Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Cabins
Chalets
Condos
Cottages
Estates
Farmhouses
Homes
Lodges
Studios
Townhomes
Barns
Boats
Bungalows
Castles
Hotels
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Windham Vacation Rentals with Parking Included(79)

79 Results
Book it Now!
2 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
    (16)
    Book it Now!
    2 - 3 night minimum stay
    • 4 BR,
    • 3 BA,
    • Sleeps 14
      (17)
      2 night minimum stay
      • 5 BR,
      • 3 BA,
      • Sleeps 10
        (13)
        Book it Now!
        2 night minimum stay
        • 4 BR,
        • 3 BA,
        • Sleeps 16
          1 Review
          2 night minimum stay
          • 4 BR,
          • 4 BA,
          • 1 HF BA,
          • Sleeps 14
            (30)
            • 3 BR,
            • 2 BA,
            • Sleeps 10
              2 Reviews
              2 night minimum stay
              • 7 BR,
              • 5 BA,
              • 1 HF BA,
              • Sleeps 14
                Book it Now!
                3 - 7 night minimum stay
                • 2 BR,
                • 1 BA,
                • 1 HF BA,
                • Sleeps 8
                  (6)
                  Book it Now!
                  2 night minimum stay
                  • 8 BR,
                  • 6 BA,
                  • 1 HF BA,
                  • Sleeps 22
                    2 night minimum stay
                    • 3 BR,
                    • 1 BA,
                    • Sleeps 6
                      (6)
                      • 5 BR,
                      • 5 BA,
                      • Sleeps 12
                        Book it Now!
                        • 2 BR,
                        • 1 BA,
                        • Sleeps 5
                          Book it Now!
                          2 night minimum stay
                          • 4 BR,
                          • 2 BA,
                          • Sleeps 9
                            Book it Now!
                            2 night minimum stay
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 12
                              2 night minimum stay
                              • 3 BR,
                              • 1 BA,
                              • Sleeps 8
                                Book it Now!
                                3 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 7
                                  (6)
                                  2 night minimum stay
                                  • 5 BR,
                                  • 6 BA,
                                  • 1 HF BA,
                                  • Sleeps 12
                                    (7)
                                    2 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 10
                                      (13)
                                      2 night minimum stay
                                      • 3 BR,
                                      • 1 BA,
                                      • Sleeps 6
                                        (4)
                                        2 night minimum stay
                                        • 4 BR,
                                        • 3 BA,
                                        • Sleeps 10
                                          • 5 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 15
                                            (22)
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                              Book it Now!
                                              2 - 4 night minimum stay
                                              • 5 BR,
                                              • 3 BA,
                                              • 1 HF BA,
                                              • Sleeps 17
                                                Book it Now!
                                                2 - 3 night minimum stay
                                                • 4 BR,
                                                • 3 BA,
                                                • Sleeps 10
                                                  (15)
                                                  Book it Now!
                                                  • 1 BR,
                                                  • 1 BA,
                                                  • Sleeps 3
                                                    2 Reviews
                                                    2 night minimum stay
                                                    • 3 BR,
                                                    • 3 BA,
                                                    • Sleeps 8
                                                      (18)
                                                      Book it Now!
                                                      2 - 5 night minimum stay
                                                      • 4 BR,
                                                      • 2 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 12
                                                        (3)
                                                        Book it Now!
                                                        2 - 3 night minimum stay
                                                        • 4 BR,
                                                        • 2 BA,
                                                        • Sleeps 10
                                                          2 Reviews
                                                          $175
                                                          per night
                                                          Book it Now!
                                                          2 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 6
                                                            2 night minimum stay
                                                            • 5 BR,
                                                            • 2 BA,
                                                            • Sleeps 12
                                                              (7)
                                                              Advertisement
                                                               

                                                              Recent Windham Reviews

                                                              Couldn't be any better!

                                                              5 of 5
                                                              Aside from amazing, I'm not sure what else I could say about this house. For starters, the owners were a joy to deal with. Not only did they respond promptly to my inquiry (I was all booked and set to go within an hour), but they accommodated my last minute reservation without any hassles or issues. Even though it was a holiday weekend, our questions were answered promptly all throughout our stay. As for the house... wow!! It was beyond comfortable. It was spotless, roomy, and in a great location. There were no bugs hanging out, no spider webs, no ants, no dusty furniture. I'm ashamed to say that it was cleaner than our own house. It's decorated and furnished in such a way that it truly feels like a home away from home. The pool table and the board games were a nice addition, especially during one of the days when it rained. The giant flat screen TV with surround sound was perfect for movies (and to watch the Mets lose again. *sigh*) The yard is huge and allows for room to do just about anything. We had a family of deer come by one evening and spend about 30 minutes making their way across from one side of the yard to the other. The outdoor grill was perfect for making dinner. And lunch. And breakfast. We didn't get a chance to use the hot tub, but like the house, it looked spotless. Overall, like I said, the house is beyond amazing. For skiers it's an absolute must (Windham mountain is minutes away, and so is Hunter mountain). For people looking for a quiet getaway, this place is perfect. Even if you just want to spend the night gazing at the star-filled sky (Milky Way is visible with the naked eye) while sitting in the hot tub, this is the place to go. Thank you again for allowing us to experience your property. It made our getaway even more spectacular by giving us such a wonderful place to start and end our days.
                                                              • Submitted: Sep 3, 2014
                                                              • Stayed: Aug 2014

                                                              Awesome house, Great location

                                                              5 of 5
                                                              I came here with a group of 9 for 2 nights/3 days. There was definitely not enough time to enjoy the area AND everything the house has to offer in such a short period of time! Nearby Kaaterskill falls is amazing and there are plenty of other hikes and lakes nearby. The house is in a wonderfully secluded area where everything is so quaint and pretty, but we probably could have stayed in the house all weekend and still have had a blast. The house is a perfect mixture of comfort and fun but still has a wonderfully rustic feel. We cooked all weekend and the kitchen was truly fully stocked. The fireplace, hot tub, and private lake were amazing! I'm just sad we didn't have enough time to enjoy the fire pit. Susan keeps everything well maintained and was a pleasure to deal with. I would definitely come back if I had the opportunity to do so!
                                                              • Submitted: Aug 29, 2014
                                                              • Stayed: Aug 2014

                                                              Nice home

                                                              5 of 5
                                                              We had a family get together in Windham and found this home to be a great location, just minutes from downtown and the ski resort. It was very clean and had all amenities that we needed. The owner Kip provided great customer service. He was easy to reach for any questions and was willing to meet any needs that we had.
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Aug 2014