Explore top 2026 4 Star Hotels in Pittsfield

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Top Pittsfield 4 Star hotels

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$449 nightly

$494 total

Sep 7 - Sep 8

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 ...

9.4/10 Exceptional! (602 reviews)

"Beautiful as is the town"

Reviewed on Sep 3, 2026

The Jackson

43 Senior Lane Woodstock VT

$180 nightly

$198 total

Sep 7 - Sep 8

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! (312 reviews)

"We had a lovely 1 night stay at the quaint Jackson. We enjoyed the wine & cheese hour, had dinner at Oakes & Evelyn (on site but not part of the hotel) and enjoyed a nightcap on the porch. The bed was super comfortable, sheets were clean and crisp, robes were Frette and products smelled great. The ..."

Reviewed on Sep 4, 2026

On The River Inn

1653 West Woodstock Road Woodstock VT

$280 nightly

$308 total

Sep 10 - Sep 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 ...

The Village Inn of Woodstock

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 ...

9.6/10 Exceptional! (101 reviews)

"Friendly and helpful staff. Central location walkable to shops and grocery stores. While being on main road, it can be a bit noisy with traffic. The inn is decorated in what I call “ Unique Victorian” The food is outstanding! Breakfast is delicious and served promptly (with a smile). Important to ..."

Reviewed on Aug 19, 2026

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Mountain Green Resort

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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The Woodstocker B&B

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! (52 reviews)

"This was a wonderful experience - the room was amazing, the amenities (in-room sauna) - spectacular, the location was perfect, the breakfast delicious & the owners - gracious & welcoming!"

Reviewed on Aug 23, 2026

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Eagle Ridge Treehouse

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

37 Butler Rd Killington VT

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 ...

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

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

37 Butler Rd Killington VT

Free WiFi in public areas is available at this lodge.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

5 out of 5

Posted 2 hours ago

Travelocity Verified Review

"The staff was polite, helpful and kind even after we arrive at 2 am. The parking was clean, well illuminated, spacious and safe. From the lobby to the elevator, stairs and room all were clean. The room areas (bathroom, bed area, and kitchen) were clean and comfortable. The beds were perfect and helped us to rest and achieved the perfect night sleep after 7 hrs of travel and 8 hrs of moving my daughter bag to her dorm. The location of the hotel was perfect and accessible."

A verified traveler stayed at My Place Hotel-Randolph VT