Find Pet-friendly Hotels in Sheffield, MA

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Sheffield Pet-friendly Hotels

Tonight
30 May - 31 May
Tomorrow
31 May - 1 Jun
This weekend
30 May - 1 Jun
Next weekend
6 Jun - 8 Jun

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, (6)
"Really enjoyed the cabin. The pictures donā€™t do the view justice as itā€™s an amazing vista overlooking the Berkshires. "
The price is AEDĀ 1,855
AEDĀ 3,188 total
includes taxes & fees
2 Jun - 3 Jun
Guesthouse Cabin vacation rentals in Berkshire County
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (87)
"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, (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
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (37)
"The property was centrally located for skiing, and was a comfortable stay."
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
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!
Whitney by Avantstay Private Berkshires Estate
Interior

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
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
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
Modern Dairy Barn with Ample Natural Light and 2 Living Rooms!
Smart TV, fireplace, video games

Modern Dairy Barn with Ample Natural Light and 2 Living Rooms!

Modern Dairy Barn with Ample Natural Light and 2 Living Rooms!
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 Expediaā€™s 5 Sheffield hotels that allow pets.
What's the best time of year to travel to Sheffield with my pet?
When youā€™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 66Ā°F, while the coldest months are January and February with an average of 28Ā°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 youā€™re there, make sure you donā€™t miss Ashley House and Mount Everett State Reservation.