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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 $362 per night from Apr 5 to Apr 6
CA $362
CA $404 total
Apr 5 - Apr 6
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! (605 reviews)
The room was lovely as was the restaurant. The place was delightful.

Reviewed on Apr 3, 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 $152 per night from Apr 5 to Apr 6
CA $152
CA $169 total
Apr 5 - Apr 6
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! (359 reviews)
Did not send check-in info via text, when I called they said they sent but never and resent, then gave me the wrong room. I booked double bed but got 1 king bed said double bed booking is not guaranteed and the rooms are sold out. However the worse part is the room is full of smoke smell so badly ...

Reviewed on Feb 21, 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 $210 per night from Apr 18 to Apr 19
CA $210
CA $247 total
Apr 18 - Apr 19
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! (297 reviews)
This place is a gem. We loved our brief stay at this charming, old-school lodge on a lake. We were welcomed with mulled cider (adult mix), brownies, and kindness by a charming hostess who turned was helpful throughout our stay. The room was clean and well appointed. We had a lovely view of Laurel ...

Reviewed on Mar 29, 2026

Opens in a new windowLakehouse 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 $431 per night from Apr 17 to Apr 18
CA $431
CA $521 total
Apr 17 - Apr 18
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 ...
9.2/10 Wonderful! (110 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
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
The price is CA $416 per night from May 3 to May 4
CA $416
CA $465 total
May 3 - May 4
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! (137 reviews)
Had a wonderful stay. The property is charming, elegant, and beautifully maintained, with a peaceful Berkshires setting. Our hosts were warm, welcoming, and made us feel right at home from the moment we arrived. Everything from the comfortable room to the thoughtful touches throughout our stay exceeded ...

Reviewed on Mar 22, 2026

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 $316 per night from Apr 4 to Apr 5
CA $316
CA $370 total
Apr 4 - Apr 5
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 $425 per night from Apr 5 to Apr 6
CA $425
CA $512 total
Apr 5 - Apr 6
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 $640 per night from Apr 9 to Apr 10
CA $640
CA $714 total
Apr 9 - Apr 10
includes taxes & fees
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Lenox Library are located ...
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
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
The price is CA $305 per night from Apr 7 to Apr 8
CA $305
CA $340 total
Apr 7 - Apr 8
includes taxes & fees
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and Ventfort Hall Mansion and Gilded ...
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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