Find Pet-friendly Hotels in Pittsfield, MA

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Check availability on Pittsfield Pet-friendly Hotels

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

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (680)
"Had a great stay - such a gem of a hotel. "
The price is ¥17,263
¥19,282 total
includes taxes & fees
Feb 9 - Feb 10
Hotel On North

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (626)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is ¥20,139
¥22,495 total
includes taxes & fees
Feb 3 - Feb 4
Hilton Garden Inn Lenox Pittsfield

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!

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 ¥46,085
¥81,950 total
includes taxes & fees
Feb 16 - Feb 17
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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

10.0 out of 10, Exceptional, (2)
"The house was fantastic. It had more rooms than we needed, everything was clean, the dining/living area had a lot of lighting, and there was a large fenced in backyard which our dogs loved running around in. It was a great getaway for us as we were coming from Brooklyn. Grocery stores were only 15 min away. Would highly recommend booking! When there was a minor issue, our host Lindsey was very communicative and had it solved right away!"
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

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

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Spacious Historic Home in the Berkshires!

9.8 out of 10, Exceptional, (7)
"Very nice. Old house but expected where we were staying. Beautiful town and within walking distance to restaurants and shopping. Mattress were on the hard side if you like that. We like that so it was good. "
Spacious Historic Home in the Berkshires!

Elegant Pittsfield Home Near Downtown & Skiing!

10.0 out of 10, Exceptional, (16)
"We truly enjoyed our week in Pittsfield and the Berkshires. The kitchen was extremely well-stocked with every appliance imaginable and access to a full pantry. Loved the location. Gas fireplace was an added benefit. Rooms, bathrooms and closet space were perfect. Definitely recommend! "
Elegant Pittsfield Home Near Downtown & Skiing!

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
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 Hotel On North and Best Western Plus Berkshire Hills Inn & Suites.
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.