Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Highland Vacations

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

Hotwire can help you find your travel bliss with Highland 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 Highland

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 Highland 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 Highland well.

Top Hotel Deals

See all 197 Hotels in Highland
Super 8 by Wyndham Highland NY

Super 8 by Wyndham Highland NY

3423 US Highway 9W, Highland
    2.0 out of 5.0
     
     

    Situated in Highland, this hotel is 2.6 mi (4.1 km) from Walkway Over the Hudson State Historic Park and within 6 mi (10 km) of West Park Winery and Apple Greens ...

    Super 8 by Wyndham Highland NY$62

    Super 8 by Wyndham Highland NY$62
    Stonegate Bed and Breakfast

    Stonegate Bed and Breakfast

    34 North Road, Highland
      3.5 out of 5.0
       
       

      Situated in a rural location, this bed & breakfast is within 3 mi (5 km) of Walkway Over the Hudson State Historic Park, Poughkeepsie Bridge, and Mid-Hudson ...

      Americas Best Value Inn-Highland/Poughkeepsie

      Americas Best Value Inn-Highland/Poughkeepsie

      3497 Us Highway 9w, Highland
        2.0 out of 5.0
         
         

        Situated in Highland, this motel is within 3 mi (5 km) of Walkway Over the Hudson State Historic Park, Poughkeepsie Bridge, and Mid-Hudson Bridge. Bardavon 1869 ...

        Americas Best Value Inn-Highland/Poughkeepsie$63

        Americas Best Value Inn-Highland/Poughkeepsie$63
        Atlas Motor Lodge

        Atlas Motor Lodge

        125 Tillson Avenue EXT, Highland
          2.0 out of 5.0
           
           

          Situated in Highland, this motel is within 2 mi (3 km) of Walkway Over the Hudson State Historic Park, Poughkeepsie Bridge, and Mid-Hudson Bridge. Mid-Hudson ...

          Atlas Motor Lodge$70

          Atlas Motor Lodge$70
          Americas Best Value Inn-New Paltz

          Americas Best Value Inn-New Paltz

          7 Terwilliger Ln, New Paltz
            2.0 out of 5.0
             
             

            Situated in New Paltz, this motel is within 2 mi (3 km) of State University of New York-New Paltz, G. Steve Jordan Gallery, and Loren Campbell Memorial Field. ...

            Americas Best Value Inn-New Paltz$85

            Americas Best Value Inn-New Paltz$85
            Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport

            Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport

            915 Union Ave, New Windsor
              2.0 out of 5.0
               
               

              Situated in New Windsor, this hotel is within 3 mi (5 km) of Orange County Choppers, National Purple Heart Hall of Honor, and New Windsor Cantonment State Historic ...

              Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport$84

              Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport$84
              Hampton Inn & Suites Poughkeepsie

              Hampton Inn & Suites Poughkeepsie

              2361 South Rd, Crown Heights
                2.5 out of 5.0
                 
                 

                Situated in the historical district, this hotel is 0.2 mi (0.3 km) from Casperkill Golf Club and within 3 mi (5 km) of Locust Grove and McCann Golf Course. Poughkeepsie ...

                Hampton Inn & Suites Poughkeepsie$114

                Hampton Inn & Suites Poughkeepsie$114
                Super 8 by Wyndham Kingston

                Super 8 by Wyndham Kingston

                487 Washington Ave, Kingston
                  2.0 out of 5.0
                   
                   

                  Situated in Kingston, this motel is within a 15-minute walk of Senate House State Historic Site, Forsyth Park, and Volunteer Fireman's Hall and Museum of Kingston. ...

                  Super 8 by Wyndham Kingston$72

                  Super 8 by Wyndham Kingston$72
                  Ramada by Wyndham Fishkill

                  Ramada by Wyndham Fishkill

                  542 Route 9, Fishkill
                    3.0 out of 5.0
                     
                     

                    Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum, Fishkill Golf Course, and Blodgett Memorial Library. SplashDown Beach is ...

                    Ramada by Wyndham Fishkill$99

                    Ramada by Wyndham Fishkill$99
                    Magnuson Hotel Fishkill

                    Magnuson Hotel Fishkill

                    20 Schuyler Blvd, Fishkill
                      2.5 out of 5.0
                       
                       

                      Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum, Blodgett Memorial Library, and Fishkill Golf Course. SplashDown Beach is ...

                      Magnuson Hotel Fishkill$95

                      Magnuson Hotel Fishkill$95

                      Top Flight Deals

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