Canaan Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Canaan
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
€77
10 Nov - 11 Nov
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside ..."
Reviewed on 11 Oct 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
190 Meadow Street South Lee MA
Fully refundable
€134
14 Oct - 15 Oct
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"The room was incredible. Just need to be a little friendly at the arrival."
Reviewed on 10 Oct 2026
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
€201
3 Nov - 4 Nov
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Reviewed on 6 Oct 2026
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.
Stay near popular Canaan attractions
C H Pease Museum
This Victorian-era natural history collection showcases meticulously preserved local wildlife from the 1800s. Examine rare bird specimens and vintage taxidermy in North Canaan's historic Douglas Library.
Connecticut Railroad Historical Museum
Housed in the restored Canaan Union Station, this museum showcases the region's railway heritage through vintage artefacts. Model trains and historical photographs transport you to the golden age of rail travel.
Edith Scoville Memorial Sanctuary
Traverse lush forests to Lion's Head Peak at this tranquil Connecticut sanctuary. The challenging trail rewards hikers with panoramic views of rolling hills and vibrant fall foliage.
Douglas Library
Douglas Library, established in 1821, stands as one of Connecticut's oldest public libraries with 17,000 volumes. Browse the local history collection or join community events like storey hours and art exhibitions.
Eddy Field
Sam Eddy Field offers tennis courts and volleyball facilities in a relaxed community setting. Bring your own sports equipment and enjoy the park's proximity to the town pool for a complete recreational experience.
Lawrence Field
Lawrence Field hosts thrilling dog sport competitions for participants of all skill levels. Spectators can enjoy the vibrant atmosphere while watching remarkable displays of canine athleticism and teamwork.
Frequently asked questions
How much does a Canaan holiday package cost?
You'll find cheap prices 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 holiday to Canaan costs.
What are the cheapest months to go to Canaan?
January, February and March are the best times to search for cheap Canaan holiday packages. Travelling in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Canaan?
The ideal length of your Canaan holiday depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to visit all the top sights and discover some hidden gems 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 holiday package as soon as possible.
Is it cheaper to book a Canaan holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and accommodation separately. Better still, you can customise 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 holiday 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.
How to plan a trip to Canaan?
- Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Canaan.
- Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your hotel will likely be the largest expense during your trip to Canaan.
- Decide how long to go away for: Now that you know more about Canaan, you can figure out the ideal length of your holiday. Put together a draft plan and allocate enough time for all the things you want to do.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Canaan holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
