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
$217 nightly
The price is $243 total per night from Nov 11 to Nov 12
$243 total
Nov 11 - Nov 12
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 ...
9.8/10 Exceptional! (707 reviews)
"Clean, spacious rooms."

Reviewed on Oct 28, 2026

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
$99 nightly
The price is $111 total per night from Nov 1 to Nov 2
$111 total
Nov 1 - Nov 2
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! (431 reviews)
"Went from horrible to mediocre. Check in is an adventure as there is no front desk. First room left me with PTSD. Filthy floors, bed used and unmade, dirty dishes in the sink and so on. Again, no front desk, got code for another room in a different building. After lugging all my stuff to another ..."

Reviewed on Oct 27, 2026

Opens in a new windowThe Central Downtown Inn & Suites
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
$369 nightly
The price is $412 total per night from Nov 2 to Nov 3
$412 total
Nov 2 - Nov 3
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! (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."

Reviewed on Sep 14, 2026

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

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
$219 nightly
The price is $245 total per night from Nov 1 to Nov 2
$245 total
Nov 1 - Nov 2
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
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
$381 nightly
The price is $425 total per night from Nov 13 to Nov 14
$425 total
Nov 13 - Nov 14
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
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! (77 reviews)
"The breakfast was outstanding and it changed every day. You pre-ordered the night before. We had a lovely room."

Reviewed on Oct 26, 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
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
$383 nightly
The price is $428 total per night from Nov 12 to Nov 13
$428 total
Nov 12 - Nov 13
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 ...
9.6/10 Exceptional! (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."

Reviewed on Oct 20, 2026

Opens in a new windowThe Inn at Stockbridge
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

The Yankee Inn

The Yankee Inn

5 out of 5
Posted 11 hours ago
Travelocity Verified Review
"We had a wonderful stay over the weekend. Bed VERY comfortable. Quiet, except one early am with kids running in the halls! Parents issue! Breakfast was good. Several items needing to be replenished each am. Had to go and ask the girls a few times. They were in the back room eating, seemingly unaware of restocking needed items. The bar on the weekend was an extra perk! Loved Carl 💕, the bartender , quite a conversationalist. Overall beautiful location , walking path in the back was nice, in the back of the hotel."
A verified traveler stayed at The Yankee Inn
The Yankee Inn

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