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Top Pittsfield Pet-Friendly Hotels

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (745)
"Original design and funky atmosphere. Friendly and
pet friendly
. Will come back. "
Benjamin Antonio
The price is £157
includes taxes & fees
27 Jul - 28 Jul
Hotel On North

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Our room was very comfortable and quiet so that was good. It is not in a very scenic location, but that seems to be typical in this area. It is on the highway overlooking some other businesses but there is a very popular food market there close by which is nice."
Jan
The price is £163
includes taxes & fees
27 Jul - 28 Jul
Hilton Garden Inn Lenox Pittsfield

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

9.8 out of 10, Exceptional, (146)
"House is just gorgeous. Very large and comfortable for a larger group. I could not believe how stocked it was. Crock pots, blenders, etc. About a 5 minute ride to a lovely park with swimming lake and facilities. You could walk in about 20 minutes. Neighbors were friendly and quiet area. Hit up Jiminy peak if you have kids! Lenox is also a nice town to walk around and hit some cute shops. First time staying in the Berkshires, but won’t be the last. It was a heat wave week so house did get a bit...
STEPHANIE M.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
The price is £459
includes taxes & fees
4 Aug - 5 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Dancing Horse Lodge

9.4 out of 10, Exceptional, (44)
"We traveled to the Berkshires to visit with friends who recently moved there. This was a great spot to stay and it is
pet friendly
. Very convenient to lots of wonderful little towns,
parks
and awesome trails. 😊"
Heidi W.
Dancing Horse Lodge

Woodland 5-BR Retreat 5-Min to Jiminy Peak

10.0 out of 10, Exceptional, (8)
"We stayed here for a Basketball tournament and it was GORGEOUS! Although we did not spend much time in the home it was so comfortable and spacious for our Teammates that did stay with us. I recommended 100% staying here!"
Amy S.
Woodland 5-BR Retreat 5-Min to Jiminy Peak

Chic Pittsfield Home With A View!

8.2 out of 10, Very good, (11)
"Apart from the smell of an old house, the stay was okay overall. One will require extra laundry and cleaning for their clothing if they use CPAP. The surrounding is wooded, but we still think better curtains would be nice. Fencing was excellent around the house and helped keep our pet inside. The exterior view is not what it seems like in the advertisement photographs, which are most likely from when it was renovated."
Ansuman P.
Chic Pittsfield Home With A View!

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (4)
"A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! "
Nicholas S.
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!

Spacious Historic Home in the Berkshires!

3.0 star property
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.

Top Pittsfield Hotel Reviews

Frequently asked questions

What's the best dog-friendly accommodation option in Pittsfield?
Best Western Plus Berkshire Hills Inn & Suites is a top dog-friendly hotel, and offers a fitness centre along with free WiFi for its human guests. Two other good options for you and your pet's trip include Holiday Inn & Suites Pittsfield-Berkshires by IHG and Hilton Garden Inn Lenox Pittsfield.
How many hotels that welcome pets are there in Pittsfield?
Frolic with your furry friend at one of Expedia's 5 Pittsfield accommodation options that accept 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 theatres, 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 Herman Melville's Arrowhead.