Find Pet-friendly Hotels in Sheffield, MA

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Pick from 14 Sheffield Pet-friendly Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (32)
"We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina is a great host and responded within minutes to any questions I had. We HIGHLY recommend this home."
The price is SAR 890
SAR 1,897 total
includes taxes & fees
5 Jan - 6 January 2025
Cheerful 3-bedroom cottage with woodstove

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

9.8 out of 10, Exceptional, (35)
"We had an incredible time at this beautiful property . Completed secluded , we were in our own private oasis . We had our small intimate wedding on the property , overlooking the water , and it was perfect . The house is clean and cozy . The layout of the house is really nice , and even with many people staying there you aren’t on top of each other . So many things to do outdoors here , we spent the majority of our time enjoying the outdoors , and you really feel like you’re on your own private...
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is SAR 1,973
SAR 3,358 total
includes taxes & fees
8 Jan - 9 January 2025
Guesthouse Cabin vacation rentals in Berkshire County

Whitney by AvantStay | Private Berkshires Estate

8.0 out of 10, Very Good, (11)
"Overall the property was really good. There were a few things broken in the kitchen (fridge ran way too cold, oven ran way too hot, crisper drawers in fridge broken, top dishwasher rack broken) - but we learned to work with them. We had 9 people and we cooked a lot, including Thanksgiving dinner! Upstairs shower in clawfoot tub kind of sprayed water everywhere, leaving the bathroom soaked so we gave up and only used the shower on the first floor - kind of annoying for 9 people. And there were...
Whitney by AvantStay | Private Berkshires Estate

Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!

9.6 out of 10, Exceptional, (5)
"Property was clean and the location was great. I highly recommend"
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!

Little House in the Woods by Evergreen Home

10.0 out of 10, Exceptional, (33)
"We stayed at this property for almost a week and found it to be clean, quiet and very close to my stepdaughter's home in Ashley Falls. Easy drives to all the necessities, good pizza and gas stations. I enjoyed sitting on the screened in porch for breakfast and a late night beverage--we even saw a deer!"
Little House in the Woods by Evergreen Home

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate

The Race Mountain House

2.0 star property
The Race Mountain 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.
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Frequently asked questions

How many hotels that welcome pets are there in Sheffield?
Enjoy traveling with your furry pal at one of Expedia’s 5 Sheffield hotels that allow pets.
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 Magnolia Bluffs Casino and Housatonic River. While you’re there, make sure you don’t miss Three Mile Pond Wildlife Management Area and Mount Everett State Reservation.