A lake surrounded by autumn-colored trees and a rocky shoreline.

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Check availability on Pittsfield Pet-Friendly Hotels

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Pittsfield pet-friendly hotels

Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is ₹24,045
₹26,450 total
includes taxes & fees
2 Aug - 3 Aug
Stay At Jimmy's
Property grounds

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (968 reviews)
"Absolutely beautiful setting! The room was better than expected-- spacious, clean and gorgeously decorated. The location was also great-- everything was walkable. Highly recommend."
United States
Frances
The price is ₹23,963
₹28,468 total
includes taxes & fees
18 Aug - 19 Aug
The Shire Woodstock
Exterior

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (338 reviews)
"I love staying at the Inn when I come to Vermont to see my friends compete at Green Mountain Horse Association. Cozy place."
United States
Marylynn
The price is ₹27,725
₹30,497 total
includes taxes & fees
29 Jul - 30 Jul
Kedron Valley Inn
Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (595 reviews)
"As always - best hotel in Vermont."
United States
ben
The price is ₹52,644
₹62,127 total
includes taxes & fees
5 Aug - 6 Aug
Woodstock Inn & Resort
Deluxe Suite | Private kitchen | Coffee/tea maker, mini-fridge, microwave, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (595 reviews)
"This place was the BEST find!!! It was sparkling clean, everything new, everything you could possibly need. Keyless Entry works very well. Very dog friendly including dog bones, bowls, towel etc. The town of Woodstock is adorable so I will be back so I can explore more!!!!"
United States
Robin
The price is ₹7,474
₹8,222 total
includes taxes & fees
10 Aug - 11 Aug
Sleep Woodstock Motel
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.
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Top Pittsfield Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Quaint New England charm with beautifully maintained grounds. We enjoyed both the spa and the Red Rooster restaurant which were both wonderful. There was a wedding onsite one night while we were there and while beautiful, made it difficult to enjoy the outside fire and smores that evening as it was very loud. It was remarkable that you could not however hear the noise from inside the Inn. Overall I would highly recommend the Woodstock Inn resort & spa to couples, families and friend trips."
Julie 2-night trip
Posted 7 hours ago
Woodstock Inn & Resort
Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"This place was the BEST find!!! It was sparkling clean, everything new, everything you could possibly need. Keyless Entry works very well. Very dog friendly including dog bones, bowls, towel etc. The town of Woodstock is adorable so I will be back so I can explore more!!!!"
Robin 1-night trip
Posted 2 days ago
Sleep Woodstock Motel

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.
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 and Roger Clark Memorial Central Library. While you're there, make sure you don't miss Pittsfield Town Hall.