Find Pet-friendly Hotels in Sheffield, MA

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Pick from 13 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, (29)
"Sabrina saw to everything. The house even came equipped with a spice drawer, games like badminton equipment, a kid’s bedroom with games and books, and nice touches like vases of flowers. Our family was amazed and impressed. The outdoor area in the front (and back) was big enough for our grandchildren to play badminton. We very highly recommend this place!"
The price is SAR 815
SAR 1,800 total
includes taxes & fees
18 Nov - 19 Nov
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 3,357 total
includes taxes & fees
17 Nov - 18 Nov
Guesthouse Cabin vacation rentals in Berkshire County
Whitney by AvantStay | Private Berkshires Estate
8.4 out of 10, Very Good, (9)
"This is a lovely older home with lots of character, warm and inviting. Beautiful property and great views. We spent a fabulous weekend enjoying the fall beauty of the Berkshires."
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 Ashley House. While you’re there, make sure you don’t miss Mount Everett State Reservation and Housatonic River.