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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 $350 per night from May 20 to May 21
CA $350
CA $391 total
May 20 - May 21
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! (627 reviews)
Staff was very helpful. Rooms were great. Unbeatable location for Williamstown (especially if you’re in town for an athletic event at Williams). Really solid breakfast with friendly and attentive wait staff. Only minor complaint is that the WiFi is not great. Other than that it was a perfect ...

Reviewed on May 10, 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 $157 per night from Jun 1 to Jun 2
CA $157
CA $175 total
Jun 1 - Jun 2
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! (365 reviews)
Beds were comfy and definitely a big space at a good price for a few people. Was concerned with cleanliness though as there were stains underneath the comforters. Curtains also need to be longer/ blacked out to totally block out the bright lights that glow all night right outside the window. In addition, ...

Reviewed on May 12, 2026

Opens in a new windowThe Central Downtown Inn & Suites
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
The price is CA $370 per night from May 18 to May 19
CA $370
CA $413 total
May 18 - May 19
includes taxes & fees
Book a stay at this golf B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Greenock Country Club ...
10/10 Exceptional! (138 reviews)
Excellent food and helpful staff

Reviewed on May 13, 2026

Opens in a new windowDevonfield Inn B&B
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 $426 per night from May 31 to Jun 1
CA $426
CA $515 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Lee MA
The price is CA $361 per night from May 21 to May 22
CA $361
CA $424 total
May 21 - May 22
includes taxes & fees
Stay at this B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Lenox Arts Center are located ...
9.8/10 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
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 ...
Opens in a new windowSeven Hills Inn
The Old Inn On The Green

The Old Inn On The Green

4 out of 5
134 Hartsville-New Marlborough Rd Great Barrington MA
The price is CA $454 per night from May 18 to May 19
CA $454
CA $548 total
May 18 - May 19
includes taxes & fees
Stay at this inn in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located ...
Opens in a new windowThe Old Inn On The Green
33 Main

33 Main

4 out of 5
33 Main Street Lenox MA
The price is CA $907 per night from May 18 to May 19
CA $907
CA $1,013 total
May 18 - May 19
includes taxes & fees
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and National Shrine of the Divine Mercy ...
10/10 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
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St. Lee MA
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! (299 reviews)
Staff wonderful, homemade breakfasts, outstanding experience!

Reviewed on Apr 12, 2026

Opens in a new windowLakehouse Inn
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
The price is CA $377 per night from May 25 to May 26
CA $377
CA $421 total
May 25 - May 26
includes taxes & fees
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and National Shrine of the Divine ...
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
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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.

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