𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Pittsfield from RM415 (2026) - Fully Refundable Options

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

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Our top choices for Pittsfield hotels

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

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

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, a white sofa, a coffee table with candles, and a bag with the text "Love is All Around".

1. The Trailside Inn

North Sherburne

Marc

RM746

RM821 total

includes taxes & fees

26 Oct - 27 Oct

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.

2. Greenbrier Inn

Killington

Jeff

RM714

RM823 total

includes taxes & fees

24 Oct - 25 Oct

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

Kathy

RM579

RM739 total

includes taxes & fees

8 Nov - 9 Nov

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 modern kitchen with a granite countertop, a built-in oven, and a bar area with stools.

4. Mountain Sports Inn

Killington

Andrew

RM445

RM490 total

includes taxes & fees

22 Nov - 23 Nov

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

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.

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

5. The Mountain Top Inn & Resort

Chittenden

Allison

RM1,204

RM1,312 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

6. North Star Lodge and Resort

Killington

SUSAN

RM482

RM530 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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.

7. Snowed Inn

Killington

Melissa

RM518

RM627 total

includes taxes & fees

25 Oct - 26 Oct

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

8. The Mountain Inn at Killington

Killington

Petra

RM506

RM584 total

includes taxes & fees

29 Oct - 30 Oct

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.

9. Killington Grand Hotel

Base Area

robert

RM948

RM1,112 total

includes taxes & fees

24 Oct - 25 Oct

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

10. Après Inn Killington

Killington

Kylie

RM563

RM619 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

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

11. Best Western Inn & Suites Rutland-Killington

Rutland

Bryce

RM657

RM723 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

12. Killington Haus

Killington

Ivan

RM444

RM489 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

13. Comfort Inn Rutland - Killington

Rutland

krishna

RM483

RM531 total

includes taxes & fees

25 Oct - 26 Oct

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

14. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

Richard

RM569

RM626 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

15. Emrose Luxury Cabins

Brandon

Karol

RM735

RM830 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

16. Hampton Inn Rutland

Rutland

Brent

RM552

RM607 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

17. The Suites at Killington Center

Killington

RM927

RM1,918 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

18. Brandon Inn

Brandon

Amelia

RM549

RM604 total

includes taxes & fees

1 Nov - 2 Nov

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.

19. The Jackson

West Woodstock

Ava

RM503

RM553 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

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

20. On The River Inn

West Woodstock

SARAH

RM666

RM814 total

includes taxes & fees

15 Nov - 16 Nov

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Stay near popular Pittsfield attractions

Pittsfield Town Hall

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

See properties

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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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

The Mountain Inn at Killington

10/10 Excellent

"Friendly staff, breakfast was pretty typical for a hotel."

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent

"Good trip"

Après Inn Killington

10/10 Excellent

"Very quite, comfortable bed"

Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"clean, staff welcoming, and breakfast was solid."

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"

North Star Lodge and Resort

10/10 Excellent

"We found this lodge to be the perfect last minute stay while passing through Killington. The front desk attendant was very helpful , room perfect . Had everything we needed. Great restaurant next door also."

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."

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT

RM380

RM415 total

22 Nov - 23 Nov

includes taxes & fees

Mountain Sports Inn

813 Killington Road Killington VT

RM445

RM490 total

22 Nov - 23 Nov

includes taxes & fees

North Star Lodge and Resort

78 Weathervane Dr Killington VT

RM482

RM530 total

29 Oct - 30 Oct

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Days Inn by Wyndham Rutland/Killington Area

401 US-7 Rutland VT

RM482

RM530 total

25 Oct - 26 Oct

includes taxes & fees

7/10 Good! (1,005 reviews)

Comfort Inn Rutland - Killington

19 Allen St Rutland VT

RM483

RM531 total

25 Oct - 26 Oct

includes taxes & fees

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

RM506

RM584 total

29 Oct - 30 Oct

includes taxes & fees

9.2/10 Wonderful! (1,012 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 9.8 mi (15.8 km) from the heart of Pittsfield, The Mountain Inn at Killington is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Woodstock Inn & Resort and Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Pittsfield.

If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?

Yes, you'll find most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

What's the best dog-friendly accommodation option in Pittsfield?

Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.

What are some accommodation options with pools in Pittsfield?

The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool and free self parking. Woodstock Inn & Resort and Emrose Luxury Cabins are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.

How is it to stay in Pittsfield?

Visitors can enjoy all that Pittsfield has to offer, including the bars and restaurants. This city also attracts tourists with its welcoming locals. In Pittsfield, there are 34 hotels and other accommodation options to choose from. Find out more about Pittsfield.

What are the top places to visit in Pittsfield?

Favourite places to visit include Green Mountain National Forest, Pittsfield Town Hall and Roger Clark Memorial Central Library. You'll also find Green Mountain National Golf Course and Gifford Woods State Park in the area. Take a look at what more there is to see and do in Expedia's Pittsfield guide.

What's the seasonal weather in Pittsfield?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -5°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.

Pittsfield hotels from RM415

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Pittsfield

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Pittsfield hotels

1. The Trailside Inn

2. Greenbrier Inn

3. Mountain Meadows Lodge

4. Mountain Sports Inn

5. The Mountain Top Inn & Resort

6. North Star Lodge and Resort

7. Snowed Inn

8. The Mountain Inn at Killington

9. Killington Grand Hotel

10. Après Inn Killington

11. Best Western Inn & Suites Rutland-Killington

12. Killington Haus

13. Comfort Inn Rutland - Killington

14. Killington Mountain Lodge, Tapestry Collection by Hilton

15. Emrose Luxury Cabins

16. Hampton Inn Rutland

17. The Suites at Killington Center

18. Brandon Inn

19. The Jackson

20. On The River Inn

Stay near popular Pittsfield attractions

Pittsfield Town Hall

Roger Clark Memorial Central Library

Learn more about Pittsfield

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

Days Inn by Wyndham Rutland/Killington Area

Après Inn Killington

Best Western Inn & Suites Rutland-Killington

The Jackson

Killington Mountain Lodge, Tapestry Collection by Hilton

North Star Lodge and Resort

Econo Lodge Rutland City near Hwy 7

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

Mountain Sports Inn

North Star Lodge and Resort

Days Inn by Wyndham Rutland/Killington Area

Comfort Inn Rutland - Killington

The Mountain Inn at Killington

Frequently asked questions

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