Compare Cheap Hotels in Canaan
Secret Bargains - Save an extra 10% or more on select hotels
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Cheap Canaan Hotels
The Red Lion Inn
30 Main Street Stockbridge MA
$190 nightly
The price is $212 total per night
$212 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.66 mi from city center
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Spa
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$139 nightly
The price is $155 total per night
$155 total
Dec 21 - Dec 22
Total with taxes and fees
17.18 mi from city center
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Air conditioning
Quality Inn Great Barrington
372 Main Street Great Barrington MA
$76 nightly
The price is $85 total per night
$85 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.8 mi from city center
With a stay at Quality Inn Great Barrington in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 8 minutes by foot from Housatonic River.
Breakfast included
Parking included
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd Great Barrington MA
$107 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
13.03 mi from city center
With a stay at Holiday Inn Express Hotel & Suites Great Barrington by IHG in Great Barrington, you'll be on a river, just steps from Housatonic River and a 3-minute drive from Monument Mountain Reservation.
Pool
Breakfast included
Days Inn by Wyndham Torrington
492 East Main St Torrington CT
$87 nightly
The price is $100 total per night
$100 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
18.23 mi from city center
Located in Torrington, Days Inn by Wyndham Torrington is within a 15-minute walk of Hotchkiss-Fyler House Museum and Warner Theater.
Breakfast included
Parking included
The Litchfield Inn
432 Bantam Road Litchfield CT
$274 nightly
The price is $315 total per night
$315 total
Jan 15 - Jan 16, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.49 mi from city center
Located in Litchfield, The Litchfield Inn is in the suburbs, within a 5-minute drive of White Memorial Conservation Center and Bantam Lake.
Breakfast included
Spa
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
$135 nightly
The price is $151 total per night
$151 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.65 mi from city center
A stay at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires places you in the heart of Great Barrington, within a 5-minute drive of Housatonic River Walk and Ski Butternut.
Pool
Breakfast included
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
$67 nightly
The price is $74 total per night
$74 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.62 mi from city center
With a stay at Monument Mountain Motel in Great Barrington, you'll be a 4-minute walk from Housatonic River and within a 5-minute drive of Housatonic River Walk.
Parking included
Free WiFi
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
$83 nightly
The price is $92 total per night
$92 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.21 mi from city center
With a stay at Quality Inn Lee - Lenox South in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Breakfast included
Free WiFi
Interlaken Inn & Resort
74 Interlaken Road Lakeville CT
$199 nightly
The price is $229 total per night
$229 total
Dec 21 - Dec 22
Total with taxes and fees
8.97 mi from city center
Located in Lakeville, Interlaken Inn & Resort is on a lake, within a 10-minute drive of Mount Frissell and Harlem Valley Rail Trail.
Pool
Spa
Prospect Berkshires
50 Prospect Lake Rd Egremont MA
$282 nightly
The price is $315 total per night
$315 total
Dec 22 - Dec 23
Total with taxes and fees
13.61 mi from city center
Located in Great Barrington, Prospect Berkshires is in the mountains, within a 10-minute drive of W.E.B. Du Bois Boyhood Homesite and Catamount Aerial Adventure Park.
Pool
Spa
the Alander
7519 NY-22 Copake NY
$119 nightly
The price is $133 total per night
$133 total
Dec 20 - Dec 21
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.66 mi from city center
With a stay at the Alander in Copake, you'll be within a 5-minute drive of Taconic State Park and Callan Family Care.
Pet friendly
Parking included
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.
Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.
Canaan hotels essential information
Accommodation | 997 hotels |
|---|---|
Lowest Price | $74 |
Highest Price | $315 |
Popular hotels | The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Quality Inn Great Barrington, Holiday Inn Express Hotel & Suites Great Barrington by IHG, Days Inn by Wyndham Torrington, The Litchfield Inn, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Monument Mountain Motel, Quality Inn Lee - Lenox South, Interlaken Inn & Resort, Prospect Berkshires, the Alander |
Most Recent Canaan Hotel Reviews
The Red Lion Inn
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Old time charm and hot tub under the stars"
A verified traveler stayed at The Red Lion Inn
Top Picks
Hotels
- Hotels in Daytona Beach
- Hotels in East Hampton
- Hotels in Farmington
- Hotels in Danbury
- Hotels in Virginia Beach
- Hotels in Savannah
- Hotels in Norwalk
- Hotels in Pismo Beach
- Hotels in Windsor
- Hotels in Palm Springs
- Hotels in Southington
- Hotels in East Haddam
- Hotels in Shelton
- Hotels in Palm Beach
- Hotels in Myrtle Beach
- Hotels in New Haven
- Hotels in Naugatuck
- Hotels in Honolulu
- Hotels in Berlin
- Hotels in Hartford
Flights
