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Chatham Vacations

Pack those stellar shades. We have Chatham 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 Chatham – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Chatham 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 Chatham

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 Chatham 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 Chatham well.

Top Hotel Deals

See all 180 Hotels in Chatham
Chatham Travel Lodge

Chatham Travel Lodge

598 NY-295, Chatham
    2.5 out of 5.0
     
     

    Situated in Chatham, this motel is within 9 mi (15 km) of The Mac-Haydn Theatre, Shaker Museum and Library, and Valatie Free Library. Van Alen House and Furnace ...

    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$110

      Hilton Garden Inn Lenox Pittsfield$110
      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
        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$111

          The Red Lion Inn$111
          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
            Comfort Inn Glenmont - Albany South

            Comfort Inn Glenmont - Albany South

            37 Route 9W, Glenmont
              2.5 out of 5.0
               
               

              Located in the heart of Glenmont, this hotel is within 3 mi (5 km) of Historic Cherry Hill, New York State Museum, and The Egg. Times Union Center and Washington ...

              Comfort Inn Glenmont - Albany South$108

              Comfort Inn Glenmont - Albany South$108
              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$105

                Vacation Village in the Berkshires$105
                Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

                Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

                249 Stockbridge Rd, Great Barrington
                  2.5 out of 5.0
                   
                   

                  This family-friendly Great Barrington hotel is located in the mountains, within 2 mi (3 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. Ski Butternut ...

                  Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$127

                  Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires$127
                  Americas Best Value Inn-Albany / East Greenbush

                  Americas Best Value Inn-Albany / East Greenbush

                  576 Columbia Turnpike, East Greenbush
                    2.0 out of 5.0
                     
                     

                    Situated in East Greenbush, this motel is within 6 mi (10 km) of Crailo State Historic Site, New York State Museum, and The Egg. Times Union Center and New York ...

                    Americas Best Value Inn-Albany / East Greenbush$58

                    Americas Best Value Inn-Albany / East Greenbush$58
                    Courtyard by Marriott Lenox Berkshires

                    Courtyard by Marriott Lenox Berkshires

                    70 Pittsfield Rd, Lenox
                      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 ...

                      Courtyard by Marriott Lenox Berkshires$134

                      Courtyard by Marriott Lenox Berkshires$134

                      Top Flight Deals

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