Find Pet-friendly Hotels in Pittsfield, MA from CA $258

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Check availability on Pittsfield Pet-friendly Hotels

Tonight
Jul 25 - Jul 26
Tomorrow
Jul 26 - Jul 27
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Top Pittsfield Pet-friendly Hotels

Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (745)
"Staff were excellent and welcoming."
The price is CA $258
CA $288 total
includes taxes & fees
Aug 3 - Aug 4
Hotel On North
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is CA $281
CA $314 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Lenox Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

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
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Exterior

Woodland 5-BR Retreat 5-Min to Jiminy Peak

10.0 out of 10, Exceptional, (8)
"The house was beautiful, very clean and well kept."
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.4 out of 10, Exceptional, (44)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
Chic Pittsfield Home With A View!
Property grounds

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

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! "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

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 CA $490
CA $828 total
includes taxes & fees
Aug 4 - Aug 5
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Elegant Pittsfield Home Near Downtown & Skiing!
House (5 Bedrooms) | Front of property

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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
Edward 2-night trip
Posted 4 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What's the best pet-friendly accommodation in Pittsfield?
Best Western Plus Berkshire Hills Inn & Suites is a top dog-friendly hotel, and offers a fitness center along with free WiFi for its human guests. 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 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 Herman Melville's Arrowhead.