
Canaan Vacations from $627
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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.

Hotel Vienna
Save 100% on your flight
Price was $822, price is now $627 per person
$627
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.4/10 Exceptional! (808 reviews)
The access to the Windam Path was great. It is a lovely, easy walk by a stream and through meadows.
Reviewed on Jun 19, 2026

Wylder Hotel Windham
Save 100% on your flight
Price was $1,088, price is now $877 per person
$877
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
8.8/10 Excellent! (99 reviews)
Beautiful and spacious balcony overlooking the mountains and golf course. We loved the view from our room 521. . Great place to relax before dinner with a glass of wine/cheese.
Location is good within walking distance to a most wonderful restaurant named prominence. Highly recommend. The on site restaurant was nice too.
Biggest disadvantage was the tv as it does not have any cable and then ending up with no signal at all. Other than that it was a really great place to stay.
Reviewed on Jun 15, 2026

The Haüs Windham
Price was $1,008, price is now $874 per person
$874
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
7.6/10 Good! (29 reviews)
I stayed in the mirror cabin everything was great just prepare to have no microwave and or a burner. So you cannot cook or heat anything up. I was able to make it work by just getting stuff that can be eaten cold and then going out to dinner which was fine. Also because the cabin is mirror please note birds constantly fly into it on purpose. It was one bird that every day i was there from morning to night was hitting the glass and it did get very annoying.
Reviewed on Apr 20, 2026
Canaan Hotel Deals

The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $191 total per night from Jul 1 to Jul 2
$191 total
Jul 1 - Jul 2
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Our experience at the Red Lion Inn went beyond our expectations. The entire staff was most helpful, went above and beyond to make our stay enjoyable, and treated us as if we were the only guests staying there! The inn is magnificent and we felt we were staying in a museum! The accommodation was lovely ..."
Reviewed on Jun 20, 2026

Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
$104 nightly
The price is $116 total per night from Jun 25 to Jun 26
$116 total
Jun 25 - Jun 26
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain ..."
Reviewed on Jun 22, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Fully refundable
$152 nightly
The price is $169 total per night from Jun 23 to Jun 24
$169 total
Jun 23 - Jun 24
Total with taxes and fees
9.2/10 Wonderful! (914 reviews)
"Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet."
Reviewed on Jun 19, 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 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.



















