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Windham Vacation Travel Guide

Vacationing is good for the soul. It lets you rest, relax, recharge, and refresh, so you’re ready to take on new endeavors when you return home. When it’s time to let loose and embark on a group adventure or unwind and rejuvenate on a solo sojourn, turn to Expedia for major discounts on Windham vacation packages.

It’s easy to book the getaway of your dreams when you search through our selection of Windham vacations. Our goal? To create the perfect trip for you by providing the largest selection of vacation packages. Confidently book your getaway thanks to our trustworthy recommendations and verified consumer reviews from travelers just like you. Personalize your Windham package with our myriad of hotel rooms and flight tickets, which help to create a vacation specifically for you. Simply sort through our selection and pick and choose the elements that best suit your preferences and price range.

Because we offer the best rates, you can book your travel reservations knowing you won’t find lower prices elsewhere. These discounts are so great, you’ll feel like you gained the title of the ultimate bargain hunter with our Windham vacation package deals. Whether you’re looking to book multiple flights, stay at the fanciest hotel, or explore the hottest local attractions, you’ll find discounted travel arrangements within your budget right here. You shouldn’t have a care in the world when you go on vacation, so our discounts allow you to rest easy without giving your bank account a second thought. Save money on your vacation today and revel in your much-deserved getaway tomorrow.


Top Hotel Deals

See all 176 Properties in Windham
Antique Rose Inn Windham
Antique Rose Inn Windham

Antique Rose Inn Windham

326 State Route 296, Windham
     
    4.7
    of 5, from 21 reviews
    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 is 8.4 mi (13.6 km) away.

    Hotel Vienna
    Hotel Vienna

    Hotel Vienna

    107 State Route 296, Windham
       
      4.5
      of 5, from 75 reviews
      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 Hunter Mountain are also within 9 mi (15 km).

      Winwood Inn & Condominiums $114
      Winwood Inn & Condominiums

      Winwood Inn & Condominiums

      5220 NY-23, Windham
         
        4.0
        of 5, from 52 reviews
        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 close to winter sports such as cross-country skiing and skiing lessons. Hunter Mountain and Zoom Flume are also within 12 mi (20 km).

        Cave Mountain Motel $89
        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 Zoom Flume are also within 12 mi (20 km).

          The Thompson House
          The Thompson House

          The Thompson House

          19 Rt. 296, Windham
             
            4.0
            of 5, from 19 reviews
            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 Winery and Hunter Mountain are also within 9 mi (15 km).

            Georgian Garden Inn
            Georgian Garden Inn

            Georgian Garden Inn

            5159 state route 23, Windham
               
              4.6
              of 5, from 7 reviews
              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 and Winery and Hunter Mountain are also within 12 mi (20 km).

              Luxury Log Home With Ski Windham Views
              Luxury Log Home With Ski Windham Views

              Luxury Log Home With Ski Windham Views

              , Windham
                 
                5.0
                of 5, from 12 reviews
                0.0 out of 5.0

                Situated in Windham, this historic vacation home is 1.3 mi (2.1 km) from Windham Country Club and 2.5 mi (3.9 km) from Windham Mountain Resort. Windham Vineyards and Winery and Hunter Mountain are also within 12 mi (20 km).

                New! 5BR Windham Home W/game Room, Hot Tub & Views
                New! 5BR Windham Home W/game Room, Hot Tub & Views

                New! 5BR Windham Home W/game Room, Hot Tub & Views

                , Windham
                   
                  5.0
                  of 5, from 1 reviews
                  0.0 out of 5.0

                  Set in Windham, this family-friendly vacation home is within 6 mi (10 km) of Windham Mountain Resort, Windham Country Club, and Windham Vineyards and Winery. Zoom Flume is 7.1 mi (11.4 km) away.