Pet-friendly Hotels in Pittsfield

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Pet-friendly Hotels in Pittsfield

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Pittsfield on Hotels.com. These Pittsfield Pet-friendly Hotels consistently deliver on quality, location and traveler experience. Last updated on October 22, 2026.

A spacious room with large windows, a stone wall, and a wooden ceiling.

A cozy living room with a stone fireplace, leather sofa, and a patterned rug.

A spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.

A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.

1. The Mountain Top Inn & Resort

Chittenden

CNY1,969

CNY2,147 total

includes taxes & fees

Nov 1 - Nov 2

A sign for 'Apres Inn' in KILLINGTON, VT, with a modern building featuring large windows and a balcony.

A kitchen with a stove, oven, microwave, sink, and cabinets.

A room with a bed, a wooden wall-mounted bike rack, a microwave, a coffee maker, and a small refrigerator.

A sign for a hotel named 'Après Inn' in Killington, VT, indicating a vacancy.

2. Après Inn Killington

Killington

CNY921

CNY1,013 total

includes taxes & fees

Oct 25 - Oct 26

A building with a modern design, featuring large windows and a covered outdoor seating area.

A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.

A swimming pool surrounded by snow, with a building in the background.

A lobby with a stone wall, wooden staircase, and a reception desk.

3. The Mountain Inn at Killington

Killington

CNY895

CNY1,034 total

includes taxes & fees

Oct 25 - Oct 26

A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.

A modern hotel lobby with a dining area, stone wall, and a view of the outside.

A kitchen with wooden cabinets, a stainless steel refrigerator, a stove, and two bar stools.

A Best Western Inn & Suites with a well-maintained lawn, a parking area, and a building with a porch.

4. Best Western Inn & Suites Rutland-Killington

Rutland

CNY1,076

CNY1,183 total

includes taxes & fees

Nov 2 - Nov 3

A large, multi-story hotel with a prominent entrance and a staircase leading to the upper levels.

A stone fireplace with a modern seating area, including a sofa and chairs, a coffee table, and a decorative bowl.

A patio area with a fire pit, outdoor seating, and a swimming pool.

A hotel with a pool, multiple balconies, and a snow-covered ground.

5. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

CNY931

CNY1,024 total

includes taxes & fees

Nov 1 - Nov 2

A covered outdoor area with a wooden ceiling, potted plants, and a bench.

A conference room with tables, chairs, and a projector screen.

A gym with exercise equipment, a motivational wall, and a mirror.

A hotel room with a bed, bedside tables, a chair, and a patterned rug.

6. Hampton Inn Rutland

Rutland

CNY902

CNY992 total

includes taxes & fees

Nov 8 - Nov 9

A large, two-story house with a central courtyard, surrounded by a well-maintained lawn and trees.

A reception area with a decorative elephant sculpture, a framed picture, a clock, and a vase with flowers.

A large, two-story house with a well-maintained lawn and garden.

A large, two-story building with a courtyard featuring outdoor seating and a pathway.

7. The Lilac Inn

Brandon

CNY1,595

CNY1,755 total

includes taxes & fees

Oct 25 - Oct 26

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

A kitchen with white tiled backsplash, wooden crates, and hanging pendant lights.

A two-story house with a balcony, surrounded by lush greenery and a pond.

A two-story house with a snow-covered roof and a front porch.

8. On The River Inn

West Woodstock

CNY1,089

CNY1,332 total

includes taxes & fees

Nov 15 - Nov 16

A covered outdoor seating area with stone pillars and wooden beams, surrounded by a grassy lawn and trees.

A multi-story hotel with a parking lot, surrounded by autumn-colored trees and mountains in the background.

A modern restaurant with a bar area, seating arrangements, and a kitchen in the background.

Private kitchen

9. My Place Hotel-Randolph VT

Randolph Center

CNY616

CNY672 total

includes taxes & fees

Nov 22 - Nov 23

Front of property

A paved patio with outdoor furniture, a decorative garden bed, and a white fence.

A garden entrance with a white pergola covered in ivy, a sign indicating the pool is open, and outdoor seating with umbrellas.

A large house with a swimming pool, a fenced yard, and a well-lit entrance.

10. Brandon Inn

Brandon

CNY898

CNY988 total

includes taxes & fees

Nov 1 - Nov 2

A modern bedroom with a curved wall, a bed, a sofa, a small table with flowers, and a walk-in closet.

A swimming pool at dusk with surrounding lounge chairs and a covered area with lights.

A campground with several wooden cabins, a central fire pit area, and a well-maintained lawn.

A modern living room with a sofa, two round tables, a fireplace, and a television.

11. Emrose Luxury Cabins

Brandon

CNY1,202

CNY1,358 total

includes taxes & fees

Oct 26 - Oct 27

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

A modern kitchen with a wooden dining table, stainless steel appliances, and a view of the outdoors through the window.

A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.

A red car parked at a charging station in front of a building with a 'OPEN' sign.

12. Sleep Woodstock Motel

Woodstock

CNY517

CNY825 total

includes taxes & fees

Nov 19 - Nov 20

A room with a checkered floor, a bench, and a fireplace.

A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.

A spacious living room with a grand chandelier, large windows, and a comfortable seating area.

A spacious room with large windows, a fireplace, and comfortable seating areas.

13. Woodstock Inn & Resort

Woodstock

CNY2,463

CNY3,003 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living area with a fireplace, leather sofas, and a dining area with wooden furniture.

A spacious dining area with wooden tables and chairs, large windows offering a view of the outdoors, and a modern interior design with a wooden ceiling.

A reception desk with a wooden finish, a black textured wall, and a blue mat with 'Days Inn' text.

An indoor swimming pool with a high ceiling, multiple ceiling fans, and a seating area with chairs and tables.

14. Days Inn by Wyndham Rutland/Killington Area

Rutland

CNY789

CNY868 total

includes taxes & fees

Oct 25 - Oct 26

A modern fitness center with exercise equipment, mirrors, and a reception area.

A modern kitchen with white cabinets, a built-in oven, and a microwave.

A two-story building with a porch, a sign reading "STAY AT JIMMY'S", and a pathway leading to it.

A modern interior with a black wall-mounted sign reading "HANGOUT".

15. Stay At Jimmy's

Woodstock

CNY1,996

CNY2,196 total

includes taxes & fees

Oct 29 - Oct 30

A wooden cabin with a snow-covered roof, surrounded by trees and snow.

A wooden table with a bottle of wine, glasses, and grapes.

A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

A cozy cabin interior with a wooden dining table, chairs, a fireplace, a television mounted on the wall, and a large window with blinds.

16. Robert Frost Mountain Cabins

Ripton

CNY2,530

CNY2,758 total

includes taxes & fees

Oct 25 - Oct 26

An aerial view of a residential area with houses, a river, and surrounding hills.

A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

A two-story building with a central entrance, a small porch, and a driveway leading to a parking area.

An outdoor setting with a table and chairs, a small pond, and a wooden board game.

17. The Shire Woodstock

Woodstock

CNY814

CNY967 total

includes taxes & fees

Nov 22 - Nov 23

A two-story house with a front porch, a central entrance, and a garden with various plants and flowers.

A bar area with wooden bar stools, hanging light fixtures, and a bartender at the counter.

A hotel room with a large bed, bedside tables, a desk, and a chair.

A brick oven pizza station with a chef preparing dough.

18. Kedron Valley Inn

South Woodstock

CNY1,556

CNY1,712 total

includes taxes & fees

Nov 1 - Nov 2

A grocery store aisle with candy dispensers and bulk bins.

A hotel room with a TV on a desk, a chair, a lamp, and a bed with a red blanket.

A hotel room with two beds, a TV, and framed pictures on the wall.

A shower with a glass door, a toilet, and a sink with a granite countertop.

19. Middlebury Sweets Motel

Middlebury

CNY727

CNY800 total

includes taxes & fees

Oct 26 - Oct 27

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