Find Pet-friendly Hotels in Pittsfield, MA

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Pet-friendly Hotels

Tonight
Sep 4 - Sep 5
Tomorrow
Sep 5 - Sep 6
This weekend
Sep 5 - Sep 7
Next weekend
Sep 12 - Sep 14

Top Pittsfield Pet-friendly Hotels

Our top choices for Pittsfield pet-friendly hotels

Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (768)
"Quite and good location to around towns"
The price is ￥23,605
￥26,366 total
includes taxes & fees
Sep 28 - Sep 29
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, (641)
"We always stay at the Garden Inn when visiting the Berkshires."
The price is ￥23,519
￥26,271 total
includes taxes & fees
Sep 14 - Sep 15
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
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, (7)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
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, (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
Fridge, microwave, oven, stovetop

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!
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 ￥39,840
￥72,285 total
includes taxes & fees
Sep 11 - Sep 12
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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!
Renovated Pittsfield Colonial by Evergreen Home
Interior

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
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!
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

Explore a world of travel with Expedia

Explore a world of travel with Expedia