Explore top 2025 4 Star Hotels in Great Barrington

Name: The Old Inn On The Green
Price range: $368 total
Rating: 9

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Top Great Barrington 4 Star hotels

The Wick, Hudson, A Tribute Portfolio Hotel

41 Cross Street, Hudson, NY

Fully refundableReserve now, pay when you stay

$203 nightly

$229 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and ...

8.6/10 Excellent! (538 reviews)

Pretty good - nice location

"It’s decent - a marriot - cool vibe, nice room, however the hallway seemed a bit rundown, carpet slightly musty, doesn’t look as new and fresh as in the pictures but still a decent stay for the cost"

Reviewed on Sep 15, 2025

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

$102 nightly

$114 total

Nov 2 - Nov 3

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! (326 reviews)

"This large space was a welcome change after being in hotel rooms for 2 weeks! Although it's somewhat dated, we enjoyed our stay. It was wonderful to have a full kitchen with dishes, pots and pans, toaster, and coffee maker. Check in and check out was easy. A great value."

Reviewed on Oct 15, 2025

Lakehouse Inn

615 Laurel St., Lee, MA

$187 nightly

$209 total

Oct 20 - Oct 21

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! (285 reviews)

"Lovely setting on a lake. Friendly staff. Nice breakfast. Peaceful"

Reviewed on Oct 6, 2025

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

26 Glendale Road, RR 183, Stockbridge, MA

$335 nightly

$374 total

Nov 3 - Nov 4

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! (82 reviews)

"My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations ..."

Reviewed on Oct 12, 2025

The White Hart

15 Under Mountain Rd, Salisbury, CT

$296 nightly

$340 total

Oct 27 - Oct 28

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies ...

9.6/10 Exceptional! (141 reviews)

"Amazing stay. Incredible staff, attention to detail. Beyond expectations"

Reviewed on Oct 2, 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, ...

"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

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9 Academy

9 Academy St, Salisbury, CT

$444 nightly

$511 total

Oct 20 - Oct 21

Total with taxes and fees

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

8.6/10 Excellent! (7 reviews)

"The Loft was so beautifully decorated and every detail was perfect."

Reviewed on Oct 8, 2024

General Williams Estate House Lenox/Stockbridge

Stockbridge

This vacation home features a garden, laundry facilities, and barbecue grills.

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

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The Old Inn On The Green

134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA

$336 nightly

$368 total

Nov 2 - Nov 3

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 ...

9/10 Wonderful! (90 reviews)

"Beautiful Inn and outstanding chef"

Reviewed on Oct 3, 2025

Devonfield Inn B&B

85 Stockbridge Rd., Lee, MA

$379 nightly

$423 total

Nov 4 - Nov 5

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 ...

9.8/10 Exceptional! (131 reviews)

"Great place!!!"

Reviewed on Oct 12, 2025

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4 Star Hotels Great Barrington

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 Great Barrington 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 Great Barrington 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 Great Barrington, 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.