Canaan Vacations from $459

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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.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Save 100% on your flight
Price was $611, price is now $459 per person
$459
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.2/10 Wonderful! (266 reviews)
The staff was incredible and so helpful!! I can honestly say I haven't had such super customer service as we experienced here! Thank you

Reviewed on Aug 22, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
Price was $1,031, price is now $702 per person
$702
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9/10 Wonderful! (411 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

The Hidden Inn

The Hidden Inn

4 out of 5
Save 100% on your flight
Price was $870, price is now $628 per person
$628
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.4/10 Exceptional! (37 reviews)
The staff was great. There has to be a better communication between the hotel and expedia.

Reviewed on Aug 20, 2025

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Save 100% on your flight
Price was $782, price is now $610 per person
$610
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.2/10 Wonderful! (737 reviews)
Nice quiet place, very kind staff.

Reviewed on Aug 15, 2025

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3 out of 5
Save 100% on your flight
Price was $1,063, price is now $833 per person
$833
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
No reviews
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Canaan Hotel Deals

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Sep 7 to Sep 8
$104 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"nice place"

Reviewed on Aug 18, 2025

Quality Inn
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
$206 nightly
The price is $231 total per night from Sep 7 to Sep 8
$231 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
"Very clean, fantastic staff, comfortable bed, robes to use gping to the pool/jacuzzi, plus the large bottles of water in the room."

Reviewed on Aug 14, 2025

The Red Lion Inn
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 refundableReserve now, pay when you stay
$104 nightly
The price is $116 total per night from Sep 2 to Sep 3
$116 total
Sep 2 - Sep 3
Total with taxes and fees
9/10 Wonderful! (701 reviews)
"This place is it's own oasis in the Berkshires. Very nice place which was clean and the folks we talked to at the front desk were very very nice and helpful! It would be tough for someone who has any mobility issues, no elevator and even we had a really hard time getting into and out of the tub/shower ..."

Reviewed on Aug 22, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 979 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.

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Frequently asked questions

How much does a Canaan vacation package cost?
You'll find cheap prices from $459 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.