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Middlebury Vacations

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

Hotwire can help you find your travel bliss with Middlebury 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 Middlebury

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 Middlebury 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 Middlebury well.

Top Hotel Deals

See all 64 Hotels in Middlebury
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

105 Crystal Heights Blvd, Middlebury
    2.5 out of 5.0
     
     

    Located in the heart of Middlebury, this hotel is within 9 mi (15 km) of Menno-Hof Museum of Culture, Shipshewana Auction and Flea Market, and North Park. Elkhart ...

    Hampton Inn & Suites Middlebury$93

    Hampton Inn & Suites Middlebury$93
    That Pretty Place Bed & Breakfast

    That Pretty Place Bed & Breakfast

    212 U.S. 20, Middlebury
      3.0 out of 5.0
       
       

      Situated in Middlebury, this golf bed & breakfast is within 9 mi (15 km) of Menno-Hof Museum of Culture, Shipshewana Auction and Flea Market, and North Park. ...

      The Wellington Cottage

      The Wellington Cottage

      7420 N 1160 W, Middlebury
        3.0 out of 5.0
         
         

        Situated in Middlebury, this cottage is in the same area as North Park. Regional attractions also include Shipshewana Auction and Flea Market and Menno-Hof Museum ...

        Van Buren Hotel

        Van Buren Hotel

        1175 Van Buren Street, Shipshewana
          2.5 out of 5.0
           
           

          Situated in Shipshewana, this hotel is within 1 mi (2 km) of North Park and Shipshewana Auction and Flea Market. Menno-Hof Museum of Culture is 1.4 mi (2.3 km) ...

          Van Buren Hotel$105

          Van Buren Hotel$105
          Microtel Inn & Suites by Wyndham Elkhart

          Microtel Inn & Suites by Wyndham Elkhart

          3301 Plaza Ct, Elkhart
            2.0 out of 5.0
             
             

            Situated in Elkhart, this hotel is 3.1 mi (4.9 km) from Wellfield Botanic Gardens and within 6 mi (10 km) of Ruthmere Mansion and NIBCO Water and Ice Park. The ...

            Microtel Inn & Suites by Wyndham Elkhart$72

            Microtel Inn & Suites by Wyndham Elkhart$72
            Farmstead Inn & Conference Center

            Farmstead Inn & Conference Center

            370 S Van Buren St, Shipshewana
              2.5 out of 5.0
               
               

              Situated in Shipshewana, this hotel is steps from Shipshewana Auction and Flea Market and Menno-Hof Museum of Culture. North Park is 0.7 mi (1.1 km) away.

              Blue Gate Garden Inn

              Blue Gate Garden Inn

              800 South Van Buren Street, Shipshewana
                2.5 out of 5.0
                 
                 

                Situated in a shopping district, this hotel is within a 10-minute walk of Menno-Hof Museum of Culture and Shipshewana Auction and Flea Market. North Park is ...

                Super 8 by Wyndham Shipshewana

                Super 8 by Wyndham Shipshewana

                740 S Van Buren St, Shipshewana
                  2.0 out of 5.0
                   
                   

                  Situated in Shipshewana, this hotel is within a 10-minute walk of Menno-Hof Museum of Culture and Shipshewana Auction and Flea Market. North Park is 1 mi (1.6 ...

                  Super 8 by Wyndham Shipshewana$72

                  Super 8 by Wyndham Shipshewana$72
                  Best Western Inn & Suites

                  Best Western Inn & Suites

                  3326 Cassopolis Street, Elkhart
                    2.5 out of 5.0
                     
                     

                    Situated in Elkhart, this hotel is 2.7 mi (4.4 km) from Wellfield Botanic Gardens and 2.8 mi (4.6 km) from Ruthmere Mansion. NIBCO Water and Ice Park and The ...

                    Best Western Inn & Suites$89

                    Best Western Inn & Suites$89
                    Comfort Suites South

                    Comfort Suites South

                    27838 County Road 24, Elkhart
                      2.5 out of 5.0
                       
                       

                      Situated in Elkhart, this hotel is 0.7 mi (1.1 km) from Hall of Heroes Super Hero Museum and within 6 mi (10 km) of The Lerner and National New York Central ...

                      Comfort Suites South$95

                      Comfort Suites South$95

                      Top Flight Deals

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