Deals on vacations and trips to Canaan

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Canaan flight + hotel vacation packages

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

The Hidden Inn

4 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Coldbrook Bed and Breakfast

Coldbrook Bed and Breakfast

4 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
This bed & breakfast features free WiFi in public areas, a virtual front desk, and free self parking. Enjoy the free self-serve breakfast each morning. A terrace, a garden, and a picnic area are also on offer.
Cortland by Avantstay Charming Heritage Estate w/ Private Lake & Pool

Cortland by Avantstay Charming Heritage Estate w/ Private Lake & Pool

3.5 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Hudson (HCC)
An outdoor pool, free self parking, and concierge services are featured at this cottage. WiFi in public areas is free. Barbecue grills are provided for your convenience.
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Hudson (HCC)
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.

Top Canaan hotels deals

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $104 total per night
$104 total
Sep 1 - Sep 2
Total includes 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 in the Berkshires by IHG

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

3.5 out of 5
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $116 total per night
$116 total
Sep 2 - Sep 3
Total includes 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

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
$227 nightly
The price is $254 total per night
$254 total
Aug 27 - Aug 28
Total includes 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
The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road, Litchfield, CT
Free Cancellation
Reserve now, pay when you stay
$280 nightly
The price is $322 total per night
$322 total
Aug 24 - Aug 25
Total includes 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
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $122 total per night
$122 total
Sep 1 - Sep 2
Total includes 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
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Free Cancellation
$124 nightly
The price is $139 total per night
$139 total
Sep 1 - Sep 2
Total includes 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
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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

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?

North Canaan Town Hall

Edith Scoville Memorial Sanctuary

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

Edith Scoville Memorial Sanctuary

Eddy Field

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

Eddy Field

Frequently asked questions

How much are vacation packages to Canaan?
Packages, which include flights and hotels in Canaan, start from as low as $296. 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.

Photos of local treasures

Browse Canaan vacation photos for more inspiration