Find Pet-friendly Hotels in Pittsfield, MA

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Check availability on Pittsfield Pet-friendly Hotels

Our top choices for Pittsfield pet-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AED 346
AED 387 total
includes taxes & fees
5 Jan - 6 January 2026
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 340
AED 380 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Balcony
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AED 328
AED 366 total
includes taxes & fees
15 Dec - 16 Dec
The Central Downtown Inn & Suites
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is AED 379
AED 423 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield
Property entrance
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Clean room and staff was super friendly"
United States
Yuen
The price is AED 547
AED 611 total
includes taxes & fees
14 Dec - 15 Dec
Hotel On North
Outdoor dining
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AED 988
AED 1,797 total
includes taxes & fees
13 Dec - 14 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is AED 481
AED 537 total
includes taxes & fees
17 Dec - 18 Dec
Element Lenox Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is AED 396
AED 435 total
includes taxes & fees
14 Dec - 15 Dec
Shaker Mill Inn
Courtyard
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is AED 399
AED 438 total
includes taxes & fees
12 Dec - 13 Dec
The Springs Motel
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is AED 372
AED 415 total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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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Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The best of the best A definite destination and accommodations"
Seth 1-night trip
Posted 3 days ago
The Red Lion Inn

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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 Bousquet Ski Area and Hancock Shaker Village.