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, PO Box 664, East Canaan, CT
2.15 km from city center
Stay at this 3-star B&B in East Canaan. Enjoy free breakfast, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
21.5 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 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
29.52 km from city center
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
30.52 km from city center
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
32.62 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 ...
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
23.32 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 ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
22.73 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 ...
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2 out of 5
492 East Main St, Torrington, CT
26.55 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 Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road, Litchfield, CT
30.62 km from city center
Stay at this 4-star spa hotel in Litchfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition ...
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road, Great Barrington, MA
26.11 km from city center
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
the Alander

the Alander

2.5 out of 5
7519 NY-22, Copake, NY
23.02 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 ...
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

2.5 out of 5
395 Winsted Rd, Torrington, CT
24.74 km from city center
Book a stay at this business-friendly hotel in Torrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
31.24 km from city center
Stay at this B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Naumkeag Museum are located ...
Blackberry River Inn

Blackberry River Inn

3 out of 5
538 Greenwoods Rd W, Norfolk, CT
3.55 km from city center
Stay at this 3-star B&B in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2 out of 5
980 Pleasant Street, Lee, MA
30.1 km from city center
Book a stay at this business-friendly motel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
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
Sat, Jun 21 - Sun, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jun 21 from Orlando Intl. to Bradley Intl., returning Sun, Sep 7, priced at $152 found 4 days ago
American Airlines
Thu, Sep 4 - Sat, Sep 6
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$170 Roundtrip, found 2 hours ago
$170
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Sep 4 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Sep 6, priced at $170 found 2 hours ago
JetBlue Airways
Sun, Jun 29 - Thu, Jul 17
TPA
Tampa Intl.
BDL
Bradley Intl.
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sun, Jun 29 from Tampa Intl. to Bradley Intl., returning Thu, Jul 17, priced at $192 found 3 days ago
Delta
Tue, Sep 9 - Tue, Sep 16
ORD
O'Hare Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 9 from O'Hare Intl. to Bradley Intl., returning Tue, Sep 16, priced at $197 found 1 day ago