Find Pet-friendly Hotels in Sheffield, MA

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Check availability on Sheffield Pet-friendly Hotels

Top Sheffield Pet-friendly Hotels

Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (7)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is SAR 1,894
SAR 3,255 total
includes taxes & fees
5 Aug - 6 Aug
Guesthouse Cabin vacation rentals in Berkshire County
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (89)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (2)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is SAR 1,001
SAR 2,015 total
includes taxes & fees
31 Jul - 1 Aug
Cheerful 3-bedroom cottage with woodstove
Whitney by AvantStay | Private Berkshires Estate
Exterior

Whitney by AvantStay | Private Berkshires Estate

8.2 out of 10, Very Good, (11)
"Great old house with charming details and well equipped with modern conveniences. The views outside of the mountains and meadow next door were a nice bonus. Communication and attentiveness to any questions or issues were quickly taken care of. Overall a great trip!"
Whitney by AvantStay | Private Berkshires Estate
Whitney by Avantstay Private Berkshires Estate
Interior

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Little House in the Woods by Evergreen Home
Fridge, microwave, oven, stovetop

Little House in the Woods by Evergreen Home

10.0 out of 10, Exceptional, (33)
"This was a perfect quiet serene location on a beautiful property. Would love to visit again"
Little House in the Woods by Evergreen Home
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
Property grounds

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

9.8 out of 10, Exceptional, (36)
"We really enjoyed our stay here - location was great and being surrounded by the lake was amazing. The owner was super responsive and helped us out with a minor issue right away. Highly recommend!"
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
River Orchard Meadow
Property grounds

River Orchard Meadow

8.0 out of 10, Very Good, (1)
"Comfortable and centrally located to beautiful surroundings and towns."
River Orchard Meadow
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.

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 Housatonic River and Magnolia Bluffs Casino. While you're there, make sure you don't miss Mount Everett State Reservation and Thom Reed UFO Monument Park.