Find Pet-friendly Hotels in Pittsfield, MA

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Pick from 24 Pittsfield Pet-friendly Hotels and compare 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, (650)
"Very nice!"
The price is AED 533
AED 595 total
includes taxes & fees
25 Nov - 26 Nov
Hotel On North
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (618)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions. "
The price is AED 501
AED 559 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Lenox Pittsfield
Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

8.8 out of 10, Excellent, (8)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
Dancing Horse Lodge
Dancing Horse Lodge - Entrance View

Dancing Horse Lodge

9.6 out of 10, Exceptional, (36)
"nice"
Dancing Horse Lodge
Spacious Historic Home in the Berkshires!
Pittsfield Vacation Rental | 5BR | 2BA | Stairs Required | 3,300 Sq Ft

Spacious Historic Home in the Berkshires!

9.6 out of 10, Exceptional, (5)
"This lovely home was ideal for my family of 8: my children and their spouses, two grandchildren, myself and two pups. The beds were plentiful and comfortable. The house, while old, was newly remodeled, adding modern appliances to the charm of the original building. Very bright and spacious in a quiet neighborhood, convenient to Lenox, Tanglewood, and other special towns. I highly recommend this home to anyone looking for a pleasant retreat. We loved every minute!"
Spacious Historic Home in the Berkshires!
Woodland 5-BR Retreat 5-Min to Jiminy Peak

Woodland 5-BR Retreat 5-Min to Jiminy Peak

10.0 out of 10, Exceptional, (5)
"This was a great house for six adults to spend most of a week at. It was certainly the cleanest VRBO I've ever rented -- the dishes, silverware and everything in the kitchen was ready to go at check in. Bathrooms and bedrooms were also ultra clean. Kitchen was well stocked with utensils, plates and pots/pans. The rooms were bright both day and night. The large island kitchen was ideal for hanging out at and chatting with friends and family. There is a large yard off to the side of the...
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Renovated Pittsfield Colonial by Evergreen Home
Welcome!!

Renovated Pittsfield Colonial by Evergreen Home

10.0 out of 10, Exceptional, (33)
"This spacious home perfectly accommodated our group. Awesome common area and kitchen. Extremely clean on arrival. We have stayed here twice now!"
Renovated Pittsfield Colonial by Evergreen Home
Spacious Historic Home in the Berkshires!
Property grounds

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
51 Seymour St
Living area

51 Seymour St

3.5 star property
51 Seymour St
Perfect for Winter Skiing!!
Exterior

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
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

What's the best pet-friendly accommodation in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel 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 Hilton Garden Inn Lenox Pittsfield.
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 Pittsfield State Forest.