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Pleasantville Vacations

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

Hotwire can help you find your travel bliss with Pleasantville 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 Pleasantville

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 Pleasantville 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 Pleasantville well.

Top Hotel Deals

See all 189 Hotels in Pleasantville
DoubleTree by Hilton Fort Lee - George Washington Bridge

DoubleTree by Hilton Fort Lee - George Washington Bridge

2117 Route 4 Eastbound, Fort Lee
    3.5 out of 5.0
     
     

    This Fort Lee hotel is 0.5 mile from the George Washington Bridge, 6 miles from Garden State Plaza Mall (shopping), 8 miles from the Meadowlands Sports Complex, ...

    DoubleTree by Hilton Fort Lee - George Washington Bridge$132

    DoubleTree by Hilton Fort Lee - George Washington Bridge$132
    Royal Regency Hotel

    Royal Regency Hotel

    165 Tuckahoe Rd, Yonkers
      3.5 out of 5.0
       
       

      Situated in the business district, this hotel is 1.5 mi (2.5 km) from Legoland Discovery Center Westchester and 2.6 mi (4.1 km) from Sarah Lawrence College. ...

      Royal Regency Hotel$131

      Royal Regency Hotel$131
      Tarrytown House Estate on the Hudson

      Tarrytown House Estate on the Hudson

      49 E Sunnyside Lane, Tarrytown
        3.5 out of 5.0
         
         

        Situated in the historical district, this hotel is within 1 mi (2 km) of Lyndhurst Mansion and Irvington Town Hall Theater. Memorial Park and Matthiessen Park ...

        Tarrytown House Estate on the Hudson$134

        Tarrytown House Estate on the Hudson$134
        DoubleTree by Hilton Tarrytown

        DoubleTree by Hilton Tarrytown

        455 S Broadway, Tarrytown
          3.5 out of 5.0
           
           

          Situated in the historical district, this spa hotel is within 2 mi (3 km) of Lyndhurst Mansion, Pierson Park, and Irvington Town Hall Theater. Tarrytown Lighthouse ...

          DoubleTree by Hilton Tarrytown$95

          DoubleTree by Hilton Tarrytown$95
          Hyatt Regency Greenwich

          Hyatt Regency Greenwich

          1800 E Putnam Avenue, Old Greenwich
            4.0 out of 5.0
             
             

            This Hyatt Regency hotel, located on the Stamford/Greenwich border, is minutes from both the heart of downtown Stamford and shopping on Greenwich Avenue. New ...

            Hyatt Regency Greenwich$99

            Hyatt Regency Greenwich$99
            DoubleTree by Hilton Norwalk

            DoubleTree by Hilton Norwalk

            789 Connecticut Ave, Norwalk
              3.5 out of 5.0
               
               

              Situated on the Strip, this hotel is within 3 mi (5 km) of SoNo Switch Tower Museum, Lockwood-Mathews Mansion, and Stepping Stones Museum for Children. Historic ...

              DoubleTree by Hilton Norwalk$95

              DoubleTree by Hilton Norwalk$95
              Hyatt Place New York/Yonkers

              Hyatt Place New York/Yonkers

              7000 Mall Walk, Yonkers
                3.0 out of 5.0
                 
                 

                Located in the heart of Yonkers, this hotel is within 1 mi (2 km) of Empire City Casino and Sarah Lawrence College. Yonkers Raceway and Grace Baptist Church ...

                Hyatt Place New York/Yonkers$149

                Hyatt Place New York/Yonkers$149
                Ramada by Wyndham Rochelle Park Near Paramus

                Ramada by Wyndham Rochelle Park Near Paramus

                375 W Passaic St, Rochelle Park
                  2.0 out of 5.0
                   
                   

                  Situated in Rochelle Park, this hotel is within 1 mi (2 km) of Saddle River County Park and Westfield Garden State Plaza. Orchard Hills Golf Course and Ridgewood ...

                  Ramada by Wyndham Rochelle Park Near Paramus$84

                  Ramada by Wyndham Rochelle Park Near Paramus$84
                  Glen Cove Mansion Hotel

                  Glen Cove Mansion Hotel

                  200 Dosoris Ln, Glen Cove
                    4.0 out of 5.0
                     
                     

                    This historical estate on Long Island's North Shore Gold Coast features a 1910 Georgian mansion surrounded by 55 secluded and landscaped acres, and includes ...

                    Glen Cove Mansion Hotel$149

                    Glen Cove Mansion Hotel$149
                    Overlook Lodge at Bear Mountain

                    Overlook Lodge at Bear Mountain

                    55 Hessian Drive, Bear Mountain
                      2.5 out of 5.0
                       
                       

                      Situated in a state park, this historic hotel is 1.7 mi (2.7 km) from Bear Mountain State Park and within 6 mi (10 km) of Manitoga The Russel Wright Design Center ...

                      Overlook Lodge at Bear Mountain$149

                      Overlook Lodge at Bear Mountain$149

                      Top Flight Deals

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