East Canaan Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3 out of 5
131 East Canaan Road East Canaan CT
1.89 km from city center
Stay at this B&B in East Canaan. Enjoy free breakfast, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
20.96 km from city center
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

3.5 out of 5
190 Meadow Street South Lee MA
29.05 km from city center
Book a stay at this ski hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
29.96 km from city center
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
24.23 km from city center
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
170 Housatonic Street Lee MA
32.08 km from city center
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 out of 5
74 Interlaken Road Lakeville CT
15.42 km from city center
Book a stay at this spa hotel in Lakeville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Holley-Williams House Museum and Gay Woods ...
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2 out of 5
492 East Main St Torrington CT
27.04 km from city center
Book a stay at this business-friendly motel in Torrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
the Alander

the Alander

2.5 out of 5
7519 NY-22 Copake NY
22.79 km from city center
Stay at this lodge in Copake. Enjoy free WiFi, free parking, and rainfall showerheads. Our guests praise the helpful staff in our reviews. Popular attractions ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3 out of 5
249 Stockbridge Rd Great Barrington MA
22.18 km from city center
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road Litchfield CT
31.17 km from city center
Book a stay at this spa hotel in Litchfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition ...
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
22.77 km from city center
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Little Cat Lodge

Little Cat Lodge

2 out of 5
37 Catamount Rd Copake Falls NY
23.76 km from city center
Stay at this hotel in Copake Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Catamount Ski Area and Catamount Aerial Adventure ...
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
25.56 km from city center
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
22.13 km from city center
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Don't see what you're looking for?
See all available properties in East 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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Dec 2 - Sat, Dec 5
DEN
Denver Intl.
BDL
Bradley Intl.
$270 Roundtrip, found 21 hours ago
$270
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Denver Intl. to Bradley Intl., returning Sat, Dec 5, priced at $270 found 21 hours ago
Breeze Airways
Thu, Nov 12 - Thu, Nov 19
TPA
Tampa Intl.
BDL
Bradley Intl.
$283 Roundtrip, found 2 days ago
$283
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Nov 12 from Tampa Intl. to Bradley Intl., returning Thu, Nov 19, priced at $283 found 2 days ago
JetBlue Airways
Sun, Dec 6 - Mon, Dec 7
DEN
Denver Intl.
BDL
Bradley Intl.
$355 Roundtrip, found 21 hours ago
$355
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Sun, Dec 6 from Denver Intl. to Bradley Intl., returning Mon, Dec 7, priced at $355 found 21 hours ago
Delta
Sat, Dec 19 - Thu, Dec 31
TPA
Tampa Intl.
BDL
Bradley Intl.
$363 Roundtrip, found 3 days ago
$363
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Dec 19 from Tampa Intl. to Bradley Intl., returning Thu, Dec 31, priced at $363 found 3 days ago
United
Sat, Dec 5 - Tue, Dec 8
DEN
Denver Intl.
BDL
Bradley Intl.
$427 Roundtrip, found 21 hours ago
$427
Roundtrip
found 21 hours ago
Select United flight, departing Sat, Dec 5 from Denver Intl. to Bradley Intl., returning Tue, Dec 8, priced at $427 found 21 hours ago