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

Hotels in Pittsfield

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Where to stay in Pittsfield?

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

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".

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 a fireplace, wooden furniture, and a television.

1. The Trailside Inn

North Sherburne

$183

$201 total

includes taxes & fees

Oct 26 - Oct 27

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

A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

2. Mountain Meadows Lodge

Killington

$142

$181 total

includes taxes & fees

Nov 8 - Nov 9

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 wooden interior with a staircase, a dining area, and a living room with a sofa and a lamp.

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.

3. Greenbrier Inn

Killington

$175

$202 total

includes taxes & fees

Oct 19 - Oct 20

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

A snow-covered road with a sign reading 'Welcome to Killington.'

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

$132

$146 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

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

5. Après Inn Killington

Killington

$138

$152 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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.

6. Snowed Inn

Killington

$127

$154 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A lodge with a fire pit, outdoor seating, and a covered area with string lights.

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

7. The Mountain Top Inn & Resort

Chittenden

$295

$322 total

includes taxes & fees

Nov 1 - Nov 2

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 spacious dining area with high ceilings and large windows, featuring wooden tables and chairs, a piano, and a view of the outside.

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

8. The Mountain Inn at Killington

Killington

$149

$172 total

includes taxes & fees

Oct 19 - Oct 20

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

A room with a wooden cabinet containing a television and a vintage-style mini-fridge.

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.

9. Killington Haus

Killington

$109

$120 total

includes taxes & fees

Oct 20 - Oct 21

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

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

10. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

$139

$152 total

includes taxes & fees

Nov 1 - Nov 2

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

11. Best Western Inn & Suites Rutland-Killington

Rutland

$161

$177 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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

An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.

12. Comfort Inn Rutland - Killington

Rutland

$118

$130 total

includes taxes & fees

Oct 25 - Oct 26

A modern bedroom with a bed, a sofa, a wooden coffee table, a TV, and a window with a view.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and tall trees.

13. The Suites at Killington Center

Killington

$132

$365 total

includes taxes & fees

Oct 20 - Oct 21

A rectangular swimming pool with a metal ladder, surrounded by white and brown lounge chairs, and a white fence.

Two white doors with numbers 131 and 132, a carpeted floor, and a plain wall.

14. Cozy Hotel Room Style Studio Condo With Pool

Killington

$118

$245 total

includes taxes & fees

Oct 20 - Oct 21

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

15. Brandon Inn

Brandon

$135

$148 total

includes taxes & fees

Nov 1 - Nov 2

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

A hotel room with a bed, a desk, a chair, a kitchenette, and a framed picture on the wall.

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.

16. My Place Hotel-Randolph VT

Randolph Center

$103

$112 total

includes taxes & fees

Nov 8 - Nov 9

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

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.

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.

17. Days Inn by Wyndham Rutland/Killington Area

Rutland

$118

$130 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

18. Sleep Woodstock Motel

Woodstock

$97

$145 total

includes taxes & fees

Nov 15 - Nov 16

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

A cozy room with a wooden bench, a chair, and a sofa. There are large windows with wooden frames and a chandelier hanging from the ceiling.

A well-maintained lawn with a central garden area, a brick building, and a view of a forested hill.

A bedroom with a large window, a bed, a chair, and a lamp.

19. The Jackson

West Woodstock

$132

$145 total

includes taxes & fees

Nov 5 - Nov 6

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

A modern kitchen with granite countertops, wooden cabinets, and a central island.

A hotel room with a large bed, a wooden headboard, two bedside tables with lamps, and a framed picture on the wall.

A large, multi-story hotel with a prominent entrance and a parking lot.

20. Hampton Inn Rutland

Rutland

$135

$149 total

includes taxes & fees

Nov 8 - Nov 9

View all properties

Go beyond your typical stay in Pittsfield

Top landmarks in Pittsfield

Pittsfield Town Hall

Pittsfield Town Hall is worth a visit when in central Pittsfield.

See properties

Roger Clark Memorial Central Library

Roger Clark Memorial Central Library is worth a visit when in central Pittsfield.

See properties

Learn more about Pittsfield

Pittsfield is well-known for its attractions such as Green Mountain National Forest and Pittsfield Town Hall.

See all hotels in Pittsfield

Check out reviews of Pittsfield hotels guests love

Mountain Meadows Lodge

Killington

10/10 Exceptional

Timothy

The Trailside Inn

North Sherburne

10/10 Exceptional

I've never wrote a review on any product or hotel until now and that is because the Trailside Inn deserves all the recognition it could get! To start, the owners Josh and Ann are fantastic. We arrived Friday night after a long drive from Long Island - we were immediately greeted by Josh who welcomed us to the lodge and took the time to show us the best trails at Killington and offered advice on restaurants near by. It was very cold Saturday so we didn't stay long at the mountain. When we...

Alyssa

Greenbrier Inn

Killington

10/10 Exceptional

KEVIN

Snowed Inn

Killington

10/10 Exceptional

Tammy

Après Inn Killington

Killington

10/10 Exceptional

Anonymous traveler

The Mountain Top Inn & Resort

Chittenden

10/10 Exceptional

We only stayed for two nights but could not have been happier! The staff was extremely helpful and friendly. The views and grounds are beautiful. We loved the beautiful, quiet setting. It rained one of the days we were at the hotel, but the staff was eager to give recommendations of places to go for other indoor activities! We were extremely pleased to visit the Mountain Top Inn and will definitely return for another stay!

Anonymous traveler

The Mountain Inn at Killington

Killington

10/10 Exceptional

Donna

North Star Lodge and Resort

Killington

10/10 Exceptional

Thayer

Killington Haus

Killington

10/10 Exceptional

Zoe

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

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

Inn at Neshobe River

Brandon

10/10 Exceptional

Anonymous traveler

Best Western Inn & Suites Rutland-Killington

Rutland

10/10 Exceptional

Judie

The Jackson

West Woodstock

10/10 Exceptional

Tiffany

Sleep Woodstock Motel

Woodstock

10/10 Exceptional

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John

Brandon Inn

Brandon

10/10 Exceptional

Shahram

A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

A wooden deck with a hot tub, a wooden chair, and a broom leaning against the wall.

A two-story house with a covered porch and a well-maintained garden.

A room with a wooden desk, a lamp, and two leather sofas with patterned cushions.

Deer Brook Inn

Woodstock

10/10 Exceptional

I highly recommend Deer Brook Inn. The photos don’t do it justice. It’s beautiful, cozy, well-kept and everything you’d want for a Vermont getaway. The innkeepers may be some of my favorite humans I’ve ever met. Their energy is bright and peaceful which reflects into the energy of the inn. They have cookies, coffee, teas and other drinks at night and a delicious custom breakfast in the morning. They have chickens out back, a fire pit and a sauna. It’s about a 7min drive from downtown Woodstock....

Lauren

A bench with snow accumulation, a fire pit with visible flames, and a wooden fence in the background.

A pool area with lounge chairs and a view of a mountainous landscape.

A sign for the Grand Hotel Spa in Killington, Vermont, with a mountain backdrop.

A reception desk with a stone wall backdrop and wooden accents, a person with a suitcase, and a television screen above the desk.

Killington Grand Hotel

Base Area

10/10 Exceptional

SUSSIE

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 spacious living room with a large American flag, a fireplace, and a chandelier.

On The River Inn

West Woodstock

10/10 Exceptional

Ayleen

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

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

A dining area with wooden chairs and tables, large windows with arched tops, and a ceiling fan.

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

The Lilac Inn

Brandon

10/10 Exceptional

Karen

Hampton Inn Rutland

Rutland

10/10 Exceptional

Anonymous traveler

Frequently Asked Questions

What accommodations do travelers recommend in Pittsfield?

Guests like The Mountain Inn at Killington, Killington Mountain Lodge, Tapestry Collection by Hilton and Mountain Meadows Lodge.

Can I book a refundable accommodation in Pittsfield?

If you need the flexibility to change your travel plans to Pittsfield, most accommodations provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Pittsfield if I want a vacation home instead of a hotel?

If you want a good alternative to a hotel, review our selection of 28 vacation homes.

What will the weather in Pittsfield be like during my trip?

The warmest months in Pittsfield are usually July and August with an average temp of 63°F. January and February are the chilliest months when the average temp is 23°F. The rainiest months are July and June.

Why should I book my Pittsfield hotel with Hotels.com?

There are plenty of reasons to book your Pittsfield travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.