Canaan Vacations from $804
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Your Canaan Vacation
Say bye-bye to planning hassles and hello to a Canaan vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. If taking in sights is on the agenda during your trip to Canaan, check out top attractions like Mount Riga State Park, Mount Frissell and Land of Nod Vineyard and Winery. Check out Expedia's wide range of travel options and book your ideal vacation to Canaan today.
The Latest Canaan vacation packages
Price found within the past 48 hours. Click for updated prices.
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.
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 story 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.
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.
Connecticut Railroad Historical Museum
Housed in the restored Canaan Union Station, this museum showcases the region's railroad heritage through vintage artifacts. Model trains and historical photographs transport you to the golden age of rail travel.
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.
Canaan Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
$101 nightly
$113 total
Oct 18 - Oct 19
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Staff was very friendly and helpful. The breakfast was very good with lots of tasty choices. Room was clean and comfortable. I would stay there again!"
Reviewed on Sep 20, 2026
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$213 nightly
$238 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Our dinner was ice cold and very over cooked. We were celebrating our birthday and our server barely spoke to us. Our first room had a small dirty shower the size of a closet. Our second room had a dirty bathtub and was very noisy. The Inn was preparing for a wedding that booked for the upcoming ..."
Reviewed on Sep 18, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
190 Meadow Street South Lee MA
Fully refundable
$135 nightly
$150 total
Sep 23 - Sep 24
Total with taxes and fees
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.
Find the Best Canaan Vacation Packages
Canaan Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Mount Frissell, Campbell Falls State Park and Haystack Mountain State Park |
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Frequently asked questions
How much does a Canaan vacation package cost?
You'll find cheap prices from $804 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 vacation to Canaan costs.
What are the cheapest months to go to Canaan?
You're likely to find reduced prices and greater availability in December, January and February. Explore our cheap Canaan vacation packages and you could get some great off-season deals.
How many days is enough for Canaan?
The ideal length of your Canaan vacation depends on what you'd like to do. Usually, a few days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures 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 vacation package as soon as possible.
Is it cheaper to book a Canaan vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can customize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Canaan vacation packages?
Your Canaan getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
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- Warner Theater
- Lime Rock Park
- Harney and Sons Tea Tasting Room
- Seven Hearths Museum
- Sloane-Stanley Museum
- Land of Nod Vineyard and Winery
- Burr Pond State Park
- Ames Plaza Shopping Center
- Satan's Kingdom State Recreation Area
- East Canaan Vacations
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
