Explore top 2026 4 Star Hotels in Pittsfield

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Top Pittsfield 4 Star hotels

The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$179 nightly
The price is $197 total per night from Jul 28 to Jul 29
$197 total
Jul 28 - Jul 29
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, ...
9.6/10 Exceptional! (296 reviews)
"Staffing was basically non-existent with a machine generated welcome and check out. Property website stated “Food is a central component of every stay here at our Woodstock, VT Bed and Breakfast - and we take immeasurable pride in it. Our breakfast is a European-style breakfast…”which we assumed ..."

Reviewed on Jul 18, 2026

Opens in a new windowThe Jackson
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$239 nightly
The price is $263 total per night from Jul 26 to Jul 27
$263 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the ...
9.4/10 Exceptional! (1,001 reviews)
"We've stayed here a number of times. The rooms are spacious and the property is in a lovely setting. It's nice being close to Woodstock, but not right in the middle of the hustle and bustle. It's also easy to get to Killington from this location."

Reviewed on Jul 20, 2026

Opens in a new windowOn The River Inn
The Village Inn of Woodstock

The Village Inn of Woodstock

4 out of 5
41 Pleasant Street Woodstock VT
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi ...
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Opens in a new windowThe Village Inn of Woodstock
The Woodstocker B&B

The Woodstocker B&B

4 out of 5
61 River St Woodstock VT
A sauna is featured at this bed & breakfast, along with free self parking. Enjoy the free cooked-to-order breakfast each morning. A terrace, a garden, and a ...
10/10 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!"

Reviewed on Jan 24, 2025

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Opens in a new windowThe Woodstocker B&B
Mountain Green Resort

Mountain Green Resort

4 out of 5
133 E Mountain Rd Killington VT
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
4/10 (2 reviews)
"I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area."

Reviewed on Jan 28, 2026

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Opens in a new windowMountain Green Resort
Eagle Ridge Treehouse

Eagle Ridge Treehouse

4 out of 5
145 Olmstead Dr Stockbridge VT
Enjoy free WiFi, free parking, and concierge services. Popular attractions Liberty Hill Farm and Les Newell Wildlife Management Area are located nearby.
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Opens in a new windowEagle Ridge Treehouse
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 out of 5
37 Butler Rd Killington VT
$1,882 nightly
The price is $2,070 total per night from Jul 26 to Jul 27
$2,070 total
Jul 26 - Jul 27
Total with taxes and fees
Stay at this lodge in Killington. Enjoy free WiFi, free parking, and a pool table. Popular attractions Killington Resort and Black Dog Sports are located ...
Opens in a new windowThe Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!

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

4 out of 5
Killington VT
This apartment features an outdoor pool and a gym. Enjoy the sauna and perks like free self parking and free WiFi. Barbecue grills are provided for your ...
8/10 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."

Reviewed on Feb 21, 2025

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Opens in a new windowKillington Condo w/ Spa ~ 3 Miles to Ski Resort!
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 out of 5
37 Butler Rd Killington VT
$1,480 nightly
The price is $1,628 total per night from Jul 26 to Jul 27
$1,628 total
Jul 26 - Jul 27
Total with taxes and fees
Free WiFi in public areas is available at this lodge.
Opens in a new windowThe Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
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 out of 5
37 Butler Rd Killington VT
$1,381 nightly
The price is $1,519 total per night from Jul 26 to Jul 27
$1,519 total
Jul 26 - Jul 27
Total with taxes and fees
Free WiFi in public areas is available at this lodge.
Opens in a new windowThe Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
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4 Star Hotels Pittsfield

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Pittsfield 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Pittsfield will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Pittsfield, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

Recent Pittsfield hotel reviews by fellow wanderers

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Very clean quiet"
A verified traveler stayed at My Place Hotel-Randolph VT
My Place Hotel-Randolph VT

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