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Check availability on Sheffield Pet-Friendly Hotels

Our top choices for Sheffield pet-friendly hotels

Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is ₹11,775
₹13,152 total
includes taxes & fees
17 Dec - 18 Dec
Element Lenox Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is ₹9,709
₹10,650 total
includes taxes & fees
14 Dec - 15 Dec
Shaker Mill Inn
American cuisine
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (188)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is ₹12,584
₹14,094 total
includes taxes & fees
15 Dec - 16 Dec
the Alander
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"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 ₹9,104
₹10,169 total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion

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 ₹9,887
₹11,044 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Little Lion
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (813)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is ₹9,855
₹11,009 total
includes taxes & fees
16 Dec - 17 Dec
Berkshires Untold
Porch
Changing Times Boutique Country Lodging

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 ₹13,483
₹15,100 total
includes taxes & fees
11 Jan - 12 Jan 2026
Changing Times Boutique Country Lodging
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

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 ₹6,741
₹7,530 total
includes taxes & fees
16 Dec - 17 Dec
Travelodge by Wyndham Great Barrington Berkshires
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.
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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

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Frequently asked questions

What's the best time of year to travel to Sheffield with my pet?
When you're travelling 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm 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 Ashley House.