Canaan Vacation Packages 2026 from $854

Canaan flight + hotel vacation packages

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

Wylder Hotel Windham

$854

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) 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.

Top Canaan hotels deals

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$187 nightly

$209 total

May 31 - Jun 1

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 in the Berkshires by IHG

190 Meadow Street South Lee MA

Free Cancellation

$134 nightly

$149 total

May 25 - May 26

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

$85 nightly

$94 total

May 25 - May 26

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

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$102 total

May 31 - Jun 1

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.

Americas Best Value Inn Torrington CT

395 Winsted Rd Torrington CT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$149 total

May 24 - May 25

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a garden are also provided.

Parking included

Free WiFi

The Little Lion

506 Stockbridge Road Great Barrington MA

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$106 total

Jun 11 - Jun 12

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.

Popular places to visit

C H Pease Museum

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

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?

Eddy Field

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

Frequently asked questions

How much are vacation packages to Canaan?

Packages, which include flights and hotels in Canaan, start from as low as $854. 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.