North Canaan Vacations

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Your North Canaan Vacation

The best way to experience this interesting city is with a tailor-made North Canaan vacation package. Stay in the neighborhood of Canann Village Historic District, which is good for dining, culture and shopping or choose someplace else — our package deals are all about you. You'll want to take in some sights during your trip to North Canaan. Drop by major attractions such as Mount Riga State Park, Mount Frissell and Haystack Mountain State Park. Your North Canaan vacation is only clicks away. Explore airfares, hotels and more on Expedia for an adventure that's tailored to suit your style.

Discover the most popular places to visit in North Canaan

Land of Nod Vineyard and Winery

You can enjoy a tasting or tour at Land of Nod Vineyard and Winery during your travels to North Canaan. Discover the area's waterfalls and countryside.

Land of Nod Vineyard and Winery

North Canaan Hotel Deals

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 Dec 8 to Dec 9
$189 total
Dec 8 - Dec 9
Total with taxes and fees
9.2/10 Wonderful! (162 reviews)
Such kind and thoughtful customer service - above and beyond. Lovely people!

Reviewed on Nov 30, 2025

Blackberry River Inn
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3 out of 5
131 East Canaan Road East Canaan CT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $121 total per night from Dec 7 to Dec 8
$121 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (394 reviews)
We did not eat breakfast. We had to leave early, 8am. We were told breakfast will be ready between 8 and 9 am

Reviewed on Nov 17, 2025

Locust Tree Bed and Breakfast LLC
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 refundable
$145 nightly
The price is $162 total per night from Dec 7 to Dec 8
$162 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (795 reviews)
I loved the room we stayed in, it really gave a townhouse feel. It made you feel like you were staying in a real home. I just wished that the resort's activity center had more to offer in their grab and go eating area. They do not serve breakfast and their menu is very limited for lunch/dinner hours. ...

Reviewed on Dec 5, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 949 properties in North Canaan
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.

Find the Best North Canaan Vacation Packages

North Canaan Essential Information

Language
English
Currency
U.S dollars
Top Sights
Mount Frissell, Campbell Falls State Park and Haystack Mountain State Park

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Frequently asked questions

How much does a North Canaan vacation package cost?
You'll find cheap prices on Expedia for your North Canaan getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to North Canaan costs.
What are the cheapest months to go to North Canaan?
You can generally find reduced prices and greater availability in January, March and December. Explore our cheap North Canaan vacation packages and you could get some great off-season discounts.
How many days is enough for North Canaan?
Usually, a handful of days is enough to see the major attractions during your North Canaan vacation. However, if you prefer to have some time to kick back or go on day trips, consider extending your itinerary.
How to find the best North Canaan package deals?
Bagging a cheap North Canaan package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly North Canaan package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a North Canaan vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customize your North Canaan getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to North Canaan?
If you're planning a spontaneous North Canaan vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later North Canaan vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your North Canaan vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.