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

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Check availability on Pittsfield Pet-Friendly Hotels

Our top choices for Pittsfield pet-friendly hotels

Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (592 reviews)
"Love that they catered to my dog. Will be back!"
United States
Mark
The price is Rp1.400.243
Rp1.540.268 total
includes taxes & fees
21 Jul - 22 Jul
Sleep Woodstock Motel
Elite Cabin, 1 King Bed, Sauna | Laptop workspace, blackout curtains, free WiFi, individually decorated

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (101 reviews)
"Very nice, clean place to stay in Brandon. Visited family over the years and this was by far the best stay...."
United States
Tim
The price is Rp2.930.742
Rp3.311.738 total
includes taxes & fees
27 Jul - 28 Jul
Emrose Luxury Cabins
Lobby

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (403 reviews)
"Clean room, friendly staff,helpful resources listed."
United States
Michael
The price is Rp2.589.587
Rp2.848.546 total
includes taxes & fees
17 Jul - 18 Jul
Middlebury Sweets Motel
Breakfast and dinner served

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,015 reviews)
"Great place to stay with the best staff!"
United States
Travis
The price is Rp2.426.003
Rp2.802.115 total
includes taxes & fees
20 Jul - 21 Jul
The Mountain Inn at Killington
BBQ/picnic Area

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (488 reviews)
"Have never stayed at a better kept facility"
United States
Karyssa
The price is Rp2.507.413
Rp2.733.007 total
includes taxes & fees
2 Aug - 3 Aug
My Place Hotel-Randolph VT
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

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Love that they catered to my dog. Will be back!"
Mark 2-night trip
Posted 15 hours 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.