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Roxbury Vacations

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

Hotwire can help you find your travel bliss with Roxbury 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 Roxbury

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 Roxbury 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 Roxbury well.

Top Hotel Deals

See all 123 Hotels in Roxbury
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 ...

    Buena Vista Inn

    Buena Vista Inn

    18718 NY-28, Delhi
      2.5 out of 5.0
       
       

      Situated in Delhi, this motel is in the same region as Hanford Mills Museum.

      Black Bear Lodge

      Black Bear Lodge

      11985 RT23A, Prattsville
        2.5 out of 5.0
         
         

        Situated in Prattsville, this motel is 10.9 mi (17.6 km) from Hunter Mountain and 11.8 mi (19 km) from Windham Mountain Resort. Windham Vineyards and Winery ...

        The Queen of the Catskills B&B

        The Queen of the Catskills B&B

        157 W Main St, Stamford
          3.0 out of 5.0
           
           

          Situated in Stamford, this bed & breakfast is 1.6 mi (2.6 km) from Stamford Golf Club and within 25 mi (40 km) of Hanford Mills Museum and Windham Vineyards ...

          The Wheelhouse Inn

          The Wheelhouse Inn

          282 Main st, Pine Hill
             
             

            Situated in a state park, this hotel is close to Belleayre Beach at Pine Hill Lake and Belleayre Mountain. Regional attractions also include Delaware & Ulster ...

            Meadowood Inn

            Meadowood Inn

            50 Hornbeck St , Margaretville
              3.0 out of 5.0
               
               

              Situated in Arkville, this bed & breakfast is close to Union Grove Distillery and Delaware & Ulster Railroad. Area attractions also include Canada Falls and ...

              Antique Rose Inn Windham

              Antique Rose Inn Windham

              326 State Route 296, Windham
                3.0 out of 5.0
                 
                 

                Situated in Windham, this bed & breakfast is 1.1 mi (1.8 km) from Windham Country Club and 2.4 mi (3.9 km) from Windham Mountain Resort. Mountain Top Arboretum ...

                Hotel Vienna

                Hotel Vienna

                107 State Route 296, Windham
                  2.5 out of 5.0
                   
                   

                  Situated in Windham, this hotel is 0.5 mi (0.8 km) from Windham Country Club and 1.8 mi (3 km) from Windham Mountain Resort. Windham Vineyards and Winery and ...

                  Hotel Vienna$129

                  Hotel Vienna$129
                  Margaretville Motel

                  Margaretville Motel

                  42480 State Highway Rte. 28, Margaretville
                    2.5 out of 5.0
                     
                     

                    Situated in Margaretville, this motel is 5.7 mi (9.2 km) from Canada Falls and 9.2 mi (14.9 km) from Belleayre Mountain. Plattekill Mountain and Giant Ledge ...

                    Captain's Inn Point Lookout

                    Captain's Inn Point Lookout

                    7604 State Route 23, East Windham
                      3.0 out of 5.0
                       
                       

                      Situated in East Windham, this hotel is within 9 mi (15 km) of Windham Country Club, Zoom Flume, and Windham Mountain Resort. Windham Vineyards and Winery is ...

                      Top Flight Deals

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