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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
The price is CA $331 per night from Aug 20 to Aug 21
CA $331
CA $370 total
Aug 20 - Aug 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! (656 reviews)
"Our stay at The Williams Inn was amazing. The rooms were clean and beautiful, the staff was helpful and friendly, and our overall experience was superb. Would recommend 100%!"

Reviewed on Aug 18, 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 $126 per night from Sep 3 to Sep 4
CA $126
CA $141 total
Sep 3 - Sep 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 ...
8.4/10 Very good! (395 reviews)
"It was an OK place to stay to get a night’s sleep on my way through town."

Reviewed on Aug 18, 2026

Opens in a new windowThe Central Downtown Inn & Suites
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
The price is CA $523 per night from Sep 13 to Sep 14
CA $523
CA $613 total
Sep 13 - Sep 14
includes taxes & fees
Stay at this B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Lenox Arts Center are located ...
9.8/10 Exceptional! (102 reviews)
"This is an amazing place. A family-run Inn, with beautiful rooms, excellent breakfast food, and a beautifully maintained property with all the amenities I could want. I was particularly impressed with the shower, it had a massaging water flow that I have never seen before. I was also impressed with ..."

Reviewed on Aug 16, 2026

Opens in a new windowThe Inn at Stockbridge
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 $458 per night from Sep 7 to Sep 8
CA $458
CA $554 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
9.2/10 Wonderful! (114 reviews)
"Very lovely beautiful Room and property The outside pool was not available"

Reviewed on Jul 30, 2026

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 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
33 Main

33 Main

4 out of 5
33 Main Street Lenox MA
The price is CA $892 per night from Sep 16 to Sep 17
CA $892
CA $996 total
Sep 16 - Sep 17
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! (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion ..."

Reviewed on Jul 27, 2026

Opens in a new window33 Main
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 $442 per night from Sep 1 to Sep 2
CA $442
CA $534 total
Sep 1 - Sep 2
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
Hampton Terrace Inn

Hampton Terrace Inn

4 out of 5
91 Walker Street Lenox MA
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
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! (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

Opens in a new windowLakehouse Inn
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
The price is CA $540 per night from Sep 3 to Sep 4
CA $540
CA $603 total
Sep 3 - Sep 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! (140 reviews)
"The owners are so nice!!! Tha property is beautiful and the people that play the piano and sing during the day is the most relaxing and incredible experience!!!!"

Reviewed on Aug 4, 2026

Opens in a new windowDevonfield Inn B&B
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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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