Explore top 2026 4 Star Hotels in Cummington

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Top Cummington 4 Star hotels

The Williams Inn

101 Spring Street Williamstown MA

$174 nightly

$194 total

Nov 4 - Nov 5

Total with taxes and fees

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

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$99 nightly

$111 total

Oct 12 - Oct 13

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 ...

8.4/10 Very Good! (422 reviews)

"The staff were helpful and the room was clean. Overall the experience was good"

Reviewed on Oct 4, 2026

The Inn at Stockbridge

30 East Street Stockbridge MA

$383 nightly

$428 total

Nov 1 - Nov 2

Total with taxes and fees

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

9.6/10 Exceptional! (107 reviews)

"Great property. Disappointed the pool wasn't clean despite having pool towels available."

Reviewed on Sep 22, 2026

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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Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

$369 nightly

$412 total

Nov 2 - Nov 3

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! (141 reviews)

"Wonderful location and hosts are amazing. Breakfast was great. Clean."

Reviewed on Sep 14, 2026

Hampton Terrace Inn

91 Walker Street Lenox MA

$283 nightly

$316 total

Oct 27 - Oct 28

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

33 Main

33 Main Street Lenox MA

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! (76 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

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Lakehouse Inn

615 Laurel St. Lee MA

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! (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

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Family-friendly Hancock Home: Walk to Slopes!

Hancock MA

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and barbecue grills. ...

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4 Star Hotels Cummington

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 Cummington 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 Cummington 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 Cummington, 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 Cummington hotel reviews by fellow wanderers

Berkshire Mountain Lodge

5 out of 5

Posted 4 hours ago

Travelocity Verified Review

"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"

A verified traveler stayed at Berkshire Mountain Lodge