Explore top 2026 4 Star Hotels in East Canaan

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

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Top East Canaan 4 Star hotels

The Litchfield Inn

432 Bantam Road Litchfield CT

Fully refundableReserve now, pay when you stay

$220 nightly

$253 total

Dec 18 - Dec 19

Total with taxes and fees

A full-service spa and a 24-hour gym are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...

9/10 Wonderful! (957 reviews)

Quiet and so much space to lounge around in front of fireplaces. Relaxing private & was just the perfect get away!

Reviewed on Dec 2, 2025

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

$349 nightly

$390 total

Dec 10 - Dec 11

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! (134 reviews)

Room was clean and owner was personable and charming. Breakfast was beautiful.

Reviewed on Nov 27, 2025

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

26 Glendale Road, RR 183 Stockbridge MA

$414 nightly

$462 total

Jan 5 - Jan 6, 2026

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! (85 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

The White Hart

15 Under Mountain Rd Salisbury CT

$254 nightly

$292 total

Dec 10 - Dec 11

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! (143 reviews)

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

Reviewed on Oct 2, 2025

9 Academy

9 Academy St Salisbury CT

$494 nightly

$568 total

Dec 16 - Dec 17

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 ...

9/10 Wonderful! (10 reviews)

The apartment was spotless. The interior was high end with attention to design. The toiletries high end. The location was everything. Would love to go back.

Reviewed on Nov 5, 2025

General Williams Estate House Lenox/Stockbridge

Stockbridge MA

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

9.6/10 Exceptional! (100 reviews)

Great place! I highly recommend!

Reviewed on Nov 20, 2025

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The Inn at Stockbridge

30 East Street Lee MA

$263 nightly

$294 total

Jan 1 - Jan 2, 2026

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, ...

9.6/10 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

The Old Inn On The Green

134 Hartsville-New Marlborough Rd Great Barrington MA

$336 nightly

$368 total

Dec 10 - Dec 11

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

Rock Hall Luxe Lodging

19 Rock Hall Road Winsted CT

This bed & breakfast features an outdoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...

Rock Hall

The innkeepers were extememly accomadating. They made dinner reservations for us and offered suggestions of activities. Breakfast was fantastic. Before we left, we picked apples from the onsite orchard. Highly reccomended.

Reviewed on Oct 20, 2010

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4 Star Hotels East Canaan

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 East Canaan 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 East Canaan 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 East Canaan, 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.