North Canaan Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in North Canaan

Blackberry River Inn

Blackberry River Inn

3 out of 5
538 Greenwoods Rd W, Norfolk, CT
The price is 4.331.937 ₫ per night from 2 Sept to 3 Sept
4.331.937 ₫
4.981.727 ₫ total
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (127 reviews)
"The Inn is on a lovely piece of property with trees, grass, flowers. The bathroom was beautiful, the bed was comfortable and there was a common area "living room" that had a fridge for guests to place things and a microwave. The pool is fabulous (though it could use some more chaise lounges, there ..."

Reviewed on 17 Aug 2025

Blackberry River Inn
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 2.767.590 ₫ per night from 26 Aug to 27 Aug
2.767.590 ₫
3.182.729 ₫ total
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (381 reviews)
Great Place
"The breakfast was amazing!!!"

Reviewed on 28 Jul 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 2.442.069 ₫ per night from 7 Sept to 8 Sept
2.442.069 ₫
2.727.791 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Great location and close enough to walk to shops and restaurants."

Reviewed on 22 Aug 2025

Quality Inn
See all 928 properties in North 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.

Frequently asked questions

How much does a North Canaan holiday package cost?
You'll find cheap prices on Expedia for your North Canaan getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to North Canaan costs.
What are the cheapest months to go to North Canaan?
You can usually find lower rates and greater availability in January, February and March. Explore our cheap North Canaan holiday packages and you could get some great off-season deals.
How many days is enough for North Canaan?
With a well-planned itinerary, you can easily tick off the top North Canaan sights in a few days. But if you prefer to discover lesser-known spots or go on day trips, think about booking your North Canaan holiday for longer.
How to find the best North Canaan package deals?
Bagging a cheap North Canaan package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly North Canaan package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a North Canaan holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customise your North Canaan getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to North Canaan?
If you're planning a spontaneous North Canaan holiday, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to North Canaan?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite time of year and the activities on offer will also help you decide when to holiday in North Canaan.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will likely be the biggest expense during your trip to North Canaan.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in North Canaan. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored North Canaan holiday package.