Explore top 2025 4 Star Hotels in Pittsfield

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Top Pittsfield 4 Star hotels

Woodstock Inn & Resort

Fourteen The Green, Woodstock, VT

$389 nightly

$428 total

Nov 16 - Nov 17

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! (539 reviews)

"Beautiful hotel with excellent staff and room cleanliness. Red Rooster Inn had good breakfast options, however dinner was a little underwhelming and expensive. There are better options at the local fine dining restaurants."

Reviewed on Oct 18, 2025

The Jackson

43 Senior Lane, Woodstock, VT

$149 nightly

$164 total

Nov 4 - Nov 5

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! (235 reviews)

"The staff were incredible, so friendly and welcoming. Each night they served wine, cheese and crackers. The overall atmosphere and hospitality was amazing. We hated to leave."

Reviewed on Oct 7, 2025

On The River Inn

1653 West Woodstock Road, Woodstock, VT

$226 nightly

$249 total

Oct 26 - Oct 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 ...

9.2/10 Wonderful! (1,001 reviews)

"Room could be updated worn out carpet"

Reviewed on Oct 15, 2025

The Village Inn of Woodstock

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! (94 reviews)

"The owners (Heather and Jared) work extremely hard to make sure everyone enjoys their stay. Breakfast was excellent! Heather prepares a made to order breakfast for each guest every morning. We also decided to have dinner at The Vic Tavern. It's an extremely popular place so make reservations early. ..."

Reviewed on Oct 1, 2025

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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 ...

"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 White River Golf Club and Liberty Hill Farm are located nearby.

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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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Deer Brook Inn

4548 West Woodstock Road, Woodstock, VT

A restaurant, free self parking, and a fireplace in the lobby are among this bed & breakfast's amenities. Guests will appreciate free perks like continental ...

"The Inn was so lovely and charming and exceeded our expectations! The hospitality offered by the Inn Keeper and his team was truly remarkable and we felt welcome and spoiled throughout our stay. The property itself is stunning and the attention to detail is five star in our book!!! We will definitely ..."

Reviewed on Sep 22, 2019

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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 4-star 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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The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home

37 Butler Rd, Killington, VT

Free WiFi in public areas is available at this lodge. Take advantage of the free self parking.

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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.