Canaan Vacation Packages 2026 from $588

Canaan flight + hotel vacation packages

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

Hotel Vienna

$588

per person

Dec 21 - Dec 25

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) to Hudson (HCC)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.

Wylder Hotel Windham

$742

per person

Dec 21 - Dec 25

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) to Hudson (HCC)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.

Eastwind Windham

$753

per person

Dec 21 - Dec 25

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) to Hudson (HCC)

This hotel features a restaurant and 2 bars/lounges. Enjoy the sauna and perks like free self parking and free WiFi. A lobby fireplace, a communal living room, and a picnic area are also on offer.

The Haüs Windham

$1,207

per person

Dec 21 - Dec 25

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) 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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

$84 total

per night

Nov 22 - Nov 23

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

190 Meadow Street South Lee MA

Free Cancellation

$159 total

per night

Nov 1 - Nov 2

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

30 Main Street Stockbridge MA

$214 total

per night

Nov 16 - Nov 17

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

Prospect Berkshires

50 Prospect Lake Rd Egremont MA

$385 total

per night

Nov 11 - Nov 12

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

Pool

Spa

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

Free Cancellation

$103 total

per night

Nov 17 - Nov 18

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

Interlaken Inn & Resort

74 Interlaken Road Lakeville CT

$309 total

per night

Nov 27 - Nov 28

This hotel features a full-service spa, 3 outdoor tennis courts, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Spa

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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 $588. 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.