𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Pittsfield (2026)

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

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Go beyond your typical stay in Pittsfield

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Our top choices for Pittsfield hotels

Hotel

Breakfast included

Reserve now, pay later

Motel

Pet friendly

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

A large building with a covered entrance and multiple windows, surrounded by a grassy area and trees with autumn foliage.

A cozy living room with wooden furniture, a fireplace, and a television.

A cozy living room with a fireplace, a white sofa, a coffee table with candles, and a bag with the text "Love is All Around".

1. The Trailside Inn

North Sherburne

Niall

S$222

includes taxes & fees

31 Aug - 1 Sept

A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.

A spacious living room with a wooden dining table, a sofa, and a coffee table. There is a large rug on the floor and a fireplace in the background.

A kitchen with wooden cabinets, a refrigerator, a stove, a microwave, and a sink.

A wooden cabin with a white door labeled "Outer Limits," a covered porch, and a snow-covered deck.

2. Mountain Sports Inn

Killington

Davis

S$152

includes taxes & fees

27 Aug - 28 Aug

A calm lake surrounded by autumn-colored trees and a clear blue sky.

A cozy living room with a stone fireplace, leather sofas, a round coffee table, and a large window offering a view of the outdoors.

A room with wooden cabinets, potted plants, and hanging light fixtures.

A bar area with wooden stools, pendant lighting, and a rustic ceiling.

3. Mountain Meadows Lodge

Killington

Barry

S$217

includes taxes & fees

27 Aug - 28 Aug

A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

A multi-story building with a pool and a covered patio area.

A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.

4. North Star Lodge and Resort

Killington

Corey

S$166

includes taxes & fees

8 Sept - 9 Sept

A table with a checkered placemat, a red vase with greenery and berries, and a clear plastic bag with items.

A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

A sign for Greenbrier Inn and a gift shop, with a snow-covered ground.

A spacious loft-style living area with a high ceiling, wooden beams, and a cozy fireplace. A staircase with a wooden railing leads to an upper level.

5. Greenbrier Inn

Killington

David

S$247

includes taxes & fees

27 Aug - 28 Aug

A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

A wooden interior with a dining area featuring a round table and benches, large windows with a view of greenery, and a sign that reads "Grateful."

A cozy cabin interior with a stone fireplace, wooden furniture, and a stone wall.

A golf course with a winding road, surrounded by trees and mountains.

6. Snowed Inn

Killington

James

S$195

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

7. The Mountain Inn at Killington

Killington

Allison

S$183

includes taxes & fees

2 Sept - 3 Sept

A hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.

A hotel room with two beds, a desk, a chair, a lamp, and a trash can.

A brick building with a sign reading 'Southside Steakhouse' and the number '170' above the entrance.

A modern hotel lobby with a blue sofa, a round coffee table, and abstract art on the walls.

8. Comfort Inn Rutland - Killington

Rutland

Tracy

S$186

includes taxes & fees

30 Aug - 31 Aug

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

A modern kitchen with white cabinets, a stainless steel dishwasher, and a microwave.

9. Best Western Inn & Suites Rutland-Killington

Rutland

Alex

S$250

includes taxes & fees

30 Aug - 31 Aug

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

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

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

10. Après Inn Killington

Killington

Margaret

S$193

includes taxes & fees

31 Aug - 1 Sept

A modern interior with a wooden counter, seating area, and large windows.

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

A modern lounge area with orange upholstered chairs, a fireplace, and large windows offering a view of autumn trees.

A hotel entrance with a covered walkway, stone pillars, and a sign reading "Haywood Inn."

11. Hampton Inn Rutland

Rutland

Brent

S$199

includes taxes & fees

6 Sept - 7 Sept

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.

12. The Mountain Top Inn & Resort

Chittenden

Kristen

S$450

includes taxes & fees

1 Sept - 2 Sept

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

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

A hotel room with two beds, a desk, and a chair. The room has a wooden floor and red walls with framed pictures.

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

13. Sleep Woodstock Motel

Woodstock

Sean

S$119

includes taxes & fees

31 Aug - 1 Sept

A wooden structure with a black door labeled "KILLINGTON HAUS GUEST ENTRANCE" and a sign saying "WELCOME GUESTS!".

A modern interior with a kitchen area, seating, and a fireplace.

A bedroom with a red bed, white bedding, a window with blinds, a desk with a chair, and a wall-mounted lamp.

A wall with a colorful mural featuring the text "Greetings from KELINGTON, VERMONT."

14. Killington Haus

Killington

Samir

S$151

includes taxes & fees

2 Sept - 3 Sept

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

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

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

15. My Place Hotel-Randolph VT

Randolph Center

Joey

S$222

includes taxes & fees

23 Sept - 24 Sept

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

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

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

A spacious loft-style living area with high ceilings, exposed wooden beams, and a mezzanine level.

16. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

Joseph

S$217

includes taxes & fees

30 Aug - 31 Aug

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

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

A long corridor with tables and chairs, large windows, and a ceiling fan.

17. Brandon Inn

Brandon

Michael

S$201

includes taxes & fees

7 Sept - 8 Sept

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

A modern gym with a large window, wooden paneling, and illuminated vertical lights.

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

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

18. Emrose Luxury Cabins

Brandon

Tiffany

S$232

includes taxes & fees

15 Sept - 16 Sept

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

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

A hotel room with two beds, a large beach mural on the wall, and a wooden floor.

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

19. Days Inn by Wyndham Rutland/Killington Area

Rutland

Charlotte

S$165

includes taxes & fees

30 Aug - 31 Aug

A two-story house with a porch, surrounded by trees.

A bedroom with a large bed, two bedside tables, a small table, and a window with curtains.

A room with a high ceiling, wooden beams, and a carpeted floor. There are several wooden tables and chairs arranged for dining.

A small outdoor structure with a metal roof, a chimney, and a stack of wood.

20. Inn at Neshobe River

Brandon

Keith

S$244

includes taxes & fees

28 Aug - 29 Aug

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Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.

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Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.

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Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

See all hotels in Pittsfield

Top Pittsfield Hotel Reviews

Emrose Luxury Cabins

10/10 Excellent

"The Cabins are very nice clean and cozy , love how well they were thought out to fit everything so perfectly in a small space . Full bathroom , full kitchen and nice size refrigerator and microwave . Perfect for a romantic getaway . Plus the outdoor accommodations were great . And can’t wait for the soon to come restaurant and lounge for the guests . A++ stay . Staff were very nice and helpful"

Sleep Woodstock Motel

8/10 Good

"VERY clean and well supplies room. Didn't know about the call check-in method when we arrived, but worked out fine with a little help from another guest. Very comfortable and convenient. Thank you."

Hampton Inn Rutland

10/10 Excellent

"Excellent location and delicious breakfast! Friendly staff"

Mountain Sports Inn

8/10 Good

"basic no frills accomadation, room was clean, bed was comfy"

The Mountain Inn at Killington

10/10 Excellent

"Such a great experience and stay. We checked in as guests and left as family. The rooms were clean and comfortable, the location perfect, and the staff beyond friendly and helpful. Will definitely be returning."

The Shire Woodstock

8/10 Good

"It was a nice and cozy place to stay and experience Woodstock VT."

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good

"Food was shocking ....."

Lincoln Inn & Gallery

10/10 Excellent

"The property was very nice , very clean and comfortable. A very well kept property . We really enjoyed being able to sit on the patio and have a fire at night. The property is beautiful and set right on the river. We will definitely be back in the future ."

Comfort Inn Rutland - Killington

8/10 Good

"Enjoyed my stay. Felt safe."