Find Pet-friendly Hotels in Sheffield, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sheffield Pet-friendly Hotels

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Sheffield Pet-friendly Hotels

Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is NT$3,433
NT$3,835 total
includes taxes & fees
Dec 10 - Dec 11
Berkshires Untold
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is NT$3,168
NT$3,539 total
includes taxes & fees
Dec 14 - Dec 15
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is NT$3,413
NT$3,744 total
includes taxes & fees
Dec 10 - Dec 11
Shaker Mill Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is NT$3,231
NT$3,609 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn & Suites Berkshires-Lenox
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is NT$4,040
NT$5,912 total
includes taxes & fees
Jan 4 - 2026/1/5
The Red Lion Inn
Dinner served, American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (185)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is NT$4,383
NT$4,909 total
includes taxes & fees
Dec 8 - Dec 9
the Alander
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is NT$2,348
NT$2,623 total
includes taxes & fees
Dec 10 - Dec 11
Travelodge by Wyndham Great Barrington Berkshires
Porch
Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging

3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
"Great experience, looking forward to staying again."
United States
Greg
The price is NT$4,696
NT$5,260 total
includes taxes & fees
Dec 7 - Dec 8
Changing Times Boutique Country Lodging
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is NT$3,444
NT$3,847 total
includes taxes & fees
Jan 1 - 2026/1/2
The Little Lion
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (88)
"Outstanding all around!"
United States
Jonathan
The price is NT$6,262
NT$6,994 total
includes taxes & fees
Jan 1 - 2026/1/2
Granville House
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.
View all properties

Top Sheffield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"I love the ambience - historic and comfortable and excellent food. "
Nancy 1-night trip
Posted 1 month ago
The Red Lion Inn
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"Super friendly and pet friendly. We are so grateful to have been able to check in early to finish getting ready for the wedding we attended! Thank you for the hospitality! "
Heather 1-night trip
Posted 2 months ago
Interlaken Inn & Resort

Explore a world of travel with Expedia

Frequently asked questions

What's the best time of year to travel to Sheffield with my pet?
When you're traveling with pets, keeping track of the weather can help you make the trip more safe and fun for everyone. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to see and do with your pet in Sheffield?
Known for its casinos, Sheffield has lots to offer visitors. See the local sights and visit Housatonic River and Magnolia Bluffs Casino. While you're there, make sure you don't miss Three Mile Pond Wildlife Management Area and Mount Everett State Reservation.