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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 $276 per night from Nov 17 to Nov 18
CA $276
CA $309 total
Nov 17 - Nov 18
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! (540 reviews)
Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!

Reviewed on Nov 14, 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
The price is CA $125 per night from Nov 17 to Nov 18
CA $125
CA $140 total
Nov 17 - Nov 18
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! (343 reviews)
Was clean and had full kitchen of pot and pans and all stuff you need in a kitchen

Reviewed on Nov 11, 2025

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 $241 per night from Nov 20 to Nov 21
CA $241
CA $283 total
Nov 20 - Nov 21
includes taxes & fees
Stay at this 4-star 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! (288 reviews)
A charming inn in the center of the Berkshires.

Reviewed on Oct 29, 2025

Opens in a new windowLakehouse Inn
33 Main

33 Main

4 out of 5
33 Main Street, Lenox, MA
Stay at this 4-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Lenox Library are located ...
9.8/10 Exceptional! (73 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
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 $536 per night from Nov 30 to Dec 1
CA $536
CA $648 total
Nov 30 - Dec 1
includes taxes & fees
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
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
Seven Hills Inn

Seven Hills Inn

4 out of 5
40 Plunkett Street, Lenox, MA
Stay at this 4-star 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
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

4 out of 5
Stockbridge
Stay at this vacation home in Berkshire County. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and National ...
Great Place!
This was a great place to house our family of 12 during the weekend of our daughter’s wedding. There was plenty of space for everyone to gather. The beds were comfortable and all the bedrooms upstairs had their own bathroom - so nice! The house made our weekend extra special. Definitely ...

Reviewed on Nov 19, 2022

Opens in a new windowGeneral Williams Estate House Lenox/Stockbridge
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd., Lee, MA
Stay at this 4-star golf B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Greenock Country Club ...
9.8/10 Exceptional! (133 reviews)
Great place!!!

Reviewed on Oct 12, 2025

Opens in a new windowDevonfield Inn B&B
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street, Lee, MA
The price is CA $352 per night from Nov 20 to Nov 21
CA $352
CA $413 total
Nov 20 - Nov 21
includes taxes & fees
Stay at this 4-star B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and National Shrine of the Divine ...
9.6/10 Exceptional! (98 reviews)
We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!

Reviewed on Feb 18, 2025

Opens in a new windowThe Inn at Stockbridge
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street, Lenox, MA
Stay at this 4-star hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and Ventfort Hall Mansion ...
Beautiful historic house in a great location. Responsive owner. Great visit!

Reviewed on May 21, 2022

Opens in a new windowHampton Terrace Inn
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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