Hotels in Pittsfield

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Where to stay 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 hotels consistently deliver on quality, location and traveler experience. Last updated on October 22, 2026.

A stone fireplace with a sign above it reading "Trailside Lodge."

A cozy living room with a fireplace, wooden furniture, 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".

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

1. The Trailside Inn

North Sherburne

CNY1,221

CNY1,343 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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.

2. Greenbrier Inn

Killington

CNY1,168

CNY1,346 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

3. Mountain Meadows Lodge

Killington

CNY947

CNY1,209 total

includes taxes & fees

Nov 10 - Nov 11

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.

4. Mountain Sports Inn

Killington

CNY728

CNY800 total

includes taxes & fees

Nov 22 - Nov 23

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

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

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

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

5. The Mountain Top Inn & Resort

Chittenden

CNY1,969

CNY2,147 total

includes taxes & fees

Nov 1 - Nov 2

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

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

A bar area with a star sign, bicycles, and a patterned carpet.

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

6. North Star Lodge and Resort

Killington

CNY789

CNY867 total

includes taxes & fees

Oct 28 - Oct 29

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

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

7. Snowed Inn

Killington

CNY848

CNY1,026 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 lobby with a stone wall, wooden staircase, and a reception desk.

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

8. The Mountain Inn at Killington

Killington

CNY895

CNY1,034 total

includes taxes & fees

Oct 25 - Oct 26

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.

9. Après Inn Killington

Killington

CNY921

CNY1,013 total

includes taxes & fees

Oct 25 - Oct 26

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

A spacious lobby with leather seating, a stone fireplace, and a staircase leading to an upper level.

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

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

10. Killington Grand Hotel

Base Area

CNY1,550

CNY1,819 total

includes taxes & fees

Oct 23 - Oct 24

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.

11. Best Western Inn & Suites Rutland-Killington

Rutland

CNY1,076

CNY1,183 total

includes taxes & fees

Nov 2 - Nov 3

A large, red, L-shaped building with multiple windows and a snow-covered roof, surrounded by a snowy landscape and mountains in the background.

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

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

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

12. Killington Haus

Killington

CNY727

CNY800 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

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

13. Comfort Inn Rutland - Killington

Rutland

CNY790

CNY869 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A two-story house with a porch, American flags, and a well-maintained garden.

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

14. The Jackson

West Woodstock

CNY822

CNY905 total

includes taxes & fees

Nov 16 - Nov 17

A house with a red roof, a porch with white railings, and a blue door.

A white building with black shutters, a number '5763' above the entrance, and a porch with white railings and potted plants.

A wooden dining table with a woven tray, a vase with dried flowers, a small potted plant, and two candles.

A living room with a sofa, armchair, coffee table, bookshelf, and a ceiling fan.

15. Woodbridge Inn

Woodstock

CNY3,305

CNY3,635 total

includes taxes & fees

Oct 23 - Oct 24

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

CNY914

CNY1,005 total

includes taxes & fees

Nov 1 - Nov 2

A large estate with a main building surrounded by a well-maintained lawn and a river.

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

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

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

17. On The River Inn

West Woodstock

CNY1,089

CNY1,332 total

includes taxes & fees

Nov 15 - Nov 16

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

A modern kitchen with wooden cabinets, a coffee machine, and a toaster.

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

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

18. Hampton Inn Rutland

Rutland

CNY902

CNY993 total

includes taxes & fees

Nov 1 - Nov 2

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 compact living space with a kitchenette, a dining area, and a bedroom.

19. The Suites at Killington Center

Killington

CNY1,517

CNY3,137 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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

20. Brandon Inn

Brandon

CNY898

CNY988 total

includes taxes & fees

Nov 1 - Nov 2

View all properties

Go beyond your typical stay in Pittsfield

Pet friendly

Apartment

Pool

Family friendly

Hot tub

Condo

Cottage

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

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

Check out reviews of Pittsfield hotels guests love

Emrose Luxury Cabins

10/10 Excellent

"The cabin was super clean , hot tub was great just make sure to call in ahead of time if you want it set up for a specific time for a fee $35 not bad at all . Really enjoyed my stay will be back soon"

Days Inn by Wyndham Rutland/Killington Area

8/10 Good

"Tous était parfait , seulement il avait pas d’eau chaud ."

The Jackson

10/10 Excellent

"Quaint and elegant property. Thebinsite restaurant was great. Enjoyed our 1 night stay here at The Jackson."

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"Very good hotel and nice staff"

Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"Queen deluxe rooney suite is indeed a spacious, clean 920sq ft. Request for additional pillows and sheetté for 6 people was promptly met Great hotel for group"

Econo Lodge Rutland City near Hwy 7

8/10 Good

"I asked the girl at check-in for a first-floor room with 2 double beds. I am handicapped in a wheelchair, and she got us exactly what we wanted. Very clean room. Only one light in the room, so kind of on the dim side. The bed was too soft for me. The location was located to all kinds of stores and restaurants. They accept dogs for a small fee, which was great for us and our beloved Harleyquinn. Breakfast was supposed to be between 7 a.m.- 10 a.m., but at 7:15 am when I went to check out, the lobby was not open yet. I believe the worst thing is the parking. I do believe there is more in the back, but the front was pretty packed. I had to wait a few minutes for a truck to move so I could park in front of my room. Would stay here again, especially the price of the room."

Frequently asked questions

How much does a hotel room cost in Pittsfield?

You can discover great hotels in Pittsfield from CNY672 with properties to suit all budgets and needs. To find an affordable hotel in Pittsfield that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".

How can I find deals and earn rewards at Pittsfield hotels?

Discover great deals on Pittsfield hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Pittsfield hotels.

Can I book Pittsfield hotels with free cancellation?

It's easy to book a refundable Pittsfield hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some top pet-friendly hotels in Pittsfield?

Consider one of our travelers' favorite pet-friendly hotels in Pittsfield:

Clear River Inn: An inn with a guest rating of 8.8 out of 10

You can check "Pet friendly" on the Hotels.com "Amenities" filter in your search to find even more pet-friendly hotels in Pittsfield.

What are some of the best Pittsfield hotels with free parking?

If you're exploring by car, finding a great Pittsfield hotel with free parking is a win. Our travelers' favorites include:

Clear River Inn: An inn with an average guest rating of 8.8 out of 10

What are some popular hotels in central Pittsfield?

If you're looking for hotels in central Pittsfield, check out Clear River Inn. Travelers love Clear River Inn for its location, as well as the restaurant, bar/lounge and nightclub this inn offers. North Sherburne is a central neighborhood for your Pittsfield vacation.

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.

Keep exploring

Book Hotels in Pittsfield on Hotels.com