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Historic Main Street Vacations

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

Hotwire can help you find your travel bliss with Historic Main Street 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 Historic Main Street

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 Historic Main Street 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 Historic Main Street well.

Top Hotel Deals

See all 41 Hotels in Historic Main Street
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

75 Railroad St, Keene
    3.0 out of 5.0
     
     

    Situated in Historic Main Street, this hotel is within a 5-minute walk of Colonial Theatre and Central Square. Horatio Colony Museum and Historical Society of ...

    Courtyard by Marriott Keene Downtown$107

    Courtyard by Marriott Keene Downtown$107
    Fairfield Inn & Suites by Marriott Keene Downtown

    Fairfield Inn & Suites by Marriott Keene Downtown

    30 Main Street, Keene
      3.0 out of 5.0
       
       

      Located in the heart of Historic Main Street, this hotel is steps from Central Square and Colonial Theatre. Horatio Colony Museum and Historical Society of Cheshire ...

      Fairfield Inn & Suites by Marriott Keene Downtown$107

      Fairfield Inn & Suites by Marriott Keene Downtown$107
      Best Western Plus Keene Hotel

      Best Western Plus Keene Hotel

      401 Winchester St, Keene
        3.0 out of 5.0
         
         

        This family-friendly Keene hotel is located in the suburbs, within 1 mi (2 km) of Thorne-Sagendorph Art Gallery, Cheshire Children's Museum, and Historical Society ...

        Best Western Plus Keene Hotel$89

        Best Western Plus Keene Hotel$89
        Colonial Motel And Spa

        Colonial Motel And Spa

        889 Putney Rd, Brattleboro
          3.0 out of 5.0
           
           

          Located in the heart of Brattleboro, this motel is 0.7 mi (1.1 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro ...

          Colonial Motel And Spa$69

          Colonial Motel And Spa$69
          Hampton Inn Brattleboro

          Hampton Inn Brattleboro

          1378 Putney Road, Brattleboro
            2.5 out of 5.0
             
             

            Situated in Brattleboro, this hotel is 0.7 mi (1.2 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

            Hampton Inn Brattleboro$107

            Hampton Inn Brattleboro$107
            Motel 6 Brattleboro

            Motel 6 Brattleboro

            1254 Putney Rd, Brattleboro
              2.0 out of 5.0
               
               

              Situated in Brattleboro, this motel is 0.5 mi (0.8 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

              Motel 6 Brattleboro$54

              Motel 6 Brattleboro$54
              Days Inn by Wyndham Keene NH

              Days Inn by Wyndham Keene NH

              3 Ash Brook Road, Keene
                2.0 out of 5.0
                 
                 

                Situated in Keene, this hotel is within 2 mi (3 km) of Cheshire Children's Museum, Thorne-Sagendorph Art Gallery, and Alumni Field. Horatio Colony Museum and ...

                Days Inn by Wyndham Keene NH$80

                Days Inn by Wyndham Keene NH$80
                Quality Inn & Conference Center

                Quality Inn & Conference Center

                1380 Putney Road, Brattleboro
                  2.5 out of 5.0
                   
                   

                  Situated in Brattleboro, this hotel is 0.8 mi (1.3 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

                  Quality Inn & Conference Center$65

                  Quality Inn & Conference Center$65
                  Holiday Inn Express Hotel & Suites Brattleboro

                  Holiday Inn Express Hotel & Suites Brattleboro

                  100 Chickering Drive, Brattleboro
                    2.5 out of 5.0
                     
                     

                    Situated in a rural location, this hotel is 1 mi (1.6 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro ...

                    Holiday Inn Express Hotel & Suites Brattleboro$111

                    Holiday Inn Express Hotel & Suites Brattleboro$111
                    Super 8 by Wyndham Brattleboro

                    Super 8 by Wyndham Brattleboro

                    1043 Putney Road, Brattleboro
                      2.0 out of 5.0
                       
                       

                      Situated in Brattleboro, this motel is 0.4 mi (0.7 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

                      Super 8 by Wyndham Brattleboro$67

                      Super 8 by Wyndham Brattleboro$67

                      Top Flight Deals

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