Canaan Vacation Packages 2026 from $513

Canaan flight + hotel vacation packages

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

Hunter Lodge, a Bluebird by Lark

$513

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

New York (NYC) 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.

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

$7,021

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

New York (NYC) 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.

Woodland Zen by Avantstay Modern Design + Patio

$1,054

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

New York (NYC) to Pittsfield (PSF)

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

Deer Mountain Inn

$929

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

New York (NYC) to Hudson (HCC)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Little Cat Lodge

$785

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

New York (NYC) to Pittsfield (PSF)

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.

Top Canaan hotels deals

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

190 Meadow Street South Lee MA

Free Cancellation

$130 nightly

$145 total

Mar 28 - Mar 29

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

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$211 total

Apr 7 - Apr 8

Total with 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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$75 total

Apr 6 - Apr 7

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 Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

Free Cancellation

$107 nightly

$120 total

Mar 30 - Mar 31

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Days Inn by Wyndham Torrington

492 East Main St Torrington CT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$97 total

Mar 29 - Mar 30

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 Litchfield Inn

432 Bantam Road Litchfield CT

Free Cancellation

Reserve now, pay when you stay

$247 nightly

$284 total

Mar 26 - Mar 27

Total with taxes and fees

A full-service spa and a 24-hour gym are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like cooked-to-order breakfast and free self parking.

Breakfast included

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.

Popular places to visit

Edith Scoville Memorial Sanctuary

Explore the great outdoors at Edith Scoville Memorial Sanctuary, a lovely green space in North Canaan.

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?

Frequently asked questions

How much are vacation packages to Canaan?

Packages, which include flights and hotels in Canaan, start from as low as $513. 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.