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Featured The Berkshires 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
The price is CA $258 per night from Mar 11 to Mar 12
CA $258
CA $289 total
Mar 11 - Mar 12
includes taxes & fees
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (573 reviews)
A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff.

Reviewed on Feb 7, 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
The price is CA $148 per night from Mar 3 to Mar 4
CA $148
CA $166 total
Mar 3 - Mar 4
includes taxes & fees
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located ...
8.6/10 Excellent! (355 reviews)
Checked in was easy, instructions were easy to follow. Only one staff member but he was very responsive to issues/concern. We booked 2 rooms but one room was on another building and it was outdated. Rooms were cleaned but there was this musty smell on the hallway. Overall, good stay, close to 2 ski ...

Reviewed on Feb 2, 2026

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

Lakehouse Inn

4 out of 5
615 Laurel St. Lee MA
The price is CA $194 per night from Feb 28 to Mar 1
CA $194
CA $228 total
Feb 28 - Mar 1
includes taxes & fees
Book a stay at this beach B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.6/10 Exceptional! (292 reviews)
Warm welcome. Very clean and well presented rooms. Delicious breakfast. Highly recommended.

Reviewed on Dec 8, 2025

Opens in a new windowLakehouse Inn
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
Book a stay at this golf B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Greenock Country Club and Berkshire Mountain Country ...
9.8/10 Exceptional! (135 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
Stay at this hotel in Lenox. Enjoy free breakfast, free parking, and a garden. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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

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
The price is CA $421 per night from Mar 2 to Mar 3
CA $421
CA $510 total
Mar 2 - Mar 3
includes taxes & fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum ...
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
The price is CA $554 per night from Feb 25 to Feb 26
CA $554
CA $619 total
Feb 25 - Feb 26
includes taxes & fees
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Lenox Library and The Bookstore are located nearby.
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
Stay at this vacation home in Berkshire County. Enjoy private pools, a garden, and laundry facilities. Popular attractions National Shrine of the Divine Mercy ...
9.6/10 Exceptional! (105 reviews)
Very good location. Home was quite nice.

Reviewed on Jan 19, 2026

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
The price is CA $299 per night from Feb 18 to Feb 19
CA $299
CA $333 total
Feb 18 - Feb 19
includes taxes & fees
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ventfort Hall Mansion and Gilded Age Museum and The Bookstore ...
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
The price is CA $326 per night from Feb 22 to Feb 23
CA $326
CA $382 total
Feb 22 - Feb 23
includes taxes & fees
Stay at this B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and Berkshire Theatre Festival ...
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 The Berkshires

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 The Berkshires 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 The Berkshires 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 The Berkshires, 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 The Berkshires hotel reviews by fellow wanderers