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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 126 Properties in Middlebury
Tucker Hill Inn

Tucker Hill Inn

96 Tucker Hill Rd., Middlebury
    2.5 out of 5.0
     
     

    Situated in the suburbs, this bed & breakfast is 2.6 mi (4.2 km) from Hop Brook Lake and 2.7 mi (4.3 km) from Quassy Amusement Park. Harrub Pilgrim Memorial ...

    Tucker Hill Inn$145

    Tucker Hill Inn$145
    Omni New Haven Hotel at Yale

    Omni New Haven Hotel at Yale

    155 Temple St, New Haven
      4.0 out of 5.0
       
       

      Combining classic New England style with up-to-date features, this 19-story hotel is one block from the historic New Haven Green and the Shubert Theater and ...

      Omni New Haven Hotel at Yale$167

      Omni New Haven Hotel at Yale$167
      La Quinta Inn & Suites New Haven

      La Quinta Inn & Suites New Haven

      400 Sargent Dr, New Haven
         
         

        Located in Long Wharf, this hotel is 0.1 mi (0.1 km) from Long Wharf Theatre and 1.7 mi (2.7 km) from Yale University. Knights of Columbus Museum and Wooster ...

        La Quinta Inn & Suites New Haven$84

        La Quinta Inn & Suites New Haven$84
        New Haven Village Suites

        New Haven Village Suites

        3 Long Wharf Dr, New Haven
          3.0 out of 5.0
           
           

          This all-suite hotel is near all downtown New Haven attractions, 1 mile from Yale University, and within 5 miles of Tweed/New Haven Airport. Albertus Magnus ...

          New Haven Village Suites$122

          New Haven Village Suites$122
          Hyatt Place Milford / New Haven

          Hyatt Place Milford / New Haven

          190 Old Gate Lane, Milford
            3.0 out of 5.0
             
             

            Just off highway I-95, Hyatt Place Milford / New Haven is a 5-minute drive from Westfield Connecticut Post shopping mall. Trains from nearby Milford Station ...

            Hyatt Place Milford / New Haven$104

            Hyatt Place Milford / New Haven$104
            Hawthorn Suites by Wyndham Hartford Meriden

            Hawthorn Suites by Wyndham Hartford Meriden

            1151 E Main St, Meriden
              3.0 out of 5.0
               
               

              Situated in the business district, this hotel is within 1 mi (2 km) of Saint Johns Field, Black Pond State Wildlife Area, and Connecticut Law Enforcement Memorial. ...

              Hawthorn Suites by Wyndham Hartford Meriden$81

              Hawthorn Suites by Wyndham Hartford Meriden$81
              La Quinta Inn & Suites Danbury

              La Quinta Inn & Suites Danbury

              116 Newtown Road, Danbury
                2.5 out of 5.0
                 
                 

                Situated in Danbury, this hotel is 1 mi (1.6 km) from Still River Greenway and within 3 mi (5 km) of Danbury Railway Museum and Danbury Music Centre. Danbury ...

                La Quinta Inn & Suites Danbury$95

                La Quinta Inn & Suites Danbury$95
                Best Western Plus North Haven Hotel

                Best Western Plus North Haven Hotel

                201 Washington Avenue, North Haven
                  3.0 out of 5.0
                   
                   

                  Situated in North Haven, this hotel is 1.8 mi (2.9 km) from Wharton Brook State Park and within 6 mi (10 km) of Tradition Golf Club at Wallingford and Toyota ...

                  Best Western Plus North Haven Hotel$98

                  Best Western Plus North Haven Hotel$98
                  Comfort Inn & Suites

                  Comfort Inn & Suites

                  900 East Main Street, Meriden
                    2.5 out of 5.0
                     
                     

                    Located in the heart of Meriden, this hotel is within 2 mi (3 km) of Saint Johns Field, Black Pond State Wildlife Area, and Connecticut Law Enforcement Memorial. ...

                    Comfort Inn & Suites$71

                    Comfort Inn & Suites$71
                    New Haven Inn

                    New Haven Inn

                    100 Pond Lily Ave, New Haven
                      1.5 out of 5.0
                       
                       

                      Situated in New Haven, this motel is 2 mi (3.3 km) from Southern Connecticut State University and 2.4 mi (3.9 km) from Yale Bowl. Yale Golf Course and Connecticut ...

                      New Haven Inn$51

                      New Haven Inn$51

                      Top Flight Deals

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