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Windham Vacations

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

Hotwire can help you find your travel bliss with Windham 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 Windham

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 Windham 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 Windham well.

Top Hotel Deals

See all 178 Properties in Windham
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 ...

    Antique Rose Inn Windham$105

    Antique Rose Inn Windham$105
    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
      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 ...

        Winwood Inn & Condominiums$147

        Winwood Inn & Condominiums$147
        Cave Mountain Motel

        Cave Mountain Motel

        10978 STATE RTE 23, Windham
          2.5 out of 5.0
           
           

          Situated in Windham, this motel is 1.8 mi (2.9 km) from Windham Mountain Resort and 2.9 mi (4.7 km) from Windham Country Club. Windham Vineyards and Winery and ...

          Cave Mountain Motel$89

          Cave Mountain Motel$89
          The Thompson House

          The Thompson House

          19 Rt. 296, Windham
            2.5 out of 5.0
             
             

            This family-friendly Windham hotel is located in a state park, within 2 mi (3 km) of Windham Country Club and Windham Mountain Resort. Windham Vineyards and ...

            Georgian Garden Inn

            Georgian Garden Inn

            5159 state route 23, Windham
              3.0 out of 5.0
               
               

              Nestled on the beach, this Windham bed & breakfast is 0.7 mi (1.2 km) from Windham Country Club and 1.5 mi (2.4 km) from Windham Mountain Resort. Windham Vineyards ...

              Georgian Garden Inn$169

              Georgian Garden Inn$169
              Copper Kettle Cottages

              Copper Kettle Cottages

              5098 Main Street, Windham
                2.5 out of 5.0
                 
                 

                Situated in Windham, this motel is 0.5 mi (0.8 km) from Windham Country Club and 1.8 mi (2.9 km) from Windham Mountain Resort. Windham Vineyards and Winery and ...

                Copper Kettle Cottages$75

                Copper Kettle Cottages$75
                Albergo Allegria Bed and Breakfast Hotel

                Albergo Allegria Bed and Breakfast Hotel

                43 State Route 296, Windham
                  3.5 out of 5.0
                   
                   

                  Situated in the historical district, this bed & breakfast is 0.3 mi (0.4 km) from Windham Country Club and 1.6 mi (2.6 km) from Windham Mountain Resort. Windham ...

                  Albergo Allegria Bed and Breakfast Hotel$114

                  Albergo Allegria Bed and Breakfast Hotel$114
                  Beds on Clouds

                  Beds on Clouds

                  5320 Main Street, Windham
                    3.0 out of 5.0
                     
                     

                    Situated in Windham, this spa bed & breakfast is 0.8 mi (1.3 km) from Windham Mountain Resort and 1.3 mi (2.1 km) from Windham Country Club. Windham Vineyards ...

                    Beds on Clouds$109

                    Beds on Clouds$109
                    Catskill Lodge

                    Catskill Lodge

                    350 NY State Route 296, Windham
                      3.0 out of 5.0
                       
                       

                      Situated in Windham, this bed & breakfast is 1.2 mi (2 km) from Windham Country Club and 2.5 mi (4.1 km) from Windham Mountain Resort. Windham Vineyards and ...

                      Catskill Lodge$127

                      Catskill Lodge$127

                      Top Flight Deals

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