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

Pittsfield Hotel Guide - 4 Stars Hotels in Pittsfield, Vermont

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Check availability on Pittsfield 4 Star Hotels

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, (589 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
The price is Rp8.472.485
Rp10.114.594 total
includes taxes & fees
2 Aug - 3 Aug
Woodstock Inn & Resort
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,007 reviews)
The price is Rp4.272.914
Rp5.097.762 total
includes taxes & fees
13 Jul - 14 Jul
On The River Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (293 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is Rp2.910.272
Rp3.201.299 total
includes taxes & fees
22 Jul - 23 Jul
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, (98 reviews)
"Inn was beautiful, the details exactly what you'd want for a weekend getaway. Room was cozy (room 6), bed was comfortable, jetted tub was awesome for us not having a tub at home, bar was a nice place to hang out and breakfast was excellent. Location was perfect, it was an easy walk into the center of town, even in winter. Honestly, nothing bad to say."
United States
Nicholas
The Village Inn of Woodstock
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
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
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 Rp26.758.560
Rp41.256.422 total
includes taxes & fees
26 Jul - 27 Jul
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
Apartment (2 Bedrooms) | 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 Rp20.704.714
Rp31.936.970 total
includes taxes & fees
26 Jul - 27 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 Rp18.910.948
Rp30.206.986 total
includes taxes & fees
26 Jul - 27 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 Rp17.229.214
Rp27.043.467 total
includes taxes & fees
26 Jul - 27 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 Rp18.621.763
Rp28.994.496 total
includes taxes & fees
26 Jul - 27 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: 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 Rp16.108.178
Rp25.465.048 total
includes taxes & fees
26 Jul - 27 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: 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 price is Rp22.049.993
Rp34.626.761 total
includes taxes & fees
26 Jul - 27 Jul
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 #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 Rp16.444.453
Rp25.938.523 total
includes taxes & fees
26 Jul - 27 Jul
The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
House, Multiple Beds, Patio | Private kitchen | Fridge, microwave, stovetop, dishwasher

Breakaway B

Breakaway B
4.0 star property
Killington
Breakaway B
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
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 Rp19.471.466
Rp30.200.558 total
includes taxes & fees
26 Jul - 27 Jul
The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 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

10/10 Excellent
"Staff was friendly and helpful. Room was clean and amenities appreciated. Breakfast was very good, a great way to start the day."
Marcella 3-night trip
Posted 2 days ago
On The River Inn
The Jackson

The Jackson

10/10 Excellent
"My only complaint is that our television didn't work. And we told the staff member setting up the evening wine and cheese that and she said someone else had also had the problem. We had had a thunderstorm and thought that maybe that was it, and she said she would check in our room while we were gone that evening. But when we returned, the television still didn't work and there was no indication that anybody."
Martha 1-night trip
Posted 9 days ago
The Jackson

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Pittsfield?
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What's the difference between 5-star and 4-star hotels in Pittsfield?
If you decide to book a stay at a 4-star hotel in Pittsfield, you'll usually find lots of amenities to ensure you're comfortable, such as a gym, restaurant and pool. You can look forward to excellent service and upmarket surroundings. Choose a 5-star hotel and you'll have access to a few more bells and whistles — think around-the-clock concierge, on-site spas and opulent turndown services. You're likely to get extra amenities and premium services at a 5-star getaway, but both are awesome options for luxury travellers.
Does Pittsfield have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your dream resort in Pittsfield where everything is taken care of, from your accommodation to your meals, activities and entertainment. We can also help you find standard 4-star stays in and around this leading destination.