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

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Check availability on Pittsfield 4 Star Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

Our top choices for Pittsfield 4-star hotels

Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (586 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
The price is 15.765.081 ₫
18.499.625 ₫ total
includes taxes & fees
9 Jul - 10 Jul
Woodstock Inn & Resort
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,004 reviews)
"Beautiful place to stay"
United States
Jeff
The price is 5.763.861 ₫
6.774.511 ₫ total
includes taxes & fees
12 Jul - 13 Jul
On The River Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (288 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is 4.974.291 ₫
5.471.720 ₫ total
includes taxes & fees
28 Jun - 29 Jun
The Jackson
Terrace/patio

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (97 reviews)
"Breakfast was good. They give you a choice out of 2 of 3 things. It’s nice to have a variety, especially when staying somewhere for several days. I believe we rented the largest room, that had an attached sitting/ tv room and balcony. Well, everything was great except the bathroom was really small. Prob why it’s not in any pictures."
United States
Julie
The Village Inn of Woodstock
Restaurant

Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
4.0 out of 10, (2 reviews)
"Clean room, elevator broken and not enough bathroom towels."
United States
Jing
Mountain Green Resort
Exterior

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The Woodstocker B&B
Rafting

Eagle Ridge Treehouse

Eagle Ridge Treehouse
4.0 star property
Stockbridge
Eagle Ridge Treehouse
Cottage, 1 Bedroom | Interior

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
4.0 star property
Killington
The price is 34.448.939 ₫
53.702.239 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
Interior

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

Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
4.0 star property
The Woods
8.0 out of 10, Very good, (1 review)
"Great property and location. Ground floor bedroom very drafty especially when windy at Killington. Made it difficult to comfortably get rest. Otherwise very nice living space. At the high end for cost for the size and location. "
United States
Craig
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
Cottage, 1 Bedroom | Living area

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
4.0 star property
Killington
The price is 26.670.622 ₫
41.595.228 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

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
4.0 star property
Killington
The price is 24.369.570 ₫
39.511.278 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
Apartment (3 Bedrooms) | Interior

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

1 Mi to Killington Resort: Townhome w/ Dry Sauna!
4.0 star property
Killington
1 Mi to Killington Resort: Townhome w/ Dry Sauna!
Cottage, 1 Bedroom | Interior

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
4.0 star property
Killington
The price is 22.208.715 ₫
35.313.477 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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
4.0 star property
Killington
The price is 24.081.597 ₫
37.950.496 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

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
4.0 star property
Killington
The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room
Cottage, 1 Bedroom | Living area

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
4.0 star property
Killington
The price is 20.764.901 ₫
33.279.973 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: Mission Room #2 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

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
4.0 star property
Killington
The price is 25.086.218 ₫
39.364.387 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
House, Multiple Beds, Patio | Private kitchen | Fridge, microwave, stovetop, dishwasher

Breakaway B

Breakaway B
4.0 star property
Killington
Breakaway B
Cottage, 1 Bedroom | Living area

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
4.0 star property
Killington
The price is 21.197.059 ₫
33.888.452 ₫ total
includes taxes & fees
12 Jul - 13 Jul
The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
House, 4 Bedrooms | Living room

Tanglewood Blues by Killington Vacation Rentals

Tanglewood Blues by Killington Vacation Rentals
4.0 star property
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

On The River Inn

On The River Inn

10/10 Excellent
"The location on the river"
Paul 3-night trip
Posted 3 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 5.471.720 ₫

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.