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

4 Stars Hotels in Pittsfield, Vermont from CA $401

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Check availability on Pittsfield 4 Star Hotels

Tonight
Sep 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Pittsfield 4-star hotels

A room with a checkered floor, a bench, and a fireplace.
A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.
A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.
A spacious living room with a grand chandelier, large windows, and a comfortable seating area.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
Kevin
CA $730
CA $864 total
includes taxes & fees
Sep 14 - Sep 15
Woodstock Inn & Resort
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.
A two-story house with a porch, American flags, and a well-maintained garden.
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.

2. The Jackson

The Jackson
West Woodstock
United States
Yanil
CA $364
CA $401 total
includes taxes & fees
Sep 13 - Sep 14
The Jackson
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 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
CA $380
CA $448 total
includes taxes & fees
Sep 15 - Sep 16
On The River Inn
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.
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.
A room with a fireplace, a table with a teapot and cup, and a mirror above the fireplace.

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 modern living room with a large sliding glass door leading to a balcony with a mountain view.
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a dining area with a chandelier.
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 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.
A wooden table with a stack of magazines and a vase with pink flowers.

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 wooden cabin with a deck, outdoor seating, and large windows.
A bedroom with a large window offering a view of trees and a forest.
A cozy living room with a black leather sofa, wooden flooring, and a kitchen in the background.

7. Eagle Ridge Treehouse

Eagle Ridge Treehouse
Stockbridge
Eagle Ridge Treehouse
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.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.

8. 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 lodge with a dock, a pond, and a grassy area.
A spacious living room with a fireplace, a television, and a kitchen in the background.
A modern house with a covered porch, large windows, and a stone pathway.
A dining area with a wooden table, chairs, and a view of trees through large windows.

9. 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 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.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.

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 modern loft-style interior with a herringbone-patterned wooden floor, a yellow sofa, a bar area with stools, and a stone accent wall.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.

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 modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.

12. 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 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.
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.

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 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 modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.
A pool table with a blue felt surface, surrounded by blue chairs, in a room with a sloped ceiling and large windows.

15. 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.
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, and a mounted deer head.
A modern A-frame lodge with a stone exterior, large windows, and a covered front porch.

16. 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 high ceilings, 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 modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.

17. The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home

The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
Killington
The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
A parking lot with a building in the background, surrounded by greenery and mountains.
A wooden deck with a glass door leading to a snowy outdoor area.
A staircase with wooden railings leading to a bedroom with a bed and a window.
A wooden cabin with a snow-covered roof and a visible door.

18. 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 two-story building with a covered porch and a parking lot in front.
A modern kitchen with stainless steel appliances, white cabinets, and a patterned backsplash.
A modern living room with a stone fireplace, a flat-screen TV mounted above it, wooden flooring, and a kitchen area in the background.
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence and a building.

19. Killington Center 412

Killington Center 412
Killington
Killington Center 412

20. Tanglewood Blues by Killington Vacation Rentals

Tanglewood Blues by Killington Vacation Rentals
Killington
Tanglewood Blues by Killington Vacation Rentals
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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

The Jackson

The Jackson

10/10 Excellent
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Vicki 1-night trip
Posted 3 days ago
The Jackson

Find out more about Pittsfield

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Pittsfield are calling your name. Known for providing first-rate service in amazing locations, each of the Pittsfield 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Pittsfield. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Pittsfield, Vermont, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Pittsfield hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Pittsfield?
To book a 4-star hotel in Pittsfield that matches your budget, use Expedia's handy filter tool. Check out what's available during your chosen dates and use our pricing filter to set your limit. You can also list your results by the most budget-friendly property first.
  • Search for the lowest price from CA $401
What's the difference between 5-star and 4-star hotels in Pittsfield?
If you decide to vacation at a 4-star hotel in Pittsfield, you'll usually find lots of conveniences to keep you relaxed, such as a gym, restaurant and pool. You can experience high-quality service and deluxe accommodations. Choose a 5-star hotel and you'll get a few extra bells and whistles — think around-the-clock concierge, on-site spas and nightly turndown services. You'll most likely get additional amenities and first-rate services at a 5-star retreat, though both are fabulous options for luxury travellers.
Does Pittsfield have any 4-star all-inclusive resorts?
Enjoy a relaxing vacation experience where just about everything is included in one upfront price by using our "All inclusive" filter. Budgeting is a cinch when your room, food, activities and entertainment are already taken care of. Eager for more options? Browse the great deals on Expedia's standard 4-star stays in and around Pittsfield.

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