
Canaan Vacations from $621
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Your Canaan Vacation
Say bye-bye to planning hassles and hello to a Canaan vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. If taking in sights is on the agenda during your trip to Canaan, check out top attractions like Mount Riga State Park, Mount Frissell and Land of Nod Vineyard and Winery. Check out Expedia's wide range of travel options and book your ideal vacation to Canaan today.
The Latest Canaan vacation packages
Price found within the past 48 hours. Click for updated prices.

The Hidden Inn
Price was $740, price is now $621 per person
$621
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hudson (HCC)
8.8/10 Excellent! (51 reviews)
We arrived at night in time for a cocktail and an appetizer.Everything was great .Room was immaculate and quiet. Would definitely stay again if in area .
Reviewed on Oct 10, 2025

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort
Save 100% on your flight
Price was $2,877, price is now $2,056 per person
$2,056
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
10/10 Exceptional! (1 review)
We encountered issues with the kitchen lightings and dish washer. Other than that, the house is beautiful and spacious.
Reviewed on Sep 27, 2025

The Haüs Windham
Save 100% on your flight
Price was $2,828, price is now $2,142 per person
$2,142
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
8.6/10 Excellent! (15 reviews)
Hot tub could have been cleaner but all in all. Beautiful and amazing views! Great service with the front desk calls and extra towels provided no problem!
Reviewed on Sep 15, 2025


Canaan Hotel Deals

The Red Lion Inn
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $203 total per night from Nov 23 to Nov 24
$203 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
In a very nice annex suite.
Reviewed on Oct 18, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundable
$142 nightly
The price is $158 total per night from Nov 2 to Nov 3
$158 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (757 reviews)
Awesome visit to the Berkshires!
The room was spotless and a perfect fit for our needs.
Reviewed on Oct 15, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
$102 nightly
The price is $114 total per night from Nov 13 to Nov 14
$114 total
Nov 13 - Nov 14
Total with taxes and fees
8.8/10 Excellent! (678 reviews)
This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well.
Reviewed on Oct 18, 2025
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 Canaan Vacation Packages
Canaan Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
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.


















