TOP Pet Friendly Hotels in Pittsfield for 2025 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels

Check availability on Pittsfield Pet friendly Hotels

Tonight

Tomorrow

This weekend

Next weekend

Top Pet friendly Hotels in Pittsfield

"Staff was very professional and friendly! River the Inn was beautiful! "

Find out more about Pittsfield

Pittsfield Pet friendly Hotels information

Pet friendly Hotels in Pittsfield	14
Highest price
Cheapest price
Number of guest reviews	85
Total number of hotels in Pittsfield	1,669

Recent Reviews in Pittsfield

5/5 Excellent

Perfect Spot

"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "

A verified traveller stayed at Woodstock Inn & Resort

Posted 5 days ago

5/5 Excellent

"Sleep Woodstock is a great economic option to stay when visiting the Killington Ski Mountain. It’s only 15 minutes away and convenient to get to. Sleep Woodstock is also very close to Woodstock with its great option for dinning no shopping. The room was also clean and new. The Sleep Woodstock team also kept the parking area plowed and easy to access even during a huge snow storm. Kudos to everyone."

A verified traveller stayed at Sleep Woodstock Motel

Posted 7 days ago

Explore a world of travel with Expedia

Explore a world of travel with Expedia

More Accommodation Types in Pittsfield

Hotels near other Attractions

Explore more hotels

See a list of all hotels in Pittsfield

More ways to book

Book Pet friendly Hotels in Pittsfield on Expedia.com

Frequently asked questions

What's the best dog-friendly place to stay in Pittsfield?

Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests.

How many hotels that accept pets will I be able to find in Pittsfield?

Enjoy travelling with your furry pal at one of Expedia’s 7 Pittsfield accommodation options that accept pets.

What's the best time of year to travel to Pittsfield with my pet?

When you’re travelling with pets, keeping tabs on the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -5°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.

What is there to see and do with your pet in Pittsfield?

See the local sights and visit Green Mountain National Forest. When you’re in the area, make time for a stop at Killington Resort.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Find Cat & Dog Friendly Hotels in Pittsfield

Plan, book, stay with confidence

Check availability on Pittsfield Pet friendly Hotels

Top Pet friendly Hotels in Pittsfield

Clear River Inn

Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 Min To Killington 3 Bedroom Home by RedAwning

Sweet Life - GetAway

Silver Spring Chalet - GetAway