family time, hosting, or just relaxing. It’s furnished with a lot of historical details and ephemera which was charming and helps make the home a really interesting place to stay. One ..."

Reviewed on 20 Jun 2025

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Antique Farmhouse Totally Restored
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 HK$1,248 per night from 30 Jul to 31 Jul
HK$1,248
HK$1,504 total
30 Jul - 31 Jul
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! (681 reviews)
"I liked the size of the rooms and how comfortable everything in the room was. It was stocked with everything we needed. I did not like the lack of accessibility for people with disabilities. There are elevators, but they are blocked, and there is limited disability parking. I was on the third floor ..."

Reviewed on 24 Jul 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,263 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

The Race Mountain House

2 out of 5
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! (2 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 7 Jul 2025

The Race Mountain House
Antique Farmhouse Totally Restored

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! (56 reviews)
Beautiful farmhouse
"We thoroughly enjoyed our stay and would definitely rent this home again. The house is spacious and well-suited for family time, hosting, or just relaxing. It’s furnished with a lot of historical details and ephemera which was charming and helps make the home a really interesting place to stay. One ..."

Reviewed on 20 Jun 2025

Antique Farmhouse Totally Restored
Guesthouse Cabin vacation rentals in Berkshire County

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! (6 reviews)
"Very nice property. A bit light on household products, bedding."

Reviewed on 4 Jun 2025

Guesthouse Cabin vacation rentals in Berkshire County
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

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

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

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