Find Pet-friendly Hotels in Pittsfield, 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 Pittsfield Pet-friendly Hotels

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

Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (714)
"Exceptional hotel staff - friendly and accomodating from check-in to check-out. Room was clean and incredibly comfortable. Hotel was quiet and central to many locations we visited throughout our long weekend stay."
The price is SAR 413
SAR 461 total
includes taxes & fees
12 May - 13 May
Hotel On North
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (630)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is SAR 631
SAR 705 total
includes taxes & fees
29 May - 30 May
Hilton Garden Inn Lenox Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (141)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is SAR 1,121
SAR 1,952 total
includes taxes & fees
4 Jun - 5 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Chic Pittsfield Home With A View!
Property grounds

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
Woodland 5-BR Retreat 5-Min to Jiminy Peak
5 bedrooms, desk, iron/ironing board, WiFi

Woodland 5-BR Retreat 5-Min to Jiminy Peak

10.0 out of 10, Exceptional, (5)
"The house was beautiful, very clean and well kept."
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Interior

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Spacious Historic Home in the Berkshires!
TV, fireplace, books

Spacious Historic Home in the Berkshires!

9.8 out of 10, Exceptional, (10)
"Home was very well appointed! Beds comfy and very spacious rooms. We enjoyed both the front and back porches for our quiet gatherings. We were on the go most of the weekend, and this home was the perfect location for bopping around the Berkshires."
Spacious Historic Home in the Berkshires!
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!
Fridge, microwave, stovetop, dishwasher

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

9.6 out of 10, Exceptional, (5)
"We usually don’t book places that don’t have several reviews, but since we knew the area, we decided to “take a chance”. We are very glad we did! We stayed 5 nights and were very happy. The heat pumps were great since the temperature dipped below 0. The accommodations were very comfortable and we had everything we needed to make our stay enjoyable. "
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!
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.
Don't see what you're looking for?
See all available properties in Pittsfield

Frequently asked questions

What's the best pet-friendly accommodation in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top dog-friendly hotel, and offers a restaurant along with free WiFi for its human guests. Other good options for you and your pet’s trip include Best Western Plus Berkshire Hills Inn & Suites and Hotel On North.
How many hotels that welcome pets will I be able to find in Pittsfield?
Frolic with your furry friend at one of Expedia’s 5 Pittsfield hotels that allow pets.
What's the best time of year to travel to Pittsfield with my pet?
When you travel with your pet, keeping track of the weather can make the trip 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 27°F. The snowiest months in Pittsfield 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 Pittsfield?
Known for its baseball and entertainment, Pittsfield has lots to offer visitors including its theaters, opera, and museums. See the local sights and visit Berkshire Museum and Colonial Theater. While you’re there, make sure you don’t miss Barrington Stage Company and Bousquet Ski Area.