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

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Check availability on Pittsfield 4 Star Hotels

Tonight
26 Sep - 27 Sep
Tomorrow
27 Sep - 28 Sep
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Pittsfield 4-star hotels

A room with a checkered floor, a bench, and a fireplace.
A spacious room with large windows, a fireplace, and comfortable seating areas.
A spacious living room with a grand chandelier, large windows, and a comfortable seating area.
A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
Ann
17.376.606 ₫
20.257.123 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Woodstock Inn & Resort
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 bedroom with a large window, a bed, a chair, and a lamp.
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.

2. The Jackson

The Jackson
West Woodstock
United States
Laura
6.129.864 ₫
6.742.850 ₫ total
includes taxes & fees
26 Oct - 27 Oct
The Jackson
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 snow-covered roof and a front porch.
A two-story house with a balcony, surrounded by lush greenery and a pond.

3. On The River Inn

On The River Inn
West Woodstock
United Kingdom
Laura
6.155.319 ₫
7.342.331 ₫ total
includes taxes & fees
27 Oct - 28 Oct
On The River Inn
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.
A bar area with a wooden counter, various bottles, glasses, and a menu.
A large, two-story house with a snow-covered roof and a porch with string lights.
A person holding two plates of food in a kitchen.

4. The Village Inn of Woodstock

The Village Inn of Woodstock
Woodstock
United States
Sam
The Village Inn of Woodstock
A restaurant with a high ceiling and skylights, featuring a bar area with stools and a seating area with tables and chairs.
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a dining area with a chandelier.
An indoor swimming pool with a hot tub, steps leading to the pool, and a reception area with chairs.
A modern living room with a sofa, coffee table, and fireplace.

5. Mountain Green Resort

Mountain Green Resort
Killington
United States
Jing
Mountain Green Resort
A white building with green shutters, a brick chimney, and a picket fence.
A wooden table with a stack of magazines and a vase with pink flowers.
A bedroom with a wooden ceiling, a large bed, a rocking chair, and a sofa.
Two wooden chairs with red cushions on a porch with a striped rug, a small wooden table, and a view of trees and a white fence in the background.

6. The Woodstocker B&B

The Woodstocker B&B
Woodstock
United States
Kavina
The Woodstocker B&B
Two inflatable rafts on a rocky riverbank with a clear blue sky and mountains in the background.
A bedroom with a large window offering a view of trees and a forest.
A wooden cabin with a deck, outdoor seating, and large windows.
A wooden building with large windows and a visible staircase.

7. Eagle Ridge Treehouse

Eagle Ridge Treehouse
Stockbridge
Eagle Ridge Treehouse
A lodge with a dock, a pond, and a grassy area.
A dining area with a wooden table, chairs, and a view of trees through large windows.
A living room with a brown leather sofa, patterned cushions, a wooden coffee table, and a lamp. There are framed posters on the wall and a staircase leading to an upper level.
A spacious living room with a fireplace, a television, and a kitchen in the background.

8. Killington Condo w/ Spa ~ 3 Miles to Ski Resort!

Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
The Woods
United States
Craig
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.

9. The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home

The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
Killington
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.

10. The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home

The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Killington
The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.
A modern loft-style interior with a herringbone-patterned wooden floor, a yellow sofa, a bar area with stools, and a stone accent wall.

11. The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room

The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room
Killington
The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A modern living room with a stone wall, a fireplace, and a mounted deer head.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern A-frame lodge with a stone exterior, large windows, and a covered front porch.

12. The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home

The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
Killington
The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A wooden play structure and a charging station with cables, set against a snowy background.

13. The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home

The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Killington
The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
A spacious loft-style living area with high ceilings, exposed wooden beams, and large windows offering a view of the outdoors.
A modern living room with a stone wall, a fireplace, and a mounted deer head.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.
A wooden play structure and a charging station with cables, set against a snowy background.

14. The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home

The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
Killington
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.
A wooden play structure and a charging station with cables, set against a snowy background.

15. The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home

The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
Killington
The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
A spacious loft-style living area with high ceilings, exposed wooden beams, and large windows offering a view of the outdoors.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A pool table with a blue felt surface, surrounded by blue chairs, in a room with a sloped ceiling and large windows.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.

16. The Birch Ridge: Mission Room #2 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home

The Birch Ridge: Mission Room #2 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
Killington
The Birch Ridge: Mission Room #2 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.
A wooden play structure and a charging station with cables, set against a snowy background.

17. The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home

The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
Killington
The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
A two-story building with a covered porch and a parking lot in front.
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and a building.
A modern bedroom with a large bed, a stone fireplace, a flat-screen TV, and a kitchenette.
A modern kitchen with stainless steel appliances, white cabinets, and a patterned backsplash.

18. Killington Center 412

Killington Center 412
Killington
Killington Center 412
A parking lot with a building in the background, surrounded by greenery and mountains.
A staircase with wooden railings leading to a bedroom with a bed and a window.
A spacious kitchen with wooden cabinets, a stainless steel refrigerator, and a large island.
A wooden deck with a glass door leading to a snowy outdoor area.

19. 1 Mi to Killington Resort: Townhome w/ Dry Sauna!

1 Mi to Killington Resort: Townhome w/ Dry Sauna!
Killington
1 Mi to Killington Resort: Townhome w/ Dry Sauna!
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.
A modern living room with a stone wall, a fireplace, and a mounted deer head.

20. The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home

The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home
Killington
The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home
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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
A lake surrounded by autumn-colored trees and a rocky shoreline.

Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 7 days ago
On The River Inn

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Pittsfield?
With Expedia's handy search filters, landing a superb deal on a 4-star hotel in Pittsfield just got easier. Start by entering your chosen travel dates and length of your escape. Then sort the results by price and choose a hotel that best suits your budget and style.
  • Search for the lowest price from 6.742.850 ₫
What's the difference between 5-star and 4-star hotels in Pittsfield?
If you choose to holiday at a 4-star hotel in Pittsfield, you'll usually find loads of amenities to make sure you're comfortable, such as a restaurant, pool and gym. You can enjoy top-quality service and upscale accommodation. Go for a 5-star hotel and you'll get a few more bells and whistles — think on-site spas, around-the-clock concierge and indulgent turndown services. You'll most likely get more amenities and premium services at a 5-star stay, though both are great options for luxury guests.
Does Pittsfield have any 4-star all-inclusive resorts?
Enjoy a stress-free holiday experience where just about everything is included in the one upfront price by using our "All inclusive" filter. Staying within budget is a breeze when your meals, accommodation and activities are already taken care of. Want more options? Check out the terrific deals on Expedia's standard 4-star stays in and around Pittsfield too.

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