
North Canaan Vacations from $474
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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.



Eastwind Windham
Price was $740, price is now $668 per person
$668
per person
Dec 11 - Dec 14
just found
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

The Haüs Windham
Price was $850, price is now $798 per person
$798
per person
Dec 11 - Dec 14
just found
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
8/10 Very Good! (39 reviews)
This stay was disappointing. The owners seem to be trying, but so many things were wrong that we wished we had stayed elsewhere.
The good: Great location for exploring the Catskills, especially in Fall, and convenient for skiing. Our Franklin Suite was spacious, beds comfortable, bathrooms remodeled, Wi-Fi good, and gym nice. Staff responded promptly to complaints.
The bad: Check-in required uploading photos and credit card information through a separate link despite booking through Hotels.com. With no front desk, finding our suite was difficult. Two junker cars blocked the signage and belonged to staff, who started them at 6:30 a.m. outside our window. One apparently had no muffler!
The room was more run-down than the photos suggested, with deferred maintenance, a hole in the ceiling from a previous leak, and sliding doors nearly impossible to open.
The “fully stocked kitchen” had one wine glass, two forks, dirty dishes, lipstick-stained glasses, and few supplies. No ice trays; we were told to buy ice. The dining table seated only four, although the suite sleeps six or more. Cleanliness was mediocre, with crumbs, dead bugs, and dirty dishes left behind. Even facial tissues were missing.
Bottom line: Staff were responsive, but cleanliness, maintenance, and attention to detail fell short. This might suit a group of guys on a casual ski weekend, but for a romantic Catskills getaway, we’d look elsewhere. Albergo Alegria or Wylder Windham, both nearby, looked much better.
Reviewed on Oct 24, 2026
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North Canaan Hotel Deals

Blackberry River Inn
538 Greenwoods Rd W Norfolk CT
$178 nightly
The price is $205 total per night from Nov 11 to Nov 12
$205 total
Nov 11 - Nov 12
Total with taxes and fees

Locust Tree Bed and Breakfast LLC
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 10 to Nov 11
$121 total
Nov 10 - Nov 11
Total with taxes and fees

Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
$76 nightly
The price is $85 total per night from Nov 29 to Nov 30
$85 total
Nov 29 - Nov 30
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"It was close to the venue and shopping. We could walk everywhere."
Reviewed on Nov 6, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















