Search Pet-Friendly Hotels in Pittsfield

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Our top choices for Pittsfield pet-friendly hotels

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is ฿2,601
฿4,824 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (346)
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is ฿3,173
฿3,458 total
includes taxes & fees
4 Jan - 5 Jan 2026
My Place Hotel-Randolph VT

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (656)
"Very quiet and comfortable stay."
United States
James
The price is ฿3,738
฿4,111 total
includes taxes & fees
23 Dec - 24 Dec
Cortina Inn

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (893)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (566)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is ฿3,756
฿4,132 total
includes taxes & fees
23 Dec - 24 Dec
Brandon Inn

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (972)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is ฿5,209
฿5,730 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Rutland

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (388)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is ฿3,075
฿3,382 total
includes taxes & fees
30 Dec - 31 Dec
Middlebury Sweets Motel

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is ฿7,821
฿8,603 total
includes taxes & fees
23 Dec - 24 Dec
Stay At Jimmy's

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (164)
"Wonderful location, beautiful renovations, friendly staff "
United States
Robyn
The price is ฿6,068
฿6,675 total
includes taxes & fees
13 Jan - 14 Jan 2026
Après Inn Killington
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

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.