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

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Check availability on Pittsfield Pet-friendly Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Pittsfield pet-friendly hotels

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

1. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Winter Wonderland

2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A spacious room with large windows, a stone wall, and a wooden ceiling.

3. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.2 out of 10, Wonderful, (131 reviews)
"Oh wow!! I would stay here again tomorrow! Beautiful property, restaurant has amazing food and convenient location. We stayed in the Long View Barn, the 60 mile view was even more spectacular than we imagined!"
United States
Allison
The price is AED 943
AED 1,208 total
includes taxes & fees
9 Nov - 10 Nov
The Mountain Top Inn & Resort
A spacious living room with a fireplace, a television, and a large window.

4. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
4BR Killington Home Perfect for Families, Pet-Friendly
A wooden shed with a cross-braced door in a garden with a house in the background.

5. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
North Sherburne
8.0 out of 10, Very good, (16 reviews)
"We had a great time!"
United States
Matthew R.
The price is AED 483
AED 1,575 total
includes taxes & fees
15 Nov - 16 Nov
Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
A building with a modern design, featuring large windows and a covered outdoor seating area.

6. The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,033 reviews)
"Great hotel!"
United States
Petra
The price is AED 493
AED 569 total
includes taxes & fees
1 Nov - 2 Nov
The Mountain Inn at Killington
A sign for 'Apres Inn' in KILLINGTON, VT, with a modern building featuring large windows and a balcony.

7. Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (206 reviews)
"modern and clean, wifi worked great"
United States
Kylie
The price is AED 507
AED 558 total
includes taxes & fees
31 Oct - 1 Nov
Après Inn Killington
A modern house with a stone facade, a large deck, and outdoor seating.

8. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Killington
9.0 out of 10, Wonderful, (6 reviews)
"The accommodations exceeded the expectations in all ways.The booking, check in and communication with the hosts we're problem free and I would highly recommend this property and host to everyone seeking a beautiful and stress free get away."
United States
SHEEPDOG 1.
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

9. The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AED 984
AED 3,178 total
includes taxes & fees
11 Nov - 12 Nov
The Tower House | Hot Tub | Firepit | Dog-Friendly
A stone fireplace with a black mantel, framed picture, and decorative items.

10. SnowArts, Wood Burning fireplace, Close to slopes

SnowArts, Wood Burning fireplace, Close to slopes
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place for a large group. It was pet friendly and that is a plus for us. Very clean and reasonably priced."
United States
Tammy W.
The price is AED 1,625
AED 3,245 total
includes taxes & fees
31 Oct - 1 Nov
SnowArts, Wood Burning fireplace, Close to slopes
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
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."
Darrah 1-night trip
Posted 2 days ago
Woodstock Inn & Resort

Frequently asked questions

What's the best pet-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 traveling with pets, keeping track of the weather can make the trip safe and fun for everyone. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches 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 Pittsfield Town Hall. While you're there, make sure you don't miss Roger Clark Memorial Central Library.

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