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Round Top Vacations

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

Hotwire can help you find your travel bliss with Round Top 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 Round Top

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 Round Top 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 Round Top well.

Top Hotel Deals

See all 202 Hotels in Round Top
Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus

430 Winter Clove Road, Round Top
    2.5 out of 5.0
     
     

    Situated in Round Top, this hotel is 5.7 mi (9.2 km) from Bailiwick Ranch and Discovery Zoo and 9.7 mi (15.6 km) from Thunderhart Golf Course. Thomas Cole National ...

    Riedlbauer's Resort

    Riedlbauer's Resort

    57 Ravine Dr., Round Top
      2.5 out of 5.0
       
       

      Situated in the mountains, this hotel is 5.3 mi (8.5 km) from Bailiwick Ranch and Discovery Zoo and 9.3 mi (15 km) from Thunderhart Golf Course. Thomas Cole ...

      Blackhead Mountain Lodge & Country Club

      Blackhead Mountain Lodge & Country Club

      50 Crows Nest Road, Round Top
        3.0 out of 5.0
         
         

        Situated in Round Top, this golf hotel is 6.8 mi (11 km) from Bailiwick Ranch and Discovery Zoo and 9.3 mi (15 km) from Thunderhart Golf Course. Thomas Cole ...

        The George Ellen Bed and Breakfast

        The George Ellen Bed and Breakfast

        248 Pollys Rock Rd, Round Top
          3.5 out of 5.0
           
           

          Situated in Round Top, this bed & breakfast is 3.7 mi (5.9 km) from Bailiwick Ranch and Discovery Zoo and 9.9 mi (16 km) from Thunderhart Golf Course. Thomas ...

          Hampton Inn Kingston

          Hampton Inn Kingston

          1307 Ulster Ave, Kingston
            2.5 out of 5.0
             
             

            Situated in Kingston, this hotel is 0.4 mi (0.6 km) from Hudson Valley Mall and 2.9 mi (4.7 km) from Ulster Performing Arts Center. Old Dutch Church and Senate ...

            Hampton Inn Kingston$125

            Hampton Inn Kingston$125
            Holiday Inn Express & Suites Kingston-Ulster

            Holiday Inn Express & Suites Kingston-Ulster

            1835 Ulster Avenue, Lake Katrine
              2.5 out of 5.0
               
               

              Situated in the historical district, this hotel is 1.5 mi (2.4 km) from Hudson Valley Mall and within 6 mi (10 km) of Ulster Performing Arts Center and Poet's ...

              Holiday Inn Express & Suites Kingston-Ulster$117

              Holiday Inn Express & Suites Kingston-Ulster$117
              Residence Inn by Marriott Kingston

              Residence Inn by Marriott Kingston

              800 Frank Sottile Boulevard, Kingston
                3.0 out of 5.0
                 
                 

                Situated in Kingston, this hotel is 0.3 mi (0.5 km) from Hudson Valley Mall and within 6 mi (10 km) of Ulster Performing Arts Center and Old Dutch Church. Senate ...

                Residence Inn by Marriott Kingston$129

                Residence Inn by Marriott Kingston$129
                The Barlow Hotel

                The Barlow Hotel

                542 Warren Street, Hudson
                  3.0 out of 5.0
                   
                   

                  Situated in the city center, this hotel is close to Hudson Area Library, Hudson Opera House, and FASNY Museum of Firefighting. Local attractions also include ...

                  The Barlow Hotel$150

                  The Barlow Hotel$150
                  Morning Glory B&B Woodstock NY

                  Morning Glory B&B Woodstock NY

                  141 Tinker Street, Woodstock
                    3.0 out of 5.0
                     
                     

                    Situated in a state park, this bed & breakfast is 0.3 mi (0.5 km) from Woodstock Public Library and 3.1 mi (5 km) from Overlook Mountain Trailhead. Karma Triyana ...

                    Winwood Inn & Condominiums

                    Winwood Inn & Condominiums

                    5220 NY-23, Windham
                      3.0 out of 5.0
                       
                       

                      Conveniently located near the ski slopes, this Windham resort is in the mountains, within 2 mi (3 km) of Windham Country Club and Windham Mountain Resort, and ...

                      Top Flight Deals

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