East Canaan Vacations from $688

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Your East Canaan Vacation

Say bye-bye to planning worries and hello to a East Canaan vacation package. With everything organized before you go, you can focus on discovering this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. Fill your schedule with visits to Haystack Mountain State Park, Land of Nod Vineyard and Winery and Campbell Falls State Park, some of the top attractions you just have to see during a trip to East Canaan. That dream East Canaan vacation is just clicks away. Explore airfares, hotels and more on Expedia for a trip that's tailored just for you.

The Latest East Canaan vacation packages

Price found within the past 48 hours. Click for updated prices.
The Hidden Inn

The Hidden Inn

4 out of 5
Save 100% on your flight
Price was $973, price is now $688 per person
$688
per person
Nov 5 - Nov 12
found 20 hours ago
Roundtrip flight included
New York (NYC) 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

Amazing Hiking Cozy Home Close to Mountns Fireplace

Amazing Hiking Cozy Home Close to Mountns Fireplace

2 out of 5
Save 100% on your flight
Price was $1,750, price is now $1,248 per person
$1,248
per person
Nov 5 - Nov 12
found 20 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Save 100% on your flight
Price was $1,053, price is now $763 per person
$763
per person
Nov 5 - Nov 12
found 20 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.2/10 Wonderful! (266 reviews)
Very convenient to hiking trails. Staff very friendly and helpful

Reviewed on Aug 23, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $2,262, price is now $1,639 per person
$1,639
per person
Nov 5 - Nov 12
found 20 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.4/10 Exceptional! (170 reviews)
Loved everything about it, especially large deck with view of waterfall. Interiors were beautiful and contemporary in a very convenient and comfortable way. No negatives.

Reviewed on Aug 18, 2025

Twin Cabin I - Hot Tub Firepit Hiking Retreat

Twin Cabin I - Hot Tub Firepit Hiking Retreat

2 out of 5
Save 100% on your flight
Price was $2,498, price is now $1,820 per person
$1,820
per person
Nov 5 - Nov 12
found 20 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews
Don't see what you're looking for?
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Discover the most popular places to visit in East Canaan

Land of Nod Vineyard and Winery

You can enjoy a tasting or tour at Land of Nod Vineyard and Winery during your travels to North Canaan. Discover the area's waterfalls and countryside.

Land of Nod Vineyard and Winery

East Canaan Hotel Deals

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3 out of 5
131 East Canaan Road, PO Box 664, East Canaan, CT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $121 total per night from Aug 25 to Aug 26
$121 total
Aug 25 - Aug 26
Total with taxes and fees
8.8/10 Excellent! (381 reviews)
Great Place
"The breakfast was amazing!!!"

Reviewed on Jul 28, 2025

Locust Tree Bed and Breakfast LLC
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! (1,002 reviews)
"Great location and close enough to walk to shops and restaurants."

Reviewed on Aug 22, 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
$220 nightly
The price is $246 total per night from Aug 27 to Aug 28
$246 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Typical issues with old properties: failing latches, old windows, broken or missing pavers. Excessive wait times. Mediocre food service at excessive prices. Pet-friendly accommodations are good and convenient. Location makes up for almost all failings."

Reviewed on Aug 20, 2025

The Red Lion Inn
See all 876 properties in East 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 an East Canaan vacation package cost?
Offering excellent value package deals from $688 on Expedia, you'll be surprised at how little a vacation to East Canaan costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to East Canaan?
If you're hoping to score a cheap East Canaan vacation package, consider visiting in January, March and December. You're likely to find lower prices on flights and accommodations during these months — ideal for a budget-friendly getaway.
How many days is enough for East Canaan?
With a well-organized travel plan, you can easily tick off the top East Canaan sights in a few days. But if you prefer to discover hidden spots or go on day tours, consider booking your East Canaan vacation for longer.
How to find the best East Canaan package deals?
Use Expedia's handy filters to help you find some of the best East Canaan package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for East Canaan package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book an East Canaan vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights individually. Better still, you can customize your East Canaan getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to East Canaan?
If you have your East Canaan travel dates confirmed, book early to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later East Canaan vacation packages?
Secure your dream getaway to East Canaan with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.