Canaan Vacation Packages 2026 from $789

Canaan flight + hotel vacation packages

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

Windham NY Escape

$789

per person

Oct 15 - Oct 18

found 21 hours ago

Roundtrip flight included

Pittsburgh (PIT) to Hudson (HCC)

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

The Haüs Windham

$1,013

per person

Oct 15 - Oct 18

found 21 hours ago

Roundtrip flight included

Pittsburgh (PIT) 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.

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

$2,406

per person

Oct 15 - Oct 18

found 21 hours ago

Roundtrip flight included

Pittsburgh (PIT) 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.

Top Canaan hotels deals

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$208 nightly

$232 total

Sep 8 - Sep 9

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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

$93 nightly

$103 total

Sep 14 - Sep 15

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

Holiday Inn Club Vacations Oak 'n Spruce Resort

190 Meadow Street South Lee MA

Free Cancellation

$135 nightly

$150 total

Aug 31 - Sep 1

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 Lee - Lenox South

170 Housatonic Street Lee MA

Free Cancellation

$110 nightly

$122 total

Sep 14 - Sep 15

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

Little Cat Lodge

37 Catamount Rd Copake Falls NY

$149 nightly

$167 total

Aug 25 - Aug 26

Total with taxes and fees

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the sauna and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a garden are also on offer.

Pool

Breakfast included

The Little Lion

506 Stockbridge Road Great Barrington MA

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$140 total

Sep 1 - Sep 2

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and express check-in are also on offer.

Pet friendly

Parking included

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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

C H Pease Museum

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

See properties

Frequently asked questions

How much are vacation packages to Canaan?

Packages, which include flights and hotels in Canaan, start from as low as $789. 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.