Book Hotels in North Canaan, CT

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top North Canaan hotels

Blackberry River Inn

Blackberry River Inn

3 out of 5
538 Greenwoods Rd W, Norfolk, CT
$164 nightly
The price is $189 total per night from Sep 29 to Sep 30
$189 total
Sep 29 - Sep 30
Total with taxes and fees
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this bed & breakfast. Guests will appreciate free perks like cooked-to-order ...
"Loved everything especially Lucas and Joe💟☮️"

Reviewed on Sep 21, 2025

Opens in a new windowBlackberry River Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $178 total per night from Sep 30 to Oct 1
$178 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
"good"

Reviewed on Sep 22, 2025

Opens in a new windowFairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $154 total per night from Sep 28 to Sep 29
$154 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate ...
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area ..."

Reviewed on Sep 22, 2025

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road, Litchfield, CT
$284 nightly
The price is $327 total per night from Sep 28 to Sep 29
$327 total
Sep 28 - Sep 29
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 ...
"Comfortable beds, immaculate room. Complimentary breakfast was delicious; made to order omelets, delicious pancakes, potatoes, pastries. Beautiful facility in quaint Litchfield."

Reviewed on Sep 3, 2025

Opens in a new windowThe Litchfield Inn
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3 out of 5
131 East Canaan Road, PO Box 664, East Canaan, CT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $121 total per night from Sep 28 to Sep 29
$121 total
Sep 28 - Sep 29
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.
"Peaceful area and great staff; Thank you for the service and experience"

Reviewed on Aug 25, 2025

Opens in a new windowLocust Tree Bed and Breakfast LLC
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
$217 nightly
The price is $243 total per night from Sep 29 to Sep 30
$243 total
Sep 29 - Sep 30
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops."

Reviewed on Sep 16, 2025

Opens in a new windowThe Red Lion Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
$124 nightly
The price is $139 total per night from Sep 30 to Oct 1
$139 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Probably the nicest Holiday Inn Express we've stayed at. Clean, well-appointed rooms. Everything looks updated. And did I say clean?Really excellent coffee and generous hot breakfast. Friendly and helpful desk staff."

Reviewed on Sep 19, 2025

Opens in a new windowHoliday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Oct 9 to Oct 10
$104 total
Oct 9 - Oct 10
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. ...
"Very good"

Reviewed on Sep 22, 2025

Opens in a new windowQuality Inn
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Oct 26 to Oct 27
$104 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the express check-in. ...
"The room was very clean and tidy!"

Reviewed on Sep 20, 2025

Opens in a new windowQuality Inn
Don't see what you're looking for?
See all available properties in North Canaan
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What are the top kid-friendly hotels in North Canaan?
From carefully considered amenities to more room to move, kid-friendly hotels come with features that can help transform a regular family vacation into an extraordinary one. These North Canaan properties make getting away with little ones a snap: Locust Tree Bed and Breakfast LLC will help make your adventure the best one yet. It features a variety of nice touches, such as a picnic area and a pillowtop mattress. Also consider Fickle Fox Farm. It comes with a king bed, a travel crib and lots of opportunities to hang out as a family.
Where can I find cheap hotels in North Canaan?
At Travelocity you'll find really nice hotels in North Canaan at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near North Canaan rather than in North Canaan. We may find you even better rates, too.
How do I find the best North Canaan hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in North Canaan then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in North Canaan?
The cheapest hotel in North Canaan is $104. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in North Canaan?
There are 930 hotels in North Canaan on Travelocity.
What are the best hotels in North Canaan?
North Canaan has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in North Canaan for you!
When is the best time to visit North Canaan?
If you want the joy of a fun-filled trip in peak season, visit North Canaan during April, June and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, March and December.
When is the cheapest time to stay in North Canaan?
Based on historic data is usually the cheapest month to visit North Canaan. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in North Canaan?
There are multiple hotels in North Canaan that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to North Canaan. We have plenty of kid-friendly hotels in North Canaan to choose from on Travelocity!
Why book a hotel in North Canaan through Travelocity?
Because we have the top hotels in North Canaan! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in North Canaan on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent North Canaan hotel reviews by fellow wanderers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area is clean and comfortable. Staff were very responsive through text - which was handy. We had a little issue, but it was handled quickly. All-in-all, the whole family loved the room, had a great time at the resort, and felt welcomed by the staff. We look forward to coming back again next year. "
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity