Explore top 2026 4 Star Hotels in Pittsfield

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Top Pittsfield 4 Star hotels

The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $204 total per night from Sep 15 to Sep 16
$204 total
Sep 15 - Sep 16
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference ...
Opens in a new windowThe Williams Inn
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$98 nightly
The price is $110 total per night from Oct 5 to Oct 6
$110 total
Oct 5 - Oct 6
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on ...
8.4/10 Very Good! (410 reviews)
"It was priced well. The central location was convenient. The space inside was much larger than usual. There was a bedroom, living room and dining room combo with a full kitchen. It appears that it was an apartment at one time."

Reviewed on Sep 7, 2026

Opens in a new windowThe Central Downtown Inn & Suites
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
$396 nightly
The price is $442 total per night from Sep 14 to Sep 15
$442 total
Sep 14 - Sep 15
Total with taxes and fees
This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free ...
9.8/10 Exceptional! (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"

Reviewed on Aug 30, 2026

Opens in a new windowThe Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
The price is $399 total per night from Sep 28 to Sep 29
$399 total
Sep 28 - Sep 29
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seven Hills Inn

Seven Hills Inn

4 out of 5
40 Plunkett Street Lenox MA
This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free on-the-go breakfast each morning. A terrace, a garden, ...
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Opens in a new windowSeven Hills Inn
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
$409 nightly
The price is $457 total per night from Sep 14 to Sep 15
$457 total
Sep 14 - Sep 15
Total with taxes and fees
An outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi ...
10/10 Exceptional! (140 reviews)
"The owners are so nice!!! Tha property is beautiful and the people that play the piano and sing during the day is the most relaxing and incredible experience!!!!"

Reviewed on Aug 4, 2026

Opens in a new windowDevonfield Inn B&B
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
$220 nightly
The price is $246 total per night from Sep 21 to Sep 22
$246 total
Sep 21 - Sep 22
Total with taxes and fees
This hotel features an outdoor tennis court and a seasonal outdoor pool. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free ...
9/10 Wonderful! (44 reviews)
"Hot tub in the cottage was wonderful. The provided guide was very comprehensive and we appreciated all the amenities available in the main and carriage house."

Reviewed on Mar 3, 2026

Opens in a new windowHampton Terrace Inn
33 Main

33 Main

4 out of 5
33 Main Street Lenox MA
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A lobby fireplace, a communal living ...
10/10 Exceptional! (76 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion ..."

Reviewed on Jul 27, 2026

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Opens in a new window33 Main
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St. Lee MA
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A terrace, a snack bar/deli, and a ...
9.6/10 Exceptional! (303 reviews)
"Our stay at the Lakehouse was fabulous--even though a cold and rainy weekend in May. I want to return to be able to take advantage of the kayaks on the beautiful Lake Laurel! Everything was perfect: lovely room, delicious breakfast, great location near Melville's house at Pittsfield and the Hancock ..."

Reviewed on Jun 22, 2026

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Opens in a new windowLakehouse Inn
Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!

4 out of 5
Hancock MA
This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and barbecue grills. ...
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Opens in a new windowFamily-friendly Hancock Home: Walk to Slopes!
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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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

5 out of 5
Posted 10 hours ago
Travelocity Verified Review
"My go-to place for visiting NW MA."
A verified traveler stayed at Vacation Village in the Berkshires
Vacation Village in the Berkshires

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