Find Pet-friendly Hotels in Sheffield, MA

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Check availability on Sheffield Pet-friendly Hotels

Tonight
26 Apr - 27 Apr
Tomorrow
27 Apr - 28 Apr
Next weekend
2 May - 4 May
In two weeks
9 May - 11 May

Compare Sheffield Pet-friendly Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AED 1,855
AED 3,188 total
includes taxes & fees
28 Apr - 29 Apr
Guesthouse Cabin vacation rentals in Berkshire County
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (86)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AED 687
AED 1,621 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
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
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
Fridge, oven, stovetop, dishwasher

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

9.8 out of 10, Exceptional, (6)
"We had everything we needed for a short stay in the Berkshires. It was a perfect location for us and we would happily stay again!"
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
River Orchard Meadow
Fridge, microwave, oven, stovetop

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.
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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 Housatonic River and Magnolia Bluffs Casino. While you’re there, make sure you don’t miss Ashley House and Mount Everett State Reservation.