East Canaan Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your East Canaan Holiday

With every last detail organised before you take off, our East Canaan holiday packages mean you can focus more on letting the good times roll. Whether you're staying in the neighbourhood of Winchester, which is good for nature, or someplace else, this fun city promises a world of discoveries. Every trip to East Canaan needs a well-crafted itinerary. Fill yours with leading attractions like Land of Nod Vineyard and Winery, Haystack Mountain State Park and Campbell Falls State Park. Whatever your travel plans or budget, organising a tailored East Canaan holiday is a piece of cake with Expedia.

East Canaan Holiday

East Canaan Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Mohawk Mountain Ski Area, Mohawk Mountain State Forest and Mount Frissell

Our pick of the best 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
The price is AU$192 per night from 31 Mar to 1 Apr
AU$192
includes taxes & fees
31 Mar - 1 Apr
8.8/10 Excellent! (356 reviews)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."

Reviewed on 28 Jan. 2025

Locust Tree Bed and Breakfast LLC
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
The price is AU$234 per night from 31 Mar to 1 Apr
AU$234
includes taxes & fees
31 Mar - 1 Apr
9/10 Wonderful! (613 reviews)
"Clean and great location"

Reviewed on 28 Mar. 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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
The price is AU$280 per night from 14 Apr to 15 Apr
AU$280
includes taxes & fees
14 Apr - 15 Apr
8.8/10 Excellent! (1,002 reviews)
"Great place if you’re a history buff"

Reviewed on 27 Mar. 2025

The Red Lion Inn
See all 830 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does an East Canaan holiday package cost?
Offering excellent value package deals on Expedia, you’ll be surprised at how little a holiday 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 holiday packages and you could score some great off-season discounts.
How many days is enough for East Canaan?
With a well-organised 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 holiday 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 holiday package well in advance.
Is it cheaper to book an East Canaan holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking hotels and flights individually. Better still, you can customise 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 holiday 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 holiday package.

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