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

$469 nightly

$516 total

Jun 9 - Jun 10

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! (582 reviews)

"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

On The River Inn

1653 West Woodstock Road Woodstock VT

$211 nightly

$232 total

Jun 28 - Jun 29

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! (1,000 reviews)

"We had one of the apartments out back and it was really nice. The staff was very responsive and helpful. We had dinner at the restaurant and the food was very good and the waiter, Brian I think, was a very nice deadpan comedian. We enjoyed the hot tub too! The only thing we didn't appreciate was ..."

Reviewed on May 28, 2026

The Jackson

43 Senior Lane Woodstock VT

$175 nightly

$193 total

Jun 9 - Jun 10

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! (284 reviews)

"Wonderful and quaint. We loved our stay. The only negative is that there wasn’t someone on-site to address questions when we arrived past 7pm and on Sunday."

Reviewed on Jun 4, 2026

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! (97 reviews)

"Breakfast was good. They give you a choice out of 2 of 3 things. It’s nice to have a variety, especially when staying somewhere for several days. I believe we rented the largest room, that had an attached sitting/ tv room and balcony. Well, everything was great except the bathroom was really small. ..."

Reviewed on May 28, 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! (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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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 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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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.