Find Pet-friendly Hotels in Pittsfield, MA

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Check availability on Pittsfield Pet-friendly Hotels

Top Pittsfield Pet-friendly Hotels

Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (736)
"Best hotel in the Berkshire! "
The price is SARĀ 567
SARĀ 633 total
includes taxes & fees
30 Jun - 1 Jul
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, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is SARĀ 737
SARĀ 824 total
includes taxes & fees
23 Jun - 24 Jun
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, (144)
"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
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, (7)
"The house was beautiful, very clean and well kept."
Woodland 5-BR Retreat 5-Min to Jiminy Peak
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!"
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!

8.2 out of 10, Very Good, (11)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
Elegant Pittsfield Home Near Downtown & Skiing!
House (5 Bedrooms) | Interior

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
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

10.0 out of 10, Exceptional, (1)
"We were staying for an event in Adams and didn't need much... Stepping inside the cottage was a delight!! A great deal of thought and design has gone into making this little old lake cottage, into a lovely, friendly and comfortable place to stay. I hope we will have cause to return. "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Hidden Oasis in the Mountains by Evergreen Home
Property grounds

Hidden Oasis in the Mountains by Evergreen Home

10.0 out of 10, Exceptional, (8)
"Our family enjoyed our week long stay in this beautiful home. Morning coffee on the screened porch watching the leaves change color each day was just so relaxing. This home has all of the amenities a family needs and we would love to stay here again. The property manager was extremely helpful and timely in communicating with us."
Hidden Oasis in the Mountains by Evergreen Home
Spacious Historic Home in the Berkshires!
TV, fireplace, books

Spacious Historic Home in the Berkshires!

10.0 out of 10, Exceptional, (11)
"We had a great long weekend at this house and skiing at Jiminy Peak. The house was spacious and well equipped for us to cook and enjoy family dinners and family time. We brought our dogs and they loved it too! "
Spacious Historic Home in the Berkshires!
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

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 66Ā°F, while the coldest months are January and February with an average of 27Ā°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.