East Canaan Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in East Canaan

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
Fully refundableReserve now, pay when you stay
The price is S$156 per night from 1 Oct to 2 Oct
S$156
1 Oct - 2 Oct
includes taxes & fees
8.8/10 Excellent! (385 reviews)
"Peaceful area and great staff; Thank you for the service and experience"

Reviewed on 25 Aug, 2025

Locust Tree Bed and Breakfast LLC
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
Fully refundableReserve now, pay when you stay
The price is S$199 per night from 28 Sept to 29 Sept
S$199
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (735 reviews)
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area ..."

Reviewed on 22 Sept, 2025

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

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is S$285 per night from 30 Sept to 1 Oct
S$285
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops."

Reviewed on 16 Sept, 2025

The Red Lion Inn
See all 879 properties in East Canaan
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

Land of Nod Vineyard and Winery

You can enjoy a tasting or tour at Land of Nod Vineyard and Winery during your travels to North Canaan. Discover the area's waterfalls and countryside.

Land of Nod Vineyard and Winery

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.