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Pawling Vacations

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

Hotwire can help you find your travel bliss with Pawling 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 Pawling

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 Pawling 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 Pawling well.

Top Hotel Deals

See all 107 Properties in Pawling
Station Inn Pawling

Station Inn Pawling

7 Memorial Avenue, Pawling
    3.0 out of 5.0
     
     

    Situated in Pawling, this guesthouse is 0.7 mi (1.2 km) from John Kane House and within 12 mi (20 km) of Thunder Ridge Ski Resort and Bull's Bridge. Beekman ...

    The Pawling House Bed & Breakfast

    The Pawling House Bed & Breakfast

    105 West Main Street, Pawling
      3.0 out of 5.0
       
       

      Situated in a rural location, this bed & breakfast is within 20 mi (32 km) of Brewster Public Library, Danbury Music Centre, and Danbury Railway Museum. Kent ...

      The Pawling House Bed & Breakfast$175

      The Pawling House Bed & Breakfast$175
      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$118

        Hampton Inn & Suites Poughkeepsie$118
        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
          Days Inn by Wyndham Poughkeepsie

          Days Inn by Wyndham Poughkeepsie

          536 Haight Ave, Poughkeepsie
            2.0 out of 5.0
             
             

            Situated in Poughkeepsie, this motel is within 1 mi (2 km) of Frances Lehman Loeb Art Center, Vassar College, and Clinton House State Historic Site. Vassar Golf ...

            Days Inn by Wyndham Poughkeepsie$79

            Days Inn by Wyndham Poughkeepsie$79
            Best Western Plus The Inn & Suites At The Falls

            Best Western Plus The Inn & Suites At The Falls

            50 Red Oaks Mill Rd, Poughkeepsie
              2.5 out of 5.0
               
               

              Situated on a river, this hotel is 3 mi (4.8 km) from Frances Lehman Loeb Art Center and 3.1 mi (4.9 km) from Vassar College. Vassar Golf Course and McCann Golf ...

              Best Western Plus The Inn & Suites At The Falls$99

              Best Western Plus The Inn & Suites At The Falls$99
              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
                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
                  Extended Stay America - Fishkill - Route 9

                  Extended Stay America - Fishkill - Route 9

                  25 Merritt Blvd, Fishkill
                    2.5 out of 5.0
                     
                     

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

                    Extended Stay America - Fishkill - Route 9$94

                    Extended Stay America - Fishkill - Route 9$94
                    Residence Inn by Marriott Poughkeepsie

                    Residence Inn by Marriott Poughkeepsie

                    2525 South Rd, Spackenkill
                      3.0 out of 5.0
                       
                       

                      Situated in Poughkeepsie, this aparthotel is within 1 mi (2 km) of Locust Grove and Casperkill Golf Club. McCann Golf Course and Springside National Historic ...

                      Residence Inn by Marriott Poughkeepsie$135

                      Residence Inn by Marriott Poughkeepsie$135

                      Top Flight Deals

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