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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 146 Properties in Middlebury
Courtyard Middlebury

Courtyard Middlebury

309 Court Street, Middlebury
    3.0 out of 5.0
     
     

    This family-friendly Middlebury hotel is located in a rural location, within 1 mi (2 km) of Town Hall Theater, Vermont Folklife Center, and Henry Sheldon Museum ...

    Courtyard Middlebury$130

    Courtyard Middlebury$130
    Middlebury Inn

    Middlebury Inn

    14 Court Square, Middlebury
      3.0 out of 5.0
       
       

      Located in the heart of Middlebury, this spa hotel is within a 15-minute walk of Town Hall Theater and Middlebury College. National Museum of the Morgan Horse ...

      Middlebury Inn$119

      Middlebury Inn$119
      Swift House Inn

      Swift House Inn

      25 Stewart Ln, Middlebury
        3.0 out of 5.0
         
         

        Located in the heart of Middlebury, this golf hotel is within 1 mi (2 km) of National Museum of the Morgan Horse and Middlebury College. Town Hall Theater and ...

        Swift House Inn$144

        Swift House Inn$144
        The Inn on the Green

        The Inn on the Green

        71 South Pleasant St., Middlebury
          3.5 out of 5.0
           
           

          Located in the heart of Middlebury, this guesthouse is within a 15-minute walk of Town Hall Theater and Middlebury College. National Museum of the Morgan Horse ...

          The Inn on the Green$149

          The Inn on the Green$149
          Middlebury Sweets Motel

          Middlebury Sweets Motel

          1395 Rt 7 South, Middlebury
            2.5 out of 5.0
             
             

            Situated in Middlebury, this motel is 2.2 mi (3.5 km) from Town Hall Theater and 2.6 mi (4.1 km) from Middlebury College. Vermont Folklife Center and Henry Sheldon ...

            Middlebury Sweets Motel$126

            Middlebury Sweets Motel$126
            Blue Spruce Motel

            Blue Spruce Motel

            2428 Route 7 South, Middlebury
              2.0 out of 5.0
               
               

              Situated in Middlebury, this motel is within 6 mi (10 km) of Vermont Folklife Center, Middlebury College, and Henry Sheldon Museum of Vermont History. National ...

              Bryn Meadow Farm and B&B

              Bryn Meadow Farm and B&B

              3960 Spear Street, Charlotte
                3.0 out of 5.0
                 
                 

                Situated in Charlotte, this bed & breakfast is within 9 mi (15 km) of Shelburne Museum, Vermont Teddy Bears, and Shelburne Vineyard. Lake Champlain and Shelburne ...

                Bryn Meadow Farm and B&B$125

                Bryn Meadow Farm and B&B$125
                Lake Bomoseen Lodge

                Lake Bomoseen Lodge

                2551 Vermont 30N, Bomoseen
                  3.5 out of 5.0
                   
                   

                  Located in Bomoseen, this beachfront lodge is next to a golf course, 0.1 mi (0.1 km) from Prospect Bay Country Club, and within 9 mi (15 km) of Halfmoon Pond ...

                  Lake Bomoseen Lodge$165

                  Lake Bomoseen Lodge$165
                  Basin Harbor

                  Basin Harbor

                  4800 Basin Harbor Rd, Vergennes
                    3.5 out of 5.0
                     
                     

                    Nestled on the beach, this Vergennes hotel is within a 5-minute walk of Lake Champlain Maritime Museum and Lake Champlain. Button Bay State Park is 1.3 mi (2.1 ...

                    Basin Harbor$197

                    Basin Harbor$197
                    Super 8 by Wyndham Ticonderoga

                    Super 8 by Wyndham Ticonderoga

                    1144 Wicker St, Ticonderoga
                      2.0 out of 5.0
                       
                       

                      Situated on a lake, this motel is within 2 mi (3 km) of Ticonderoga Historical Society, Ticonderoga Cartoon Museum, and Ticonderoga Heritage Museum. Ticondroga ...

                      Super 8 by Wyndham Ticonderoga$89

                      Super 8 by Wyndham Ticonderoga$89

                      Top Flight Deals

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