Beginning of main content

Compare Cheap Hotels in Canaan

Secret Bargains - Save an extra 10% or more on select hotels

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Get more for your budget and save up to 50% off select Secret Bargain hotels

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Get even more value with CheapTickets Price Guarantee!

Find your next hotel with our new search tool: Vacation Value Finder

Find your next hotel with our new search tool: Vacation Value Finder

Tonight
This weekend
Jan 31 - Feb 2
Next weekend
Feb 7 - Feb 9

Cheap Canaan Hotels

Price for 1 night 2 adults*

Seven Hills Inn

Seven Hills Inn

40 Plunkett Street, Lenox, MA
    4.0 out of 5.0
     
     

    Located in Lenox, Seven Hills Inn is within a 10-minute drive of Tanglewood Music Center and Lee Prime Outlets.

    $109

    Per night/room

    Jan 30 - Jan 31

    Yankee Suites Extended Stay

    Yankee Suites Extended Stay

    20 W Housatonic St., Pittsfield, MA
      4.0 out of 5.0
       
       

      With a stay at Yankee Suites Extended Stay in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Museum.

      $80

      Per night/room

      Jan 30 - Jan 31

      The Barrington

      The Barrington

      281 Main St., Level 3, Great Barrington, MA
        4.0 out of 5.0
         
         

        Located in Great Barrington, The Barrington is within a 15-minute drive of Ski Butternut and Mission House.

        $259

        Per night/room

        Jan 30 - Jan 31

        33 Main

        33 Main

        33 Main Street, Lenox, MA
          4.0 out of 5.0
           
           

          With a stay at 33 Main, you'll be centrally located in Lenox, within a 5-minute drive of Tanglewood Music Center and Lenox Library.

          $269

          Per night/room

          Feb 6 - Feb 7

          Lakehouse Inn

          Lakehouse Inn

          615 Laurel St., Lee, MA
            4.0 out of 5.0
             
             

            With a stay at Lakehouse Inn in Lee, you'll be on the beach, within a 10-minute drive of Tanglewood Music Center and Animagic Museum of Animation.

            $150

            Per night/room

            Feb 2 - Feb 3

            Garden Gables Inn

            Garden Gables Inn

            135 Main St, Lenox, MA
              4.0 out of 5.0
               
               

              With a stay at Garden Gables Inn in Lenox, you'll be in the historical district, within a 5-minute drive of Tanglewood Music Center and Lenox Library.

              $199

              Per night/room

              Feb 6 - Feb 7

              Stockbridge Country Inn

              Stockbridge Country Inn

              26 Glendale Road, RR 183, Stockbridge, MA
                4.5 out of 5.0
                 
                 

                With a stay at Stockbridge Country Inn in Stockbridge, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Chesterwood.

                Stockbridge Country InnGet Rates

                The Inn at Stockbridge

                The Inn at Stockbridge

                30 East Street, Stockbridge, MA
                  4.0 out of 5.0
                   
                   

                  With a stay at The Inn at Stockbridge in Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Theatre Festival.

                  The Inn at StockbridgeGet Rates

                  Hampton Terrace Inn

                  Hampton Terrace Inn

                  91 Walker Street, Lenox, MA
                    4.0 out of 5.0
                     
                     

                    With a stay at Hampton Terrace Inn in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Ventfort Hall Mansion and Gilded Age Museum.

                    $199

                    Per night/room

                    Jan 31 - Feb 1

                    The Old Inn On The Green

                    The Old Inn On The Green

                    134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA
                      4.0 out of 5.0
                       
                       

                      Located in Great Barrington, The Old Inn On The Green is a 5-minute drive from Dry Hill and 7 minutes from Questing.

                      $260

                      Per night/room

                      Jan 30 - Jan 31

                      Devonfield Inn B&B

                      Devonfield Inn B&B

                      85 Stockbridge Rd., Lee, MA
                        4.0 out of 5.0
                         
                         

                        With a stay at Devonfield Inn B&B in Lee, you'll be next to a golf course, within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

                        $179

                        Per night/room

                        Jan 30 - Jan 31

                        1862 Seasons on Main Bed and Breakfast

                        1862 Seasons on Main Bed and Breakfast

                        47 Main Street, Stockbridge, MA
                          4.5 out of 5.0
                           
                           

                          With a stay at 1862 Seasons on Main Bed and Breakfast in Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ski Butternut.

                          1862 Seasons on Main Bed and BreakfastGet Rates

                          Map

                          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.

                          Most Recent Canaan Hotel Reviews

                          CheapTickets Verified Review
                          4 out of 5
                          The folks at the front desk are exceptional Very friendly and helpful

                          A verified traveler stayed at Yankee Inn

                          Posted 5 months ago
                          Open Yankee Inn hotel guest reviews
                          CheapTickets Verified Review
                          5 out of 5
                          Easy and friendly check in. Very comfortable room and bed. Nice property and pool.

                          A verified traveler from Bondville vt stayed at Lantern House Motel

                          Posted 6 months ago
                          Open Lantern House Motel hotel guest reviews
                          CheapTickets Verified Review
                          3 out of 5
                          Ok. It was clean but the staff/ manager called the day before asked if we needed all 3 rooms. I told him NO. We only needed 2 of the 3. This was in time for the cancellation clause. When i checked in he gave me 3 keys. I told him NO, we had talked and cancelled. He said i would need to have called expedia to do that. I didn't book with them. He would not cancel it and was very gruff and rude.

                          A verified traveler stayed at Pleasant Valley Motel West Stockbridge

                          Posted 7 months ago
                          Open Pleasant Valley Motel West Stockbridge hotel guest reviews
                          CheapTickets Verified Review
                          4 out of 5
                          Need a coffee maker in the room. Nice location all needs are close by.

                          A verified traveler from Hopkinton, us stayed at Berkshire Inn

                          Posted 10 months ago
                          Open Berkshire Inn hotel guest reviews
                          CheapTickets Verified Review
                          4 out of 5
                          very nice ad immaculately Clean looks like and old time motel but the room was exceptionally clean and the staff was really friendly

                          A verified traveler from watertown stayed at Wagon Wheel Inn

                          Posted 1 year ago
                          Open Wagon Wheel Inn hotel guest reviews
                          CheapTickets Verified Review
                          5 out of 5
                          Was in town on business and was the only hotel left for the night. Was very clean and staff was very professional

                          A verified traveler stayed at Best Western Plus Berkshire Hills Inn & Suites

                          Posted 1 year ago
                          Open Best Western Plus Berkshire Hills Inn & Suites hotel guest reviews
                          See a list of all hotels in Albany

                          An Airport

                          An Attraction

                          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.