Photo by William Keller

Find Pet-friendly Hotels in Stockbridge, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Pet-friendly Hotels

Our top choices for Stockbridge pet-friendly hotels

Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1004)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NT$4,724
NT$6,684 total
includes taxes & fees
Jan 14 - 2026/1/15
The Red Lion Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is NT$3,464
NT$3,801 total
includes taxes & fees
Dec 18 - Dec 19
Shaker Mill Inn
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
The price is NT$4,109
NT$4,590 total
includes taxes & fees
Dec 23 - Dec 24
Element Lenox Berkshires
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is NT$2,405
NT$2,687 total
includes taxes & fees
Jan 4 - 2026/1/5
Best Western Plus Berkshire Hills Inn & Suites
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is NT$3,146
NT$3,514 total
includes taxes & fees
Jan 15 - 2026/1/16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is NT$7,904
NT$9,880 total
includes taxes & fees
Dec 21 - Dec 22
Prospect Berkshires
Courtyard
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (88)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is NT$3,685
NT$4,043 total
includes taxes & fees
Dec 18 - Dec 19
The Springs Motel
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (989)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
The price is NT$2,948
NT$3,293 total
includes taxes & fees
Dec 19 - Dec 20
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is NT$3,450
NT$3,854 total
includes taxes & fees
Jan 1 - 2026/1/2
The Little Lion
Balcony
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NT$2,801
NT$3,129 total
includes taxes & fees
Dec 25 - Dec 26
The Central Downtown Inn & Suites
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.
View all properties

Top Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"A magical, magical New England weekend at The Red Lion Inn. The room was so warm, the bed and pillows were so comfortable and just the right firmness. The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night. Check in was a breeze, staff were warm and welcoming. Highly recommend making reservations at their Tavern or Dining Area. Several small cafes and charming local shops close by for Christmas shopping"
Judith Pauline 1-night trip
Posted 1 day ago
The Red Lion Inn

Explore a world of travel with Expedia

Frequently asked questions

What's the best pet-friendly place to stay in Stockbridge?
The Red Lion Inn is a top hotel for people traveling with their pets, and offers 3 restaurants and an outdoor pool for its human guests.
What's the best time of year to travel to Stockbridge with my pet?
When you're traveling with pets, keeping track of the weather can help you make the trip more 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 Stockbridge 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 Stockbridge?
Known for its gardens and museums, Stockbridge has lots to offer visitors including its hiking trails, architecture, and monuments. See the local sights and visit Naumkeag Museum and National Shrine of the Divine Mercy. While you're there, make sure you don't miss Norman Rockwell Museum and Berkshire Botanical Garden.