Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


Lenox Vacation Packages

Lenox is well known for its cultural and scenic sights. When you're ready to go, Expedia can make it happen.

Save Time and Money with a Lenox Package Deal

It is very easy to book and save with flight and hotel packages via Expedia. We would like to minimize your worries by combining your hotel and flight bookings to save you some more money. During your trip in Lenox, treat yourself with the extra money.

Earn savings of up to $583 when you book a package deal.

Around 400 partner airlines and 321,000 hotels worldwide are ready for you to secure via our expansive international database.

Check out some of the best deals ever at Expedia and get yourself that special trip you so badly deserve. You won't know why you ever waited so long.

If you have to change your family's travel plans we will honor your cancellation request with no extra fee, on nearly all reservations.

Lenox Vacation Packages

Guests in this area of The Berkshires will be rubbing shoulders with around 2,000 local residents.

You'll find this destination some 110 miles from Boston, the state capital of Massachusetts. It is also roughly 4 miles from Lee.

Bring the whole family to Pleasant Valley Wilderness Sanctuary, a terrific place to spend time with the kids.

Whether you're hanging out with friends or just having a bite to eat in the luscious surroundings, Kennedy Park is a terrific place to kick back and relax.

You'll find loads of fascinating facts and stories within the rooms of the diverse cultural establishments here. Among the best places to visit are The Mount, Ventfort Hall Mansion and Gilded Age Museum and Frelinghuysen Morris House and Studio.

You can immerse yourself in a world of culture and art at B.J. Faulkner Gallery.

The Shakespeare and Company and Tanglewood Music Center are popular performance venues that are visited by travelers and artistically minded locals alike.

Tee off at the Cranwell Golf Club and watch your ball fly down the luscious fairway. This lovely hangout is the perfect place to practice your swing.

If you're looking for something else to do in the Lenox area, visit the Lenox Library.

Accommodation in Lenox

Before you leave, make a reservation for one of the 45 Lenox accommodation options that are listed on Expedia's hotel booking platform.

Discerning travelers with an eye for the timeless traditions of class and style can choose from the Hampton Terrace Inn, at 91 Walker Street, and the Stockbridge Country Inn, at 26 Glendale Road. Should you find that those don't suit your requirements, the Sunset Inn or the Econo Lodge Lee - Great Barrington are two more economical options that may hit the right note for you.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 144 Hotels in Lenox
Yankee Inn $92
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox
     
    3.9
    of 5, from 526 reviews
    2.5 out of 5.0

    Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. Lenox Library and Bousquet Ski Area are also within 3 mi (5 km).

    Hampton Inn & Suites Berkshires Lenox $118
    Hampton Inn & Suites Berkshires Lenox

    Hampton Inn & Suites Berkshires Lenox

    445 Pittsfield Rd, Lenox
       
      4.6
      of 5, from 368 reviews
      2.5 out of 5.0

      Situated in a rural location, this hotel is close to Arrowhead Museum, Bousquet Ski Area, and Kennedy Park. Local attractions also include Pleasant Valley Wilderness Sanctuary and Canoe Meadows Wildlife Sanctuary.

      Courtyard by Marriott Lenox Berkshires $148
      Courtyard by Marriott Lenox Berkshires

      Courtyard by Marriott Lenox Berkshires

      70 Pittsfield Rd, Lenox
         
        4.5
        of 5, from 68 reviews
        3.0 out of 5.0

        Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 3 mi (5 km).

        Cranwell Spa and Golf Resort $159
        Cranwell Spa and Golf Resort

        Cranwell Spa and Golf Resort

        55 Lee Road, Lenox
           
          4.2
          of 5, from 128 reviews
          3.5 out of 5.0

          Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company and Wood's Pond are also within 3 mi (5 km).

          Lenox Inn $42
          Lenox Inn

          Lenox Inn

          525 Pittsfield Rd, Lenox
             
            3.4
            of 5, from 425 reviews
            2.0 out of 5.0

            Situated in Lenox, this hotel is close to Arrowhead Museum, Bousquet Ski Area, and Kennedy Park. Local attractions also include Canoe Meadows Wildlife Sanctuary and Pleasant Valley Wilderness Sanctuary.

            Howard Johnson by Wyndham Lenox $69
            Howard Johnson by Wyndham Lenox

            Howard Johnson by Wyndham Lenox

            462 Pittsfield Rd, Lenox
               
              3.5
              of 5, from 583 reviews
              2.0 out of 5.0

              Situated in Lenox, this motel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary and Canoe Meadows Wildlife Sanctuary are also within 3 mi (5 km).

              Whistler's Inn Bed & Breakfast $115
              Whistler's Inn Bed & Breakfast

              Whistler's Inn Bed & Breakfast

              5 Greenwood Street, Lenox
                 
                4.0
                of 5, from 179 reviews
                3.5 out of 5.0

                Situated in the mountains, this bed & breakfast is close to Lenox Library, Ventfort Hall Mansion and Gilded Age Museum, and Shakespeare and Company. Also nearby are Frelinghuysen Morris House and Studio and Kennedy Park.

                33 Main $329
                33 Main

                33 Main

                33 Main Street, Lenox
                   
                  5.0
                  of 5, from 3 reviews
                  4.0 out of 5.0

                  Located in the heart of Lenox, this bed & breakfast is within a 10-minute walk of Lenox Library and Ventfort Hall Mansion and Gilded Age Museum. Shakespeare and Company and Frelinghuysen Morris House and Studio are also within 1 mi (2 km).

                  Top Deals on Flights

                  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.