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Check availability on Pittsfield 4 Star Hotels

Top Pittsfield 4 Star Hotels

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (531)
"Relaxing "
The price is 10.746.066 ₫
12.976.729 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Woodstock Inn & Resort
On The River Inn
Family Suite, 2 Bedrooms | Private kitchen | Microwave

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1005)
"Great location, very quiet with good breakfast choices. "
On The River Inn
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (225)
"Great stay! "
The Jackson
The Village Inn of Woodstock
Garden

The Village Inn of Woodstock

4.0 star property
9.6 out of 10, Exceptional, (90)
"Super nice people. Would definitely stay there again. "
The Village Inn of Woodstock
The Woodstocker B&B
Exterior

The Woodstocker B&B

4.0 star property
10.0 out of 10, Exceptional, (51)
"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! "
The Woodstocker B&B
Eagle Ridge Treehouse
Terrace/patio

Eagle Ridge Treehouse

4.0 star property
Eagle Ridge Treehouse
The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Deer Brook Inn
Terrace/patio

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
"One of the best experiences I have ever had! The staff were kind, attentive, and just plain wonderful! I can't wait to return as soon as possible! This place is BEAUTIFUL inside and out! (Not to mention that the breakfast was to die for). Don't think twice- you need to stay at the Deer Brook Inn!"
Deer Brook Inn
The Birch Ridge: Mission Room #2 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: Mission Room #2 - 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
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 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

4.0 star property
The Birch Ridge: Blue Velvet Room #10 - Queen Suite In Killington, Vermont. Hot Tub. Lounge. 1 Bedroom Home
The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room
Cottage, 1 Bedroom | Interior

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

4.0 star property
The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room
Tanglewood Chalet at Killington by Killington Vacation Rentals
House, 4 Bedrooms | Exterior

Tanglewood Chalet at Killington by Killington Vacation Rentals

4.0 star property
Tanglewood Chalet at Killington by Killington Vacation Rentals
Breakaway B
House, Multiple Beds, Patio | Private kitchen | Fridge, microwave, stovetop, dishwasher

Breakaway B

4.0 star property
Breakaway B
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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

Top Pittsfield Hotel Reviews

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 10.746.066 ₫

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.