Vacation Rentals & Timeshares in Windham

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204 timeshares

    10

    Beautiful mountain lodge home

    Catskill Region / Windham

    Windham house

    3 8 1 night min

    • 3 bedrooms
    • sleeps 8
    • 1 night min
    • Child Friendly
    • Air conditioning
    • Pet Friendly

    Price per night from

    $373

    Price per night from

    $373

    (22) Excellent 

    Certificate of Excellence

      45

      Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain

      Catskill Region / Windham

      Windham house

      2 6 min stay varies

      • 2 bedrooms
      • sleeps 6
      • min stay varies
      • Car not necessary
      • Air conditioning
      • Private garden
      “Home away from home” My sisters and I rented this cottage on Labor day weekend for our annual sisters get away. Ella was very helpful giving exact directions to the cabin which is important when you are not familiar with a location. She was able to
      …see more

      Certificate of Excellence

      Price per night from

      $86

      Responds fast!
      avg. 2 hours 16 minutes

      Price per night from

      $86

      (4) Excellent 

        53

        Secluded Charming Water Front Log Home

        Catskill Region / Windham

        Windham house

        4 15 2 nights min

        • 4 bedrooms
        • sleeps 15
        • 2 nights min
        • Ski
        • Child Friendly
        • Private garden

        Price per night from

        $343

        Price per night from

        $343

        (39) Excellent 

        Certificate of Excellence

          38

          Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham

          Catskill Region / Windham

          Windham log cabin

          1 2 min stay varies

          • 1 bedroom
          • sleeps 2
          • min stay varies
          • Car not necessary
          • Air conditioning
          “Best weekend ever :)” I have recently rented the bungalow and just have great things to say about it. The place is so cozy, and cute, they had everything we needed and the location couldn't be better. It's very close to any of the skii resorts and man
          …see more

          Certificate of Excellence

          Price per night from

          $81

          Responds fast!
          avg. 2 hours 16 minutes

          Price per night from

          $81

          (1) Excellent 

            26

            ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

            Catskill Region / Windham

            Windham house

            2 5 2 nights min

            • 2 bedrooms
            • sleeps 5
            • 2 nights min
            • Child Friendly
            • Pet Friendly

            Price per night from

            $201

            Responds fast!
            avg. 2 hours 2 minutes

            Price per night from

            $201

              20

              Windham Mountain Ski House with Great Views

              Catskill Region / Windham

              Windham house

              3 8 2 nights min

              • 3 bedrooms
              • sleeps 8
              • 2 nights min
              • Child Friendly

              Price per night from

              $401

              Price per night from

              $401

                24

                Two-Story, 3-Bedroom Family Home

                Catskill Region / Windham

                Windham house

                3 4 2 nights min

                • 3 bedrooms
                • sleeps 4
                • 2 nights min
                • Child Friendly
                • Private garden

                Price per night from

                $229

                Price per night from

                $229

                  34

                  The Mountain House: The Perfect 4 Season Retreat

                  Catskill Region / Windham

                  Windham chalet

                  8 22 3 nights min

                  • 8 bedrooms
                  • sleeps 22
                  • 3 nights min
                  • Ski
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $2,930

                  Responds fast!
                  avg. 3 hours 28 minutes

                  Price per night from

                  $2,930

                    45

                    Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.

                    Catskill Region / Windham

                    Windham house

                    4 10 2 nights min

                    • 4 bedrooms
                    • sleeps 10
                    • 2 nights min
                    • Ski
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $630

                    Price per night from

                    $630

                      16

                      A Stunning Upstate NY Property

                      Catskill Region / Windham

                      Windham house

                      4 8 2 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 2 nights min
                      • Child Friendly
                      • Pet Friendly

                      Price per night from

                      $879

                      Price per night from

                      $879

                        31

                        NEW! Sleek 4BR Windham House w/Hot Tub & Mtn Views

                        Catskill Region / Windham

                        Windham house

                        4 10 min stay varies

                        • 4 bedrooms
                        • sleeps 10
                        • min stay varies
                        • Child Friendly
                        • Ask about pets

                        Price per night from

                        $528

                        Responds fast!
                        avg. 9 minutes

                        Price per night from

                        $528

                        (37) Excellent 

                        Certificate of Excellence

                          24

                          *4SeasonNirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw

                          Catskill Region / Windham

                          Windham house

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Nearest beach 29 mi
                          • Child Friendly
                          • Air conditioning
                          “Terrific Rental in Windham” This is a great rental property. The house is very well maintained and comes complete with everything you need for your visit. This includes the kitchen where many other rental properties offer sparse and/or low quality ut
                          …see more

                          Certificate of Excellence

                          Price per night from

                          $206

                          Responds fast!
                          avg. 36 minutes

                          Price per night from

                          $206

                          (5) Excellent 

                            18

                            Mountain House Retreat:Let It Snow! Book Now! Over 1 Foot Of Fresh Powdered Snow

                            Catskill Region / Windham

                            Windham house

                            5 10 2 nights min

                            • 5 bedrooms
                            • sleeps 10
                            • 2 nights min
                            • Child Friendly
                            • Pet Friendly
                            • Private garden
                            “Beautiful! Relaxing! Perfect!” I spent 4th of July weekend with a group of friends at this wonderful mountain retreat, and it was all that we wished and more!! The views are spectacular, the private pond and the mountains added so much to our stay.
                            …see more

                            Price per night from

                            $352

                            Price per night from

                            $352

                              12

                              Chickadee Chalet

                              Catskill Region / Windham

                              Windham apartment

                              2 4 2 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 2 nights min
                              • Ski

                              Price per night from

                              $401

                              Price per night from

                              $401

                                9

                                Windham Mountain Ski House

                                Catskill Region / Windham

                                Windham house

                                5 10 90 nights min

                                • 5 bedrooms
                                • sleeps 10
                                • 90 nights min
                                • Child Friendly
                                • Private garden

                                Price per night from

                                $571

                                Price per night from

                                $571

                                (2) Excellent 

                                  23

                                  The Catskills Tranquility House

                                  Catskill Region / Windham

                                  Windham house

                                  3 10 2 nights min

                                  • 3 bedrooms
                                  • sleeps 10
                                  • 2 nights min
                                  • Beach / lakeside relaxation
                                  • Ski
                                  • Child Friendly

                                  Price per night from

                                  $344

                                  Price per night from

                                  $344

                                  (4) Very Good 

                                    20

                                    Country Convenient 2, 2bd townhouse Windham Hunter

                                    Catskill Region / Windham

                                    Windham townhouse

                                    2 4 2 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 2 nights min
                                    • Child Friendly

                                    Price per night from

                                    $98

                                    Responds fast!
                                    avg. 2 hours 45 minutes

                                    Price per night from

                                    $98

                                    (1) Excellent 

                                      9

                                      The Presidential Suite at Brie & Bordeaux

                                      Catskill Region / Windham

                                      Windham apartment

                                      3 6 2 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 2 nights min
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $485

                                      Price per night from

                                      $485

                                      (4) Excellent 

                                        76

                                        Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!

                                        Catskill Region / Windham

                                        Windham tented camp

                                        1 4 min stay varies

                                        • 1 bedroom
                                        • sleeps 4
                                        • min stay varies
                                        • Car not necessary
                                        • Air conditioning

                                        Price per night from

                                        $101

                                        Responds fast!
                                        avg. 2 hours 16 minutes

                                        Price per night from

                                        $101

                                          24

                                          The Xenia

                                          Catskill Region / Windham

                                          Windham house

                                          4 16 2 nights min

                                          • 4 bedrooms
                                          • sleeps 16
                                          • 2 nights min
                                          • Child Friendly

                                          Price per night from

                                          $571

                                          Price per night from

                                          $571

                                          (1) Excellent 

                                            14

                                            Beautiful apartment with great views!

                                            Catskill Region / Windham

                                            Windham apartment

                                            2 4 2 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 2 nights min
                                            • Child Friendly
                                            • Private garden

                                            Price per night from

                                            $235

                                            Responds fast!
                                            avg. 3 hours 46 minutes

                                            Price per night from

                                            $235

                                            (4) Very Good 

                                              18

                                              Mountain Treasure Cottage, WIndham, NY

                                              Catskill Region / Windham

                                              Windham cottage

                                              2 8 2 nights min

                                              • 2 bedrooms
                                              • sleeps 8
                                              • 2 nights min
                                              • Child Friendly
                                              • Car not necessary
                                              • Air conditioning

                                              Price per night from

                                              $286

                                              Responds fast!
                                              avg. 2 hours 47 minutes

                                              Price per night from

                                              $286

                                                8

                                                Cristal pound at Windham ski resort

                                                Catskill Region / Windham

                                                Windham condo

                                                4 10 4 nights min

                                                • 4 bedrooms
                                                • sleeps 10
                                                • 4 nights min

                                                Price per night from

                                                $235

                                                Price per night from

                                                $235

                                                (3) Excellent 

                                                  21

                                                  Amazing Mountain Views, Total Privacy

                                                  Catskill Region / Windham

                                                  Windham house

                                                  4 13 2 nights min

                                                  • 4 bedrooms
                                                  • sleeps 13
                                                  • 2 nights min
                                                  • Child Friendly
                                                  • Air conditioning
                                                  • Private garden

                                                  Price per night from

                                                  $331

                                                  Price per night from

                                                  $331

                                                  (3) Excellent 

                                                    54

                                                    WINDHAM MAGNIFICENT HOLIDAY GETAWAY

                                                    Catskill Region / Windham

                                                    Windham house

                                                    5 18 2 nights min

                                                    • 5 bedrooms
                                                    • sleeps 18
                                                    • 2 nights min
                                                    • Ski
                                                    • Child Friendly

                                                    Price per night from

                                                    $1,054

                                                    Price per night from

                                                    $1,054

                                                    (6) Excellent 

                                                      39

                                                      Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental

                                                      Catskill Region / Windham

                                                      Windham apartment

                                                      1 3 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • min stay varies
                                                      • Car not necessary
                                                      • Air conditioning

                                                      Price per night from

                                                      $79

                                                      Responds fast!
                                                      avg. 2 hours 16 minutes

                                                      Price per night from

                                                      $79

                                                        24

                                                        NEW! Cozy Windham Condo w/ Pool & Tennis Courts!

                                                        Catskill Region / Windham

                                                        Windham apartment

                                                        1 4 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Ski
                                                        • Child Friendly

                                                        Price per night from

                                                        $149

                                                        Responds fast!
                                                        avg. 36 minutes

                                                        Price per night from

                                                        $149

                                                        (2) Excellent 

                                                          29

                                                          Restored Firehouse w/Theater 1mi to Windham Mtn!

                                                          Catskill Region / Windham

                                                          Windham townhouse

                                                          4 16 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 16
                                                          • min stay varies
                                                          • Ski
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $802

                                                          Responds fast!
                                                          avg. 36 minutes

                                                          Price per night from

                                                          $802

                                                            24

                                                            NEW! Catskills Area Loft-Style Condo in Downtown!

                                                            Catskill Region / Windham

                                                            Windham studio

                                                            Studio 6 min stay varies

                                                            • Studio
                                                            • sleeps 6
                                                            • min stay varies
                                                            • Ski
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $183

                                                            Responds fast!
                                                            avg. 36 minutes

                                                            Price per night from

                                                            $183

                                                              45

                                                              'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!

                                                              Catskill Region / Windham

                                                              Windham house

                                                              12 33 min stay varies

                                                              • 12 bedrooms
                                                              • sleeps 33
                                                              • min stay varies
                                                              • Ski
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $1,947

                                                              Responds fast!
                                                              avg. 36 minutes

                                                              Price per night from

                                                              $1,947

                                                                26

                                                                NEW! Spacious House - 1 Mi. to Windham Ski Resort!

                                                                Catskill Region / Windham

                                                                Windham house

                                                                5 13 min stay varies

                                                                • 5 bedrooms
                                                                • sleeps 13
                                                                • min stay varies
                                                                • Ski
                                                                • Child Friendly

                                                                Price per night from

                                                                $172

                                                                Responds fast!
                                                                avg. 36 minutes

                                                                Price per night from

                                                                $172

                                                                (1) Excellent 

                                                                  39

                                                                  Amazing 4 BR on Windham

                                                                  Catskill Region / Windham

                                                                  Windham villa

                                                                  4 8 2 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 2 nights min
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  Price per night from

                                                                  $315

                                                                  Price per night from

                                                                  $315

                                                                  Great rentals within 20 miles that match your search

                                                                  Distance approx 7.83 km from Windham Show on Map

                                                                  (1) Excellent 

                                                                    16

                                                                    Lovely country home in the Catskills

                                                                    Durham / East Durham

                                                                    East Durham house

                                                                    4 8 2 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • 2 nights min
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $352

                                                                    Responds fast!
                                                                    avg. 2 hours 54 minutes

                                                                    Price per night from

                                                                    $352

                                                                    Distance approx 19.44 km from Windham Show on Map

                                                                    (3) Excellent 

                                                                      29

                                                                      Margaret's Cottage in Woodstock Village

                                                                      Catskill Region / Woodstock

                                                                      Woodstock log cabin

                                                                      2 4 2 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Car not necessary
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $194

                                                                      Price per night from

                                                                      $194

                                                                      Distance approx 16.91 km from Windham Show on Map

                                                                      (12) Excellent 

                                                                      Certificate of Excellence

                                                                        17

                                                                        Mountain Top Retreat, 116 private acres

                                                                        Catskill Region / Hobart

                                                                        Hobart house

                                                                        2 6 2 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • 2 nights min
                                                                        • Child Friendly
                                                                        • Private garden
                                                                        “The most peaceful vacation I have ever had!” The house is totally secluded and very pretty on the inside. All we needed to bring with us were clothes and food, the house had everything else we could have needed and a lot more. We brought our three chi
                                                                        …see more

                                                                        Certificate of Excellence

                                                                        Price per night from

                                                                        $176

                                                                        Responds fast!
                                                                        avg. 3 hours 6 minutes

                                                                        Price per night from

                                                                        $176

                                                                        Distance approx 10.95 km from Windham Show on Map

                                                                        (6) Very Good 

                                                                          10

                                                                          Cozy Cottage

                                                                          Catskill Region / Hunter

                                                                          Hunter cottage

                                                                          2 4 2 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 2 nights min
                                                                          • Nearest beach 2 mi
                                                                          • Child Friendly
                                                                          • Private garden

                                                                          Price per night from

                                                                          $176

                                                                          Responds fast!
                                                                          avg. 3 hours 20 minutes

                                                                          Price per night from

                                                                          $176

                                                                          Distance approx 17.84 km from Windham Show on Map

                                                                            12

                                                                            Blue Mountain Guest House

                                                                            Catskill Region / Saugerties

                                                                            Saugerties cottage

                                                                            1 4 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            • Air conditioning
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $264

                                                                            Price per night from

                                                                            $264

                                                                            Distance approx 18.65 km from Windham Show on Map

                                                                              28

                                                                              Relaxing Zen Cabin

                                                                              Catskill Region / Woodstock

                                                                              Woodstock house

                                                                              1 4 min stay varies

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $184

                                                                              Price per night from

                                                                              $184

                                                                              About Windham

                                                                              Known to Native Americans as 'The Land in the Sky', Windham is perfect for the outdoor enthusiast. With nature and activities at the heart of the town, you'll have plenty to do and see. Book your Windham vacation rental with FlipKey today.

                                                                              About Windham

                                                                              Windham is a town located in Greene County and was first settled in around 1780. These days, locals gain their main source of income from the ski resort in the Windham mountains, which attracts tourists from the New York area three hours away. It features 54 trails and 12 lifts, with its highest peak at 3,100 feet.

                                                                              If you fancy trekking around the rivers and streams, you'll be sure to find a large variety of fish and other wildlife, such as deer and turkeys.

                                                                              What to do

                                                                              As mentioned, Windham Mountain Resort is the main reason why tourists travel to this particular town in New York. With ninety-seven percent snow coverage, you'll have the best possible snow conditions to make the most of your trip. This activity would definitely be for thrill-seekers looking to add another cool activity to their bucket-list!

                                                                              There's also an adventure park at Windham Mountain—another exciting experience for those looking for active pursuits. Here, you can have a go on a high zip-line, try off-road go-karting, trampolines and even test your skills at a skate park.

                                                                              You may even decide to take a trip to Windham Golf Club where you can play on an 18-hole golf course. This charming course in the picturesque Catskills was designed in 1928.

                                                                              While there's plenty to keep outdoors enthusiasts occupied, there's also the option to completely chill-out. The town is filled with relaxing spas which offer several treatments, so you can feel fully refreshed after a tiring day.

                                                                              Top travel tips

                                                                              To get around Windham, use a car—there are no major public transport. This is especially relevant if you wish to go to the Windham Mountain due to the remoteness of the area.

                                                                              There are bike rentals you can hire for your vacation, which is perfect if you wish to explore more of the area.

                                                                              The weather in Windham is fairly cool all year round, which is to be expected of a snow resort! In the months of January and February, temperatures can reach lows of -1 degree Fahrenheit.

                                                                              Take a trip to Windham this year for an outdoor adventure you'll never forget. Packed with active pursuits and relaxing scenic views, this small town is definitely worth the visit. Book your Windham rental with FlipKey and experience it for yourself.