Windham Rentals Are Going Fast in Windham, Catskills, New York

Known as one of the 20 wildest, tastiest mountain communities in America, Windham, NY is the only spot to be for your winter vacation. You will have so much fun you will want to book for the summer too!

Book One of the Windham Rentals Today


Because they are found in a hot vacation spot, Windham rentals are in high demand. Check the availability of Windham vacation rentals easily and be sure to book that vacation spot early.

Popular Windham cottages at the foot of Windham Mountain put you in clear view of ski conditions right outside the large windows. You will know right away if you should strap on those skis or nestle back into the comfortable bed!

Windham Vacation Rentals Save Your Vacation Dollars


Face it: with economic times as they are, it can be hard to take a vacation. Windham rentals open up a world of luxurious choices at extremely reasonable rates. Save money by booking Windham vacation rentals and you have plenty left over to browse through the treasure shops lining our wide streets.

Windham cottages provide luxury accommodations at rock-bottom prices. You can have the vacation of your dreams without leaving all your hard-earned money behind.

Establish Your Base Camp in Windham Cottages


Whether you are hunting birds and beasts or bargains, Windham rentals are perfect base camps. Spread out in our large living spaces and get comfy in our fully-equipped kitchens, then venture out to enjoy golf, fishing, art galleries, and the historic sights and sounds of the town. You might get so comfortable you don’t want to leave your Windham vacation rentals. You will be thrilled by the million-dollar views from Windham cottages, no matter what time of year you choose to visit. They do book up early, so book a prime location today and get started on the vacation of your dreams!

When looking for Catskills cabins, be sure to look into these other options in the area: Andes apartments, Belleayre Mountain cabins, Delaware River Valley cabins, Hunter Mountain condos and Woodstock cottages.

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Windham: Houses, Cabins & More(80)

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Luxury Log Home with Ski Windham views
    4 Bedrooms,
  • 4 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 14
$800 - $2,500
per night

Luxury Log Home with Ski Windham views

2 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
  1. Catskills >
  2. Windham Estate
#155527
    (29)
    Charming log cabin on 75 private beautiful acres,4 miles to windham ski and golf
      5 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 10
    $500
    per night

    Charming log cabin on 75 private beautiful acres,4 miles to windham ski and golf

    2 night minimum stay
    • 5 BR,
    • 3 BA,
    • Sleeps 10
    1. Catskills >
    2. Windham Cabin
    #920655
      (7)
      Private Rental Estate+Beautiful Horses/Swim onsite/Great covered Deck/Pets OK
        5 Bedrooms, Sleeps 12

      Private Rental Estate+Beautiful Horses/Swim onsite/Great covered Deck/Pets OK

      • 5 BR,
      • Sleeps 12
      1. Catskills >
      2. Windham Estate
      #72220vb
        (18)
        Windham Ski Cabin w/ Sauna 1 Mi from center of town
          4 Bedrooms,
        • 2 Bathrooms
          • , Sleeps 13

        Windham Ski Cabin w/ Sauna 1 Mi from center of town

        • 4 BR,
        • 2 BA,
        • Sleeps 13
        1. Catskills >
        2. Windham Cabin
        #251243
          (15)
          4 bedroom Windham Ski Vacation House, outdoor hot-tub sleeps 6-12
            4 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 14
          $225 - $499
          per night

          4 bedroom Windham Ski Vacation House, outdoor hot-tub sleeps 6-12

          2 night minimum stay
          • 4 BR,
          • 2 BA,
          • Sleeps 14
          1. Catskills >
          2. Windham House
          #113830
            (21)
            Make The Inn at Hill Crest Manor Your Personal Country Mansion!
              5 Bedrooms,
            • 6 Bathrooms, 
            • 1 Half Bath
              • , Sleeps 12
            $500 - $600
            per night

            Make The Inn at Hill Crest Manor Your Personal Country Mansion!

            2 night minimum stay
            • 5 BR,
            • 6 BA,
            • 1 HF BA,
            • Sleeps 12
            1. Catskills >
            2. Windham Chateau / Country House
            #283517
              2 Reviews
              Great Windham House On 5 Private Acres: Pond, Hot Tub, Fire Pit, Grill
                3 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 10
              $375 - $450
              per night

              Great Windham House On 5 Private Acres: Pond, Hot Tub, Fire Pit, Grill

              2 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 10
              1. Catskills >
              2. Windham House
              #3320311
                (4)
                Quaint Cabin Minutes from Ski Slopes and Great State Parks
                  2 Bedrooms,
                • 1 Bathroom
                  • , Sleeps 4
                $400 - $500
                per week

                Quaint Cabin Minutes from Ski Slopes and Great State Parks

                2 night minimum stay
                • 2 BR,
                • 1 BA,
                • Sleeps 4
                1. Catskills >
                2. Windham Cabin
                #268457
                  (4)
                  Windham Family Funhouse and Nature Retreat
                    5 Bedrooms,
                  • 2 Bathrooms, 
                  • 1 Half Bath
                    • , Sleeps 15

                  Windham Family Funhouse and Nature Retreat

                  • 5 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 15
                  1. Catskills >
                  2. Windham
                  #243448
                    (16)
                    Charming Lake home, perfect for all seasons!
                      4 Bedrooms,
                    • 3 Bathrooms
                      • , Sleeps 8

                    Charming Lake home, perfect for all seasons!

                    • 4 BR,
                    • 3 BA,
                    • Sleeps 8
                    1. Catskills >
                    2. Windham Chalet
                    #385951
                      Catskills, Windham Ski Area
                        4 Bedrooms,
                      • 3 Bathrooms
                        • , Sleeps 10
                      $200 - $400
                      per night

                      Catskills, Windham Ski Area

                      2 night minimum stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 10
                      1. Catskills >
                      2. Windham House
                      #174521
                        (9)
                        Cool Summer Days @ Windham Cabin in the Sky, 6 adults + 1 child
                          3 Bedrooms,
                        • 2 Bathrooms
                          • , Sleeps 7
                        $175 - $330
                        per night

                        Cool Summer Days @ Windham Cabin in the Sky, 6 adults + 1 child

                        Book it Now!
                        3 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 7
                        1. Catskills >
                        2. Windham Cabin
                        #914098
                          (4)
                          Cozy home close to Windham and Hunter Mountain
                            3 Bedrooms,
                          • 1 Bathroom, 
                          • 1 Half Bath
                            • , Sleeps 6
                          $145 - $275
                          per night

                          Cozy home close to Windham and Hunter Mountain

                          Book it Now!
                          2 night minimum stay
                          • 3 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 6
                          1. Catskills >
                          2. Windham House
                          #953111
                            (4)
                            Cozy & Secluded Catskill Ski Chalet Perfect For Every Season
                              3 Bedrooms,
                            • 3 Bathrooms
                              • , Sleeps 8
                            $280 - $375
                            per night

                            Cozy & Secluded Catskill Ski Chalet Perfect For Every Season

                            • 3 BR,
                            • 3 BA,
                            • Sleeps 8
                            1. Catskills >
                            2. Windham Chalet
                            #330463
                              (16)
                              Catskill Bungalow -Cozy Vacation Cabin for up to 3, Windham & Hunter
                                1 Bedrooms,
                              • 1 Bathroom
                                • , Sleeps 3
                              $65 - $89
                              per night

                              Catskill Bungalow -Cozy Vacation Cabin for up to 3, Windham & Hunter

                              2 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 3
                              1. Catskills >
                              2. Windham Cabin
                              #242542
                                1 Review
                                Contemporary Chalet, 1.5 miles to Ski Windham.
                                  4 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 8
                                $75 - $325
                                per night

                                Contemporary Chalet, 1.5 miles to Ski Windham.

                                2 night minimum stay
                                • 4 BR,
                                • 2 BA,
                                • Sleeps 8
                                1. Catskills >
                                2. Windham Chalet
                                #129642
                                  (5)
                                  Charming Country Cabin
                                    4 Bedrooms,
                                  • 2 Bathrooms
                                    • , Sleeps 10
                                  $150 - $6,500
                                  per night

                                  Charming Country Cabin

                                  2 night minimum stay
                                  • 4 BR,
                                  • 2 BA,
                                  • Sleeps 10
                                  1. Catskills >
                                  2. Windham Cabin
                                  #252461
                                    House For Rent Catskill Windham and Hunter mt.
                                      4 Bedrooms,
                                    • 2 Bathrooms, 
                                    • 1 Half Bath
                                      • , Sleeps 12
                                    $150 - $400
                                    per night

                                    House For Rent Catskill Windham and Hunter mt.

                                    • 4 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 12
                                    1. Catskills >
                                    2. Windham House
                                    #222672
                                      (8)
                                      Scenic Catskill Mountains Cottage for Spring, summer and autumn rental
                                        1 Bedrooms,
                                      • 1 Bathroom
                                        • , Sleeps 2
                                      $90 - $120
                                      per night

                                      Scenic Catskill Mountains Cottage for Spring, summer and autumn rental

                                      2 night minimum stay
                                      • 1 BR,
                                      • 1 BA,
                                      • Sleeps 2
                                      1. Catskills >
                                      2. Windham Cottage
                                      #193113
                                        (3)
                                        SPECIAL for 2 people with Hot Tub
                                          3 Bedrooms,
                                        • 1 Bathroom, 
                                        • 1 Half Bath
                                          • , Sleeps 8
                                        $150
                                        per night

                                        SPECIAL for 2 people with Hot Tub

                                        2 night minimum stay
                                        • 3 BR,
                                        • 1 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                        1. Catskills >
                                        2. Windham Townhome
                                        #943102
                                          (9)
                                          4bedroom Elegant, spacious, new home
                                            4 Bedrooms,
                                          • 2 Bathrooms
                                            • , Sleeps 10
                                          $150 - $200
                                          per night

                                          4bedroom Elegant, spacious, new home

                                          2 night minimum stay
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 10
                                          1. Catskills >
                                          2. Windham House
                                          #257700
                                            (27)
                                            Comfortable Victorian Home In The Village Of Windham
                                              4 Bedrooms,
                                            • 2 Bathrooms
                                              • , Sleeps 8
                                            $150 - $500
                                            per night

                                            Comfortable Victorian Home In The Village Of Windham

                                            2 - 3 night minimum stay
                                            • 4 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                            1. Catskills >
                                            2. Windham House
                                            #3478292
                                              1 Review
                                              — Escape from reality luxury cabin retreat in the Catskills
                                                3 Bedrooms,
                                              • 2 Bathrooms, 
                                              • 1 Half Bath
                                                • , Sleeps 10
                                              $100 - $200
                                              per night

                                              — Escape from reality luxury cabin retreat in the Catskills

                                              2 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 10
                                              1. Catskills >
                                              2. Windham Chalet
                                              #3472034
                                                1 Review
                                                A hop, skip and a jump to Windham and Hunter Mountains!
                                                  6 Bedrooms,
                                                • 3 Bathrooms
                                                  • , Sleeps 14
                                                $300 - $1,200
                                                per night

                                                A hop, skip and a jump to Windham and Hunter Mountains!

                                                2 night minimum stay
                                                • 6 BR,
                                                • 3 BA,
                                                • Sleeps 14
                                                1. Catskills >
                                                2. Windham Chalet
                                                #225059
                                                  2 Reviews
                                                  Mountain house retreat with panoramic views & fresh water pond
                                                    4 Bedrooms,
                                                  • 2 Bathrooms
                                                    • , Sleeps 9
                                                  $230 - $300
                                                  per night

                                                  Mountain house retreat with panoramic views & fresh water pond

                                                  2 - 151 night minimum stay
                                                  • 4 BR,
                                                  • 2 BA,
                                                  • Sleeps 9
                                                  1. Catskills >
                                                  2. Windham House
                                                  #914873
                                                    2 Reviews
                                                    Family Friendly Mountainside Get-A-Way Chalet. A Four Season Retreat.
                                                      3 Bedrooms,
                                                    • 1 Bathroom
                                                      • , Sleeps 8
                                                    $350
                                                    per night

                                                    Family Friendly Mountainside Get-A-Way Chalet. A Four Season Retreat.

                                                    2 night minimum stay
                                                    • 3 BR,
                                                    • 1 BA,
                                                    • Sleeps 8
                                                    1. Catskills >
                                                    2. Windham Chalet
                                                    #3520172
                                                      2 Reviews
                                                      Beautiful, Private, Luxurious Escape from the City!
                                                        4 Bedrooms,
                                                      • 2 Bathrooms
                                                        • , Sleeps 10

                                                      Beautiful, Private, Luxurious Escape from the City!

                                                      • 4 BR,
                                                      • 2 BA,
                                                      • Sleeps 10
                                                      1. Catskills >
                                                      2. Windham Estate
                                                      #184886
                                                        (5)
                                                        Tuscan Year Round Beauty 1-3 Families - Weddings / Gatherings - outdoor kitchen
                                                          6 Bedrooms,
                                                        • 3 Bathrooms
                                                          • , Sleeps 14

                                                        Tuscan Year Round Beauty 1-3 Families - Weddings / Gatherings - outdoor kitchen

                                                        • 6 BR,
                                                        • 3 BA,
                                                        • Sleeps 14
                                                        1. Catskills >
                                                        2. Windham House
                                                        #172309
                                                          (11)
                                                          Cozy Cottage For Two Or Two Couples
                                                            2 Bedrooms,
                                                          • 1 Bathroom
                                                            • , Sleeps 6
                                                          $135 - $175
                                                          per night

                                                          Cozy Cottage For Two Or Two Couples

                                                          2 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 6
                                                          1. Catskills >
                                                          2. Windham Cottage
                                                          #436777vb
                                                            1 Review
                                                            Cutest Cabin with air conditioning for 2 people
                                                              1 Bedrooms,
                                                            • 1 Bathroom
                                                              • , Sleeps 2
                                                            $125
                                                            per night

                                                            Cutest Cabin with air conditioning for 2 people

                                                            2 night minimum stay
                                                            • 1 BR,
                                                            • 1 BA,
                                                            • Sleeps 2
                                                            1. Catskills >
                                                            2. Windham Cabin
                                                            #3477551
                                                              1 Review
                                                              • 1 - 30 of 80
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