Explore top 2026 4 Star Hotels in Canaan

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Top Canaan 4 Star hotels

The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road Litchfield CT
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $268 total per night from Jan 25 to Jan 26
$268 total
Jan 25 - Jan 26
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! (969 reviews)
Great, warm, elegant Inn. Feels special. Will be back.

Reviewed on Jan 22, 2026

Opens in a new windowThe Litchfield Inn
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
$239 nightly
The price is $267 total per night from Feb 16 to Feb 17
$267 total
Feb 16 - Feb 17
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

Opens in a new windowDevonfield Inn B&B
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
$335 nightly
The price is $374 total per night from Feb 15 to Feb 16
$374 total
Feb 15 - Feb 16
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

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The White Hart

The White Hart

4 out of 5
15 Under Mountain Rd Salisbury CT
$272 nightly
The price is $313 total per night from Jan 29 to Jan 30
$313 total
Jan 29 - Jan 30
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! (146 reviews)
Such a cozy, authentic New England hotel, with all its charm.

Reviewed on Jan 20, 2026

Opens in a new windowThe White Hart
9 Academy

9 Academy

4 out of 5
9 Academy St Salisbury CT
$494 nightly
The price is $568 total per night from Jan 26 to Jan 27
$568 total
Jan 26 - Jan 27
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

Opens in a new window9 Academy
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

4 out of 5
Stockbridge MA
This vacation home features a garden, laundry facilities, and barbecue grills.
9.6/10 Exceptional! (105 reviews)
Very good location. Home was quite nice.

Reviewed on Jan 19, 2026

Opens in a new windowGeneral Williams Estate House Lenox/Stockbridge
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Lee MA
$251 nightly
The price is $280 total per night from Jan 26 to Jan 27
$280 total
Jan 26 - Jan 27
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

Opens in a new windowThe Inn at Stockbridge
The Old Inn On The Green

The Old Inn On The Green

4 out of 5
134 Hartsville-New Marlborough Rd Great Barrington MA
$336 nightly
The price is $368 total per night from Jan 25 to Jan 26
$368 total
Jan 25 - Jan 26
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

Opens in a new windowThe Old Inn On The Green
Rock Hall Luxe Lodging

Rock Hall Luxe Lodging

4.5 out of 5
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

Opens in a new windowRock Hall Luxe Lodging
ABC Stay - Connecticut Five Bedroom Home

ABC Stay - Connecticut Five Bedroom Home

4 out of 5
38 Strawberry Ridge Lane New Preston CT
This vacation home features a 24-hour gym and a hot tub. WiFi in public areas is free. Barbecue grills are provided for your convenience.
Opens in a new windowABC Stay - Connecticut Five Bedroom Home
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4 Star Hotels 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 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 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 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.

Recent Canaan hotel reviews by fellow wanderers