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

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22 Aug - 23 Aug
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23 Aug - 24 Aug
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Our top choices for Pittsfield hotels

Hotel
Reserve now, pay later
Breakfast included
Pet-friendly
Pool
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 cozy living room with a stone fireplace, wooden furniture, and a television.
A cozy living room with wooden furniture, a fireplace, and a television.

1. The Trailside Inn

The Trailside Inn
North Sherburne
United States
Niall
฿5,204
฿5,725 total
includes taxes & fees
25 Aug - 26 Aug
The Trailside Inn
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 hotel entrance with a covered walkway, stone pillars, and a sign reading "Haywood Inn."
A modern lounge area with orange upholstered chairs, a fireplace, and large windows offering a view of autumn trees.

2. Hampton Inn Rutland

Hampton Inn Rutland
Rutland
United States
Tarsha
฿4,282
฿4,711 total
includes taxes & fees
30 Aug - 31 Aug
Hampton Inn Rutland
A calm lake surrounded by autumn-colored trees and a clear blue sky.
A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.
A room with wooden cabinets, potted plants, and hanging light fixtures.
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

Mountain Meadows Lodge
Killington
United States
Barry
฿4,981
฿6,296 total
includes taxes & fees
24 Aug - 25 Aug
Mountain Meadows Lodge
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 cozy living room with a stone fireplace, leather sofa, and a patterned rug.
A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.

4. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
United States
Kristen
฿10,618
฿11,573 total
includes taxes & fees
24 Aug - 25 Aug
The Mountain Top Inn & Resort
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 modern hotel lobby with a blue sofa, a round coffee table, and abstract art on the walls.
An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.

5. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
United States
Mancione
฿3,695
฿4,065 total
includes taxes & fees
30 Aug - 31 Aug
Comfort Inn Rutland - Killington
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 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.
A modern hotel lobby with a dining area, stone wall, and a view of the outside.

6. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
Rutland
United States
Alex
฿5,292
฿5,821 total
includes taxes & fees
30 Aug - 31 Aug
Best Western Inn & Suites Rutland-Killington
A building with a modern design, featuring large windows and a covered outdoor seating area.
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.
A swimming pool surrounded by snow, with a building in the background.

7. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
United States
Travis
฿4,381
฿5,060 total
includes taxes & fees
9 Sept - 10 Sept
The Mountain Inn at Killington
A table with a checkered placemat, a red vase with greenery and berries, and a clear plastic bag with items.
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.
A sign for Greenbrier Inn and a gift shop, with a snow-covered ground.
A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

8. Greenbrier Inn

Greenbrier Inn
Killington
United States
David
฿5,508
฿6,348 total
includes taxes & fees
23 Aug - 24 Aug
Greenbrier Inn
A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.
A modern kitchen with a granite countertop, a built-in oven, and a bar area with stools.
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.

9. Mountain Sports Inn

Mountain Sports Inn
Killington
United States
Davis
฿3,561
฿3,917 total
includes taxes & fees
23 Aug - 24 Aug
Mountain Sports Inn
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.

10. My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
Randolph Center
United States
Joey
฿4,815
฿5,248 total
includes taxes & fees
6 Sept - 7 Sept
My Place Hotel-Randolph VT
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 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.

11. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
United States
Joseph
฿5,331
฿5,864 total
includes taxes & fees
9 Sept - 10 Sept
Killington Mountain Lodge, Tapestry Collection by Hilton
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 snow-covered road with a sign reading 'Welcome to Killington.'
A multi-story building with a pool and a covered patio area.

12. North Star Lodge and Resort

North Star Lodge and Resort
Killington
United States
Jessica
฿3,881
฿4,269 total
includes taxes & fees
9 Sept - 10 Sept
North Star Lodge and Resort
An indoor swimming pool with a high ceiling, multiple ceiling fans, and a seating area with chairs and tables.

13. Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
Rutland
United States
Douglas
฿3,881
฿4,269 total
includes taxes & fees
30 Aug - 31 Aug
Days Inn by Wyndham Rutland/Killington Area
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.
A long corridor with tables and chairs, large windows, and a ceiling fan.

14. Brandon Inn

Brandon Inn
Brandon
Canada
Michael
฿4,927
฿5,419 total
includes taxes & fees
23 Aug - 24 Aug
Brandon Inn
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 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.

15. Snowed Inn

Snowed Inn
Killington
United States
Rebecca
฿4,149
฿5,020 total
includes taxes & fees
25 Aug - 26 Aug
Snowed Inn
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 sign for a hotel named 'Après Inn' in Killington, VT, indicating a vacancy.
A room with a bed, a wooden wall-mounted bike rack, a microwave, a coffee maker, and a small refrigerator.

16. Après Inn Killington

Après Inn Killington
Killington
United States
Margaret
฿4,508
฿4,959 total
includes taxes & fees
27 Aug - 28 Aug
Après Inn Killington
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 large, two-story house with a well-maintained lawn and garden.
A reception area with a decorative elephant sculpture, a framed picture, a clock, and a vase with flowers.

17. The Lilac Inn

The Lilac Inn
Brandon
United States
Kymberly
฿7,808
฿8,589 total
includes taxes & fees
14 Sept - 15 Sept
The Lilac Inn
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 golf cart on a golf course with a sign that reads "BREWER WINERY".
A small outdoor structure with a metal roof, a chimney, and a stack of wood.

18. Inn at Neshobe River

Inn at Neshobe River
Brandon
United States
Keith
฿5,717
฿6,289 total
includes taxes & fees
24 Aug - 25 Aug
Inn at Neshobe River
A modern bedroom with a curved wall, a bed, a sofa, a small table with flowers, and a walk-in closet.
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.
A modern living room with a sofa, two round tables, a fireplace, and a television.

19. Emrose Luxury Cabins

Emrose Luxury Cabins
Brandon
United States
Katie
฿5,293
฿5,981 total
includes taxes & fees
23 Aug - 24 Aug
Emrose Luxury Cabins
A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.
A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.
A modern kitchen with a wooden dining table, stainless steel appliances, and a view of the outdoors through the window.
A hotel room with two beds, a desk, and a chair. The room has a wooden floor and red walls with framed pictures.

20. Sleep Woodstock Motel

Sleep Woodstock Motel
Woodstock
United States
Sean
฿2,529
฿2,782 total
includes taxes & fees
24 Aug - 25 Aug
Sleep Woodstock Motel
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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.
See properties

Pittsfield Town Hall

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

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

Top Pittsfield Hotel Reviews

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Mountain Inn at Killington and Emrose Luxury Cabins. 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?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington 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 40 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, Roger Clark Memorial Central Library and Pittsfield Town Hall. You'll also find Liberty Hill Farm and Green Mountain National Golf Course 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.

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