North Canaan Vacations from $594

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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.

The Latest North Canaan vacation packages

Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $699, price is now $594 per person
$594
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
8.8/10 Excellent! (133 reviews)
Room super clean and beautiful property!

Reviewed on Nov 2, 2026

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Price was $6,077, price is now $4,711 per person
$4,711
per person
Dec 19 - Dec 24
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
No reviews

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Price was $3,203, price is now $2,554 per person
$2,554
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
No reviews

Windham NY Escape

Windham NY Escape

3 out of 5
Price was $892, price is now $814 per person
$814
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
10/10 Exceptional! (2 reviews)

Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $704, price is now $654 per person
$654
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
9.2/10 Wonderful! (122 reviews)
Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay.

Reviewed on Oct 20, 2026

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Stay near popular North Canaan attractions

North Canaan Town Hall

North Canaan Town Hall is just one of the places to see in North Canaan, so why not enjoy the other things to explore during your travels?
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North Canaan Hotel Deals

Blackberry River Inn

Blackberry River Inn

3 out of 5
538 Greenwoods Rd W Norfolk CT
$174 nightly
The price is $200 total per night from Nov 8 to Nov 9
$200 total
Nov 8 - Nov 9
Total with taxes and fees
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 Nov 5 to Nov 6
$121 total
Nov 5 - Nov 6
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$76 nightly
The price is $85 total per night from Nov 25 to Nov 26
$85 total
Nov 25 - Nov 26
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Office staff wonderful! Room clean but older carpet and bathroom looked dingy."

Reviewed on Nov 3, 2026

Quality Inn Great Barrington
See all 970 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 from $594 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.