Explore top 2026 4 Star Hotels in Pittsfield

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Top Pittsfield 4 Star hotels

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night from Mar 15 to Mar 16
$384 total
Mar 15 - Mar 16
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free ...
9.2/10 Wonderful! (566 reviews)
Amazing restaurant and attentive staff

Reviewed on Mar 4, 2026

Opens in a new windowWoodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$197 nightly
The price is $217 total per night from Mar 10 to Mar 11
$217 total
Mar 10 - Mar 11
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! (1,003 reviews)
The breakfast and staff were AMAZING! Freshly made scrambled eggs, bacon, sausage patties, french toast, waffles, Cabot yogurt with all the fixings, dry cereal, hot oatmeal, breads, muffins, danish, etc. Everything was delicious and well presented as well! Forgot to mention freshly gound coffee! ...

Reviewed on Mar 5, 2026

Opens in a new windowOn The River Inn
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$169 nightly
The price is $186 total per night from Mar 8 to Mar 9
$186 total
Mar 8 - Mar 9
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! (272 reviews)
Beautiful space and extremely comfortable

Reviewed on Mar 1, 2026

Opens in a new windowThe Jackson
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 inn, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. ...
9.6/10 Exceptional! (96 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 ...

Reviewed on Mar 2, 2026

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Opens in a new windowThe Village Inn of Woodstock
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
The Woodstocker B&B

The Woodstocker B&B

4 out of 5
61 River St Woodstock VT
$274 nightly
The price is $301 total per night from Apr 3 to Apr 4
$301 total
Apr 3 - Apr 4
Total with taxes and fees
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

Opens in a new windowThe Woodstocker B&B
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
$1,386 nightly
The price is $1,524 total per night from Mar 15 to Mar 16
$1,524 total
Mar 15 - Mar 16
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
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 sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided ...
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: 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
$1,789 nightly
The price is $1,968 total per night from Mar 15 to Mar 16
$1,968 total
Mar 15 - Mar 16
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
1 Mi to Killington Resort: Townhome w/ Dry Sauna!

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

4 out of 5
Killington VT
This apartment features an outdoor pool and a sauna. WiFi in public areas is free.
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Opens in a new window1 Mi to Killington Resort: Townhome w/ Dry Sauna!
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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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

3 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Clean and nicer than I expected. "
A verified traveler stayed at Days Inn by Wyndham Rutland/Killington Area
Days Inn by Wyndham Rutland/Killington Area

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