Deals on vacations and trips to Canaan

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Canaan flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.
Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

2 out of 5
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. There's fun for all ages with a playground and an arcade/game room. A garden is also provided.
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. A lobby fireplace, a communal living room, and a library are also on offer.
Inn at Pine Plains

Inn at Pine Plains

3.5 out of 5
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hudson (HCC)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Top Canaan hotels deals

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Get rates
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
Pool
Kitchen
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $132 total per night
$132 total
Jul 17 - Jul 18
Total includes taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
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
Free Cancellation
Reserve now, pay when you stay
$170 nightly
The price is $190 total per night
$190 total
Jul 9 - Jul 10
Total includes taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
$257 nightly
The price is $288 total per night
$288 total
Jul 15 - Jul 16
Total includes taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa
Prospect Berkshires

Prospect Berkshires

2 out of 5
50 Prospect Lake Rd, Egremont, MA
Get rates
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free valet parking and free WiFi. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.
Pool
Pet friendly
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $132 total per night
$132 total
Jul 21 - Jul 22
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the express check-in. A restaurant, a 24-hour front desk, and express check-out are also provided.
Breakfast included
Free WiFi
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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

North Canaan Town Hall

North Canaan Town Hall is just one of the places to see in North Canaan, so why not enjoy the other things to explore during your travels?

North Canaan Town Hall

C H Pease Museum

You can spend time browsing the exhibits at C H Pease Museum during your travels in Canann Village Historic District.

C H Pease Museum

Eddy Field

Explore the great outdoors at Eddy Field, a lovely green space in North Canaan.

Eddy Field

Frequently asked questions

How much are vacation packages to Canaan?
Packages, which include flights and hotels in Canaan, start from as low as $767. Make your travel fantasies come to life and secure your dream vacation with Travelocity today.
How long should my Canaan vacation be?
Many travelers spend about 3 nights in Canaan, but it's entirely up to you. If you hope to discover all the wonderful things this destination has waiting for you, why not hang around for a few extra nights?
Where can I get the best vacation package deals for Canaan?
No matter how you like to travel, Travelocity can help you get your hands on an unbeatable Canaan package deal. All you need to do is pick and choose between our 400 air carriers and 1,000,000 properties worldwide.
Why should I purchase my Canaan vacation package with Travelocity?
Whether you're in search of the ultimate unplugged vacation or you crave the hustle and bustle of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to search through countless websites looking for the best deal --- our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available 24/7.
Can I save on my Canaan car rental if I bundle it with my hotel or flight?
With a Canaan vacation package, you can bundle your car, flight and hotel bookings and save tons. If you want to uncover the best of this fantastic location, why not head to Times Square? This famous sight is 95 mi from Canaan. With your own wheels, you'll be there before you know it.
Which airport is best for Canaan?
Many fly into Bradley Intl. Airport (BDL), 35 mi east of downtown Canaan. Others prefer Albany Intl. Airport (ALB) (55 mi away from central Canaan) or Tweed - New Haven Regional Airport (HVN) (55 mi away from central Canaan).
Where should I stay when visiting Canaan?
Many people opt to check in to the Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.. It's an excellent base for your Canaan vacation.

Photos of local treasures

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