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
$186 nightly
The price is $208 total per night from Dec 14 to Dec 15
$208 total
Dec 14 - Dec 15
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 ...
9.6/10 Exceptional! (548 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.

Reviewed on Dec 7, 2025

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
$85 nightly
The price is $95 total per night from Dec 11 to Dec 12
$95 total
Dec 11 - Dec 12
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 ...
8.6/10 Excellent! (346 reviews)
The room was so big it felt like we were in an apartment to be honest. It was well worth the price we paid 😁. If your looking for a place to stay,I would definitely recommend this hotel. The front desk guy was really nice and happy to let us in with a pet for the night. Thanks again 😊🐾

Reviewed on Nov 28, 2025

Opens in a new windowThe Central Downtown Inn & Suites
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St. Lee MA
$195 nightly
The price is $218 total per night from Dec 12 to Dec 13
$218 total
Dec 12 - Dec 13
Total with taxes and fees
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! (289 reviews)
The room was very cute and very clean! We loved the staff. Everyone was beyond helpful and kind.

Reviewed on Nov 14, 2025

Opens in a new windowLakehouse Inn
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
$349 nightly
The price is $390 total per night from Dec 11 to Dec 12
$390 total
Dec 11 - Dec 12
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 ...
9.8/10 Exceptional! (134 reviews)
Room was clean and owner was personable and charming. Breakfast was beautiful.

Reviewed on Nov 27, 2025

Opens in a new windowDevonfield Inn B&B
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, ...
Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!

Reviewed on Oct 30, 2023

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Opens in a new windowSeven Hills Inn
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
$414 nightly
The price is $462 total per night from Jan 5 to Jan 6
$462 total
Jan 5 - Jan 6, 2026
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 ...
9.2/10 Wonderful! (85 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

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

33 Main

4 out of 5
33 Main Street Lenox MA
$436 nightly
The price is $488 total per night from Jan 8 to Jan 9
$488 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
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 ...
9.8/10 Exceptional! (74 reviews)
Every point of contact I had at 33 Main was friendly, efficient, and accommodating. It’s evident Donna and her team run the inn with love. It’s clean and gorgeously furnished on the inside. You’ll recognize it from the outside, because it’s the most charmingly decorated on the block. I stayed in ...

Reviewed on Oct 24, 2025

Opens in a new window33 Main
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

4 out of 5
Stockbridge MA
This vacation home features a garden, laundry facilities, and barbecue grills.
9.6/10 Exceptional! (100 reviews)
Great place! I highly recommend!

Reviewed on Nov 20, 2025

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Opens in a new windowGeneral Williams Estate House Lenox/Stockbridge
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
$263 nightly
The price is $294 total per night from Jan 1 to Jan 2
$294 total
Jan 1 - Jan 2, 2026
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 ...
8.8/10 Excellent! (43 reviews)
Comfortable bed. Quiet location. Excellent breakfast. Friendly host.

Reviewed on Nov 17, 2025

Opens in a new windowHampton Terrace Inn
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Lee MA
$263 nightly
The price is $294 total per night from Jan 1 to Jan 2
$294 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This bed & breakfast features an outdoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, ...
9.6/10 Exceptional! (99 reviews)
Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again.

Reviewed on Nov 24, 2025

Opens in a new windowThe Inn at Stockbridge
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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

The Williams Inn

The Williams Inn

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. "
A verified traveler stayed at The Williams Inn
The Williams Inn

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