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

4 Stars Hotels in Pittsfield, Vermont from CA $374

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield 4 Star Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Pittsfield 4-star hotels

Lobby

1. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (597 reviews)
"As always - best hotel in Vermont."
United States
ben
The price is CA $813
CA $956 total
includes taxes & fees
Aug 6 - Aug 7
Woodstock Inn & Resort
Hallway

2. On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,012 reviews)
"Breakfast was fantastic, such a lovely and peaceful place to stay for a few nights"
United Kingdom
Laura
The price is CA $396
CA $466 total
includes taxes & fees
Aug 6 - Aug 7
On The River Inn
Restaurant

3. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (298 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is CA $340
CA $374 total
includes taxes & fees
Aug 13 - Aug 14
The Jackson
Terrace/patio

4. The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (99 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

5. 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

6. 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

7. Eagle Ridge Treehouse

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

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
4.0 star property
Killington
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
Apartment (2 Bedrooms) | Interior

9. 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

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

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

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
4.0 star property
Killington
The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
Cottage, 1 Bedroom | Living area

13. 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
Apartment (3 Bedrooms) | Interior

14. 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 | Living area

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
4.0 star property
Killington
The Birch Ridge: Mission Room #2 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

16. 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
4.0 star property
Killington
The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

17. 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
4.0 star property
Killington
The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

18. 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 Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

19. 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 Birch Ridge: Mission Room #4 - Queen Suite In Killington, Vermont 1 Bedroom Home
House, 4 Bedrooms | Living room

20. Tanglewood Blues by Killington Vacation Rentals

Tanglewood Blues by Killington Vacation Rentals
4.0 star property
Killington
Tanglewood Blues by Killington Vacation Rentals
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
"This is a gorgeous little inn. The check in/check out is virtual which felt a bit impersonal, but otherwise everything was good. The room is very cozy as were the common areas. There is coffee, tea, and water in the lobby at all times, and there is often a fire going as well. The porch is full of rocking chairs and there is a nice seating area next to a brook in the back yard. Also free wine and cheese each evening for guests!"
Caroline 3-night trip
Posted 9 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 $374

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.

Explore a world of travel with Expedia