Canaan Vacation Packages 2026 from $630

Canaan flight + hotel vacation packages

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

Hotel Vienna

$630

per person

Sep 4 - Sep 7

found 14 hours ago

Roundtrip non-stop flight included

Tampa (TPA) 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

$819

per person

Sep 4 - Sep 7

found 14 hours ago

Roundtrip non-stop flight included

Tampa (TPA) 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

$212 nightly

$237 total

Jul 22 - Jul 23

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

$183 nightly

$205 total

Jul 15 - Jul 16

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

$101 nightly

$113 total

Aug 2 - Aug 3

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

$135 nightly

$151 total

Jul 28 - Jul 29

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

Prospect Berkshires

50 Prospect Lake Rd Egremont MA

$395 nightly

$441 total

Jul 9 - Jul 10

Total with taxes and fees

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

Little Cat Lodge

37 Catamount Rd Copake Falls NY

$169 nightly

$189 total

Jul 9 - Jul 10

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

Don't see what you're looking for?

See all available properties in Canaan

View all properties

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

Edith Scoville Memorial Sanctuary

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

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 $630. 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.