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

Hotel Vienna

3 out of 5
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

Wylder Hotel Windham

3.5 out of 5
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

The Haüs Windham

2 out of 5
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

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Canaan Hotel Deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
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

The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
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

Quality Inn Great Barrington
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
$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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,019 properties in 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 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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Frequently asked questions

How much does a Canaan vacation package cost?
You'll find cheap prices from $627 on Expedia for your Canaan escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Canaan costs.
What are the cheapest months to go to Canaan?
You're likely to find reduced prices and greater availability in December, January and February. Explore our cheap Canaan vacation packages and you could get some great off-season deals.
How many days is enough for Canaan?
The ideal length of your Canaan vacation depends on what you'd like to do. Usually, a few days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures along the way.
How to find the best Canaan package deals?
Use Expedia's filter tool to help you find some of the best Canaan package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Canaan package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Canaan vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can customize your Canaan trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Canaan?
Score incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Canaan trip.
Does Expedia offer Book Now, Pay Later Canaan vacation packages?
Your Canaan getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.