Explore top 2026 4 Star Hotels in The Berkshires

Name: Garden Gables Inn
Rating: 9.2

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Top The Berkshires 4 Star hotels

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$109 nightly

$122 total

Mar 9 - Mar 10

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on ...

8.6/10 Excellent! (358 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

Lakehouse Inn

615 Laurel St. Lee MA

$139 nightly

$155 total

Mar 14 - Mar 15

Total with taxes and fees

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A terrace, a snack bar/deli, and a ...

9.6/10 Exceptional! (294 reviews)

Friendly staff, great location, beautiful views, cozy room.

Reviewed on Mar 5, 2026

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

$335 nightly

$374 total

Mar 21 - Mar 22

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...

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

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

$329 nightly

$367 total

Mar 9 - Mar 10

Total with taxes and fees

An outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi ...

10/10 Exceptional! (136 reviews)

Room was great, staff was awesome, amenities were cool

Reviewed on Feb 16, 2026

The Inn at Stockbridge

30 East Street Lee MA

$263 nightly

$294 total

Apr 3 - Apr 4

Total with taxes and fees

This bed & breakfast features an outdoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, ...

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

33 Main

33 Main Street Lenox MA

$469 nightly

$524 total

Mar 15 - Mar 16

Total with taxes and fees

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A lobby fireplace, a communal living ...

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

Seven Hills Inn

40 Plunkett Street Lenox MA

This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free on-the-go breakfast each morning. A terrace, a garden, ...

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The Old Inn On The Green

134 Hartsville-New Marlborough Rd Great Barrington MA

$336 nightly

$368 total

Mar 9 - Mar 10

Total with taxes and fees

This inn features a restaurant, a seasonal outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free ...

9.2/10 Wonderful! (90 reviews)

Beautiful Inn and outstanding chef

Reviewed on Oct 3, 2025

Hampton Terrace Inn

91 Walker Street Lenox MA

$307 nightly

$343 total

Mar 29 - Mar 30

Total with taxes and fees

This hotel features an outdoor tennis court and a seasonal outdoor pool. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free ...

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

Garden Gables Inn

135 Main St Lenox MA

A seasonal outdoor pool, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like cooked-to-order breakfast ...

9.2/10 Wonderful! (57 reviews)

Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again.

Reviewed on Feb 6, 2022

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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

The Yankee, Trademark Collection by Wyndham

5 out of 5

Posted 14 hours ago

Travelocity Verified Review

" The overall property was clean and well kept the pool and Hot Tub are very nice. The breakfast was excellent. The room we stayed in was clean. Beds were comfortable however the room was a little dated."

A verified traveler stayed at The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

3 out of 5

Posted 2 days ago

Travelocity Verified Review

"Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand because there was trash leftover from the previous person. It's basically a rental home. Maybe I missed a description but do not expect this to be your standard hotel type setting. Also, request a second floor room. We had someone above us who sounded like they were wearing their ski boots, thumping around the entire room non stop, through midnight and then restarted again at 6am. The hotel did not do any thing. We got zero sleep our last night and this entire experience has left a sour taste in my mouth. Outside of the convenience of the location, there is zero reason to really want to come back... you can't beat the price but don't expect anything but the basics. "

A verified traveler stayed at Vacation Village in the Berkshires

Berkshire Mountain Lodge

3 out of 5

Posted 3 days ago

Travelocity Verified Review

"The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after our reservation. We had purchased cancellation insurance. When we arrived a day late I asked the front desk about a refund. They told me to call Expedia, which I did. Expedia tried to reach the hotel and was unable to do so. They referred me back to the the manager. It is now a week later and after several calls to the hotel, the manager never returned my call. I find this unacceptable."

A verified traveler stayed at Berkshire Mountain Lodge