East Canaan Trips (flight + hotel)

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Top hotels in East Canaan

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
The price is P5,993 per night from Aug 18 to Aug 19
P5,993
P6,892 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (380 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
The price is P5,288 per night from Sep 1 to Sep 2
P5,288
P5,907 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The day manager was welcoming, knowledgeable and helpful. The night manager was not helpful when we called to complain that our room had not been made up for the night, nor were the used towels taken. He claimed that we had to ask for the room to be cleaned. The next morning, the day manager had ..."

Reviewed on Aug 14, 2025

Quality 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
The price is P5,223 per night from Sep 2 to Sep 3
P5,223
P6,631 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (691 reviews)
"Staff is helpful and friendly!"

Reviewed on Aug 11, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 878 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.

Popular places to visit

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

Frequently asked questions

How much does an East Canaan vacation package cost?
Offering excellent value package deals 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?
You can usually find lower rates and better availability in January, February and March. Take a look at our cheap East Canaan vacation packages and you could score some great off-season discounts.
How many days is enough for East Canaan?
With a well-organized travel plan, you can easily visit the top East Canaan attractions in a handful of days. But if you want to venture off the beaten track or go on day tours, think about 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.
How to plan a trip to East Canaan?

  1. Choose when to get away: Check your calendar and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to escape to East Canaan.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and airfares. Your hotel will likely be the largest expense during your trip to East Canaan.
  3. Decide how long to go for: Now that you're up to speed on East Canaan, you can figure out the ideal length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored East Canaan vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.