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, (697)
"Staff was very helpful and kind"
The price is AED 444
AED 496 total
includes taxes & fees
6 Apr - 7 Apr
Hotel On North

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (629)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is AED 514
AED 575 total
includes taxes & fees
4 May - 5 May
Hilton Garden Inn Lenox Pittsfield

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

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Dancing Horse Lodge

9.4 out of 10, Exceptional, (40)
"Cozy home with a cabin like feel. Plenty of room and warmth. The 3 bedrooms accommodated our group perfectly! Easy check in instructions"
Dancing Horse Lodge

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

Spacious Historic Home in the Berkshires!

9.8 out of 10, Exceptional, (10)
"This property was charming. It's a very old house, BUT, a lot of it was updated with modern fixtures and touches. Really cool and artistic artwork around the home. We were 2 families with 4 kids. There was enough space for all. The host was super friendly and very responsive, as was the owner. We had a bit of an issue with the thermostat as it wasn't working too well when we were there, but the owner quickly responded and helped to fix. We were there for our 2nd annual family ski trip to...
Spacious Historic Home in the Berkshires!

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

10.0 out of 10, Exceptional, (4)
"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Chic Pittsfield Home With A View!

8.2 out of 10, Very Good, (11)
"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 AED 1,098
AED 1,953 total
includes taxes & fees
5 Apr - 6 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Renovated Pittsfield Colonial by Evergreen Home

10.0 out of 10, Exceptional, (34)
"What a stay! We enjoyed this house and all of the amenities. The booking process was seamless and came with additional services like photographer, masseuse, and personal chef. The communication was absolutely superb, the house was very accommodating, spacious, and super comfortable! We made family memories that will last a lifetime! Thank you to the team and this beautiful home ! "
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 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 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 Barrington Stage Company and Bousquet Ski Area.