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Stockbridge Vacations

Pack those stellar shades. We have Stockbridge vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Stockbridge – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Stockbridge vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Stockbridge

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Stockbridge vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Stockbridge well.

Top Hotel Deals

See all 146 Hotels in Stockbridge
The Red Lion Inn

The Red Lion Inn

30 Main Street, Stockbridge
    3.5 out of 5.0
     
     

    This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival, and Naumkeag. ...

    The Red Lion Inn$140

    The Red Lion Inn$140
    The Inn at Stockbridge

    The Inn at Stockbridge

    30 East Street, Stockbridge
      4.0 out of 5.0
       
       

      Situated in Stockbridge, this bed & breakfast is within 3 mi (5 km) of Berkshire Theatre Festival, Mission House, and Naumkeag. National Shrine of the Divine ...

      The Cottage B&B

      The Cottage B&B

      14 Prospect Hill Road, Stockbridge
        3.0 out of 5.0
         
         

        Situated in Stockbridge, this bed & breakfast is within a 15-minute walk of Naumkeag and National Shrine of the Divine Mercy. Mission House and Mount Greylock ...

        1862 Seasons on Main Bed and Breakfast

        1862 Seasons on Main Bed and Breakfast

        47 Main Street, Stockbridge
          4.5 out of 5.0
           
           

          Situated in Stockbridge, this luxury bed & breakfast is within a 10-minute walk of Mission House and Berkshire Theatre Festival. Naumkeag and National Shrine ...

          Stockbridge Country Inn

          Stockbridge Country Inn

          26 Glendale Road, Stockbridge
            4.5 out of 5.0
             
             

            Situated in Stockbridge, this luxury bed & breakfast is within 1 mi (2 km) of Chesterwood and Norman Rockwell Museum. Berkshire Botanical Garden and Mission ...

            Conroy's B&B

            Conroy's B&B

            11 East Street (Route 7), Stockbridge
              3.5 out of 5.0
               
               

              Situated in the mountains, this bed & breakfast is within 3 mi (5 km) of Berkshire Theatre Festival, Mission House, and Greenock Country Club. Naumkeag and National ...

              Conroy's B&B$170

              Conroy's B&B$170
              Hilton Garden Inn Lenox Pittsfield

              Hilton Garden Inn Lenox Pittsfield

              1032 South Street, Pittsfield
                3.0 out of 5.0
                 
                 

                Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

                Hilton Garden Inn Lenox Pittsfield$127

                Hilton Garden Inn Lenox Pittsfield$127
                Crowne Plaza Pittsfield-Berkshires

                Crowne Plaza Pittsfield-Berkshires

                1 West St, Pittsfield
                  3.5 out of 5.0
                   
                   

                  Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

                  Crowne Plaza Pittsfield-Berkshires$96

                  Crowne Plaza Pittsfield-Berkshires$96
                  Yankee Inn

                  Yankee Inn

                  461 Pittsfield Rd, Lenox
                    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. ...

                    Yankee Inn$92

                    Yankee Inn$92
                    Vacation Village in the Berkshires

                    Vacation Village in the Berkshires

                    276 Brodie Mountain Rd, Hancock
                      3.0 out of 5.0
                       
                       

                      Situated in Hancock, this condo building is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 km) of Waubeeka Golf Links ...

                      Vacation Village in the Berkshires$135

                      Vacation Village in the Berkshires$135

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.