Find Pet-friendly Hotels in Pittsfield, MA

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Top Pittsfield Pet-friendly Hotels

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (765)
"Quite and good location to around towns"
The price is SAR 597
SAR 666 total
includes taxes & fees
28 Sep - 29 Sep
Hotel On North

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (641)
"It’s a three star hotel charging 5 star prices. They should include free breakfast."
The price is SAR 596
SAR 666 total
includes taxes & fees
7 Sep - 8 Sep
Hilton Garden Inn Lenox Pittsfield

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

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

10.0 out of 10, Exceptional, (7)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Woodland 5-BR Retreat 5-Min to Jiminy Peak

10.0 out of 10, Exceptional, (9)
"We booked this house for a weekend getaway to visit friends that live close by. The house is amazing, great island in the kitchen which we would just hang out at. The front porch is great and the pool is 10/10. Bonus of having a solo stove fire pit as well. More than enough room for the 5 adults and 2 kids. Will definitely be booking again! "
Woodland 5-BR Retreat 5-Min to Jiminy Peak

Dancing Horse Lodge

9.4 out of 10, Exceptional, (45)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

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!"
The price is SAR 1,010
SAR 1,861 total
includes taxes & fees
11 Sep - 12 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Chic Pittsfield Home With A View!

8.2 out of 10, Very Good, (11)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & 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.

Top Pittsfield Hotel Reviews

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