Canaan Vacation Packages 2026 from $906

Canaan flight + hotel vacation packages

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

Windham NY Escape

$906

per person

Oct 15 - Oct 18

found 20 hours ago

Roundtrip flight included

Dallas (DFW) to Hudson (HCC)

Luggage storage is available at this cabin. Take advantage of the free self parking.

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Save 100% on your flight

$1,904

per person

Oct 15 - Oct 18

found 20 hours ago

Roundtrip flight included

Dallas (DFW) to Hudson (HCC)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.

The Haüs Windham

$934

per person

Oct 22 - Oct 25

found 20 hours ago

Roundtrip flight included

Dallas (DFW) to Hudson (HCC)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A 24-hour gym and barbecue grills are also provided.

Top Canaan hotels deals

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$212 nightly

$237 total

Sep 23 - Sep 24

Total with taxes and fees

This historic 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. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Spa

Holiday Inn Club Vacations Oak 'n Spruce Resort

190 Meadow Street South Lee MA

Free Cancellation

$135 nightly

$150 total

Sep 14 - Sep 15

Total with 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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

$104 nightly

$116 total

Sep 15 - Sep 16

Total with 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

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

Free Cancellation

$107 nightly

$120 total

Sep 27 - Sep 28

Total with 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

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$106 total

Oct 4 - Oct 5

Total with taxes and fees

A gym is featured at this motel, along with free self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A safe deposit box is provided and the front desk is staffed around-the-clock.

Breakfast included

Parking included

The Abner Hotel

15 West St Litchfield CT

$225 nightly

$259 total

Sep 13 - Sep 14

Total with taxes and fees

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Dry cleaning, luggage storage, and concierge services are also on offer.

Breakfast included

Pet friendly

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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.

Stay near popular Canaan attractions

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?

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Frequently asked questions

How much are vacation packages to Canaan?

Packages, which include flights and hotels in Canaan, start from as low as $906. 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.