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Middleburg Vacations

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

Hotwire can help you find your travel bliss with Middleburg 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 Middleburg

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 Middleburg 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 Middleburg well.

Top Hotel Deals

See all 140 Properties in Middleburg
Omni Jacksonville Hotel

Omni Jacksonville Hotel

245 Water St, Jacksonville
    4.0 out of 5.0
     
     

    The Omni Jacksonville Hotel is downtown, in the cultural and business districts. The hotel is opposite the Times-Union Center for the Performing Arts, one block ...

    Omni Jacksonville Hotel$79

    Omni Jacksonville Hotel$79
    Hyatt Regency Jacksonville

    Hyatt Regency Jacksonville

    225 E Coastline Dr, Jacksonville
      4.0 out of 5.0
       
       

      This downtown riverfront hotel is in the city's business and retail district next to Jacksonville shopping, dining, and entertainment venues.

      Hyatt Regency Jacksonville$119

      Hyatt Regency Jacksonville$119
      Best Western Southside Hotel & Suites

      Best Western Southside Hotel & Suites

      4580 Collins Rd, Orange Park
        2.5 out of 5.0
         
         

        Situated in the business district, this hotel is 1.2 mi (1.9 km) from bestbet Orange Park and 2.4 mi (3.8 km) from Jacksonville Naval Air Station. Westside Regional ...

        Best Western Southside Hotel & Suites$67

        Best Western Southside Hotel & Suites$67
        Lexington Hotel & Conference Center - Jacksonville Riverwalk

        Lexington Hotel & Conference Center - Jacksonville Riverwalk

        1515 Prudential Dr, Jacksonville
          3.5 out of 5.0
           
           

          The Lexington Hotel & Conference Center – Jacksonville Riverwalk is located across from Jacksonville Landing, on the south bank of the river, 1 mile (1.6 kilometers) ...

          Lexington Hotel & Conference Center - Jacksonville Riverwalk$95

          Lexington Hotel & Conference Center - Jacksonville Riverwalk$95
          Baymont by Wyndham Jacksonville/Butler Blvd

          Baymont by Wyndham Jacksonville/Butler Blvd

          7030 Bonneval Road, Jacksonville
            2.5 out of 5.0
             
             

            Located in Southpoint, this hotel is within 6 mi (10 km) of Dog Wood Park of Jacksonville, St. Johns Town Center, and The Avenues. Crabtree Park and Hands on ...

            Baymont by Wyndham Jacksonville/Butler Blvd$72

            Baymont by Wyndham Jacksonville/Butler Blvd$72
            Country Inn & Suites by Radisson, Jacksonville, FL

            Country Inn & Suites by Radisson, Jacksonville, FL

            5945 Youngerman Cir E, Jacksonville
              3.0 out of 5.0
               
               

              Situated in Jacksonville, this hotel is 1.3 mi (2 km) from Orange Park Mall and 2.8 mi (4.6 km) from Orange Park Medical Center. Jacksonville Naval Air Station ...

              Country Inn & Suites by Radisson, Jacksonville, FL$87

              Country Inn & Suites by Radisson, Jacksonville, FL$87
              Stars Rest Inn

              Stars Rest Inn

              510 Lane Avenue S, Jacksonville
                2.0 out of 5.0
                 
                 

                Situated in Jacksonville, this motel is 2.8 mi (4.5 km) from Hyde Park Golf Club and within 6 mi (10 km) of Cummer Museum of Art and Gardens and Jacksonville ...

                Stars Rest Inn$43

                Stars Rest Inn$43
                Motel 6 Jacksonville - Orange Park

                Motel 6 Jacksonville - Orange Park

                6107 Youngerman Circle, Jacksonville
                  2.0 out of 5.0
                   
                   

                  Situated in Jacksonville, this motel is 1.4 mi (2.2 km) from Orange Park Mall and 3 mi (4.8 km) from Orange Park Medical Center. Jacksonville Naval Air Station ...

                  Motel 6 Jacksonville - Orange Park$48

                  Motel 6 Jacksonville - Orange Park$48
                  Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows

                  Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows

                  9150 Baymeadows Road, Jacksonville
                    3.0 out of 5.0
                     
                     

                    Situated in Jacksonville, this hotel is within 6 mi (10 km) of Dog Wood Park of Jacksonville, The Avenues, and Crabtree Park. St. Johns Town Center and Museum ...

                    Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows$79

                    Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows$79
                    Extended Stay America - Jacksonville - Deerwood Park

                    Extended Stay America - Jacksonville - Deerwood Park

                    8801 Perimeter Park Blvd, Jacksonville
                      2.5 out of 5.0
                       
                       

                      Located in Southpoint-Butler Blvd, this hotel is 2.5 mi (4 km) from St. Johns Town Center and 2.9 mi (4.7 km) from Hands on Children's Museum. University of ...

                      Extended Stay America - Jacksonville - Deerwood Park$67

                      Extended Stay America - Jacksonville - Deerwood Park$67

                      Top Flight Deals

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