Search Vacation Homes in Windham

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Compare Vacation Homes in Windham with updated reviews, rates, and availability.

Interior
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Property grounds
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
10.0 out of 10, Exceptional, (105)
"Great location. Comfortable space. The only drawback was the downstairs bedroom mattress."
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
Fridge, microwave, oven, stovetop
Catskills Getaway: 3BR, Pool, Hot Tub, Firepit, Ping-Pong, minutes from Hudson
10.0 out of 10, Exceptional, (1)
"This place is such a great value—beautiful, private, well thought out. Upon entering the cozy home, we were greeted with warmth and comfort. House has everything you need to make you feel at home. One of the highlights of our stay was the well-equipped kitchen. We prepared delicious meals and enjoyed our creations in the charming dining area. I recommend this house to anyone seeking a cozy getaway with friends and family."
Catskills Getaway: 3BR, Pool, Hot Tub, Firepit, Ping-Pong, minutes from Hudson
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Fridge, microwave, oven, stovetop
FOUR SEASON Catskills Home - Secluded & Spacious w/ Secret Waterfall
10.0 out of 10, Exceptional, (29)
"Wonderful very large home in the mountains. Quiet and peaceful. Enjoyed our Thanksgiving holiday here with plenty of room for cooking and lounging. Able to bring our dog too which was an added plus. Small village nearby with cute shops for Saturday shopping and grocery store within 5 miles. House has everything you need."
FOUR SEASON Catskills Home - Secluded & Spacious w/ Secret Waterfall
Exterior
Cozy Country Farmhouse Along the Catskill Scenic Trail
10.0 out of 10, Exceptional, (104)
"We had the best time! The house was clean with comfy beds, it had all the basic supplies we needed, and had a few fun games to play and interesting books to read during the evenings. The views were beautiful and we enjoyed exploring/walking on the property. The house was close to the bookstores in Hobart as well as delicious local restaurants. The Rich Farm farmhouse was a great place to stay. 😊"
The price is ¥27,262
¥49,616 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Country Farmhouse Along the Catskill Scenic Trail
Property grounds
Catskill Vacation Rental: Private Deck & Fire Pit
10.0 out of 10, Exceptional, (2)
"This is a great place. The interior furnishings are welcoming and a cool retro style. The household goods are top notch. Super convenient for groceries, drug stores, restaurants. An easy hop to Albany. The fire pit is a nice place to relax. We'll return!"
Catskill Vacation Rental: Private Deck & Fire Pit
Living area | TV, fireplace, DVD player, books
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
10.0 out of 10, Exceptional, (82)
"Great country house, well situated near town, with stream in the rear. Would definitely stay here agin. Excellent communication with the owner, whose attention to detail helps to make this a comfortable stay. Well equipped kitchen -- pretty much everything you might need. This is a cozy house, not a fancy house. Very comfortable for a family. Stairs are a bit steep for little kids with kids beds upstairs."
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
Exterior
Last minute deal!! Scandinavian BBQ hut and Hot tub
10.0 out of 10, Exceptional, (55)
"My family and I stayed here for an early spring getaway with our dog. The property is very cute and perfect for a family. The pizza oven was a fun addition and made for a nice evening with delicious food. The hot tub is also very nice. The house is not far from access to several walks and hikes."
Last minute deal!! Scandinavian BBQ hut and Hot tub
Property grounds
The 212 Escape - Main House
10.0 out of 10, Exceptional, (1)
"This stunning, sun-drenched property had ample space for all of our guests and unique amenities (yoga room, sauna, etc.) that made it stand out from other rentals. Each of the bedrooms are well-sized and beautifully decorated."
The 212 Escape - Main House
Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is ¥170,579
¥277,911 total
includes taxes & fees
May 28 - May 29
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Property grounds
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
10.0 out of 10, Exceptional, (208)
"House came with great amenities and host was very communicative and flexible"
The price is ¥50,629
¥109,358 total
includes taxes & fees
May 15 - May 16
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
Fridge, microwave, stovetop, dishwasher
Tannersville Retreat w/ Pool, 6 Mi to Hunter Mtn!
10.0 out of 10, Exceptional, (48)
"Loved the house and it was perfect for our old friends hiking weekend"
Tannersville Retreat w/ Pool, 6 Mi to Hunter Mtn!
Fridge, microwave, oven, stovetop
Your peaceful, private retreat to get away with friends & family!
10.0 out of 10, Exceptional, (22)
"The place and host were amazing. The property was well kept and well appointed for our stay. It is nicely secluded, and the hot tub was perfect for relaxing."
Your peaceful, private retreat to get away with friends & family!
Property grounds
Birch Creek Retreat ~ Rustic & Secluded ~ 8br, 8ba 3min Lake+Ski, NEW SAUNA!
10.0 out of 10, Exceptional, (82)
"This was a return winter visit for our family. We love this property with its walking trails and other outside amenities. Plus the house is large enough for our family of ten to not get in each others hair. The kitchen is great and well stocked with glasses, dishes, pots and pans as we cook dinner as a family every night. We explored some towns this time and enjoyed the area. And of course, I need to include, that gem of a ski mountain, Belleayre. just down the street.. Other than wanting more...
Birch Creek Retreat ~ Rustic & Secluded ~ 8br, 8ba 3min Lake+Ski, NEW SAUNA!
2 bedrooms, desk, iron/ironing board, WiFi
Private Cabin by River with Fireplace | By Summer
10.0 out of 10, Exceptional, (4)
"Location of property was great. Home was very clean, kitchen well stocked, nice bathrooms, comfortable beds and nice towels. Great for 2-4 people. Didn’t have a lot of luck with places to eat; however, we were there on a Sunday to Wednesday so some restaurants are closed on Mondays and Tuesdays. Extra pluses were a welcoming bottle of wine and a bag of local coffee. Small negatives were the on/ off of the heater is very loud and occasionally there is an unpleasant odor in the home??"
The price is ¥35,051
¥94,465 total
includes taxes & fees
May 17 - May 18
Private Cabin by River with Fireplace | By Summer
Aerial view
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
9.8 out of 10, Exceptional, (67)
"We travel to the Catskills at least once a year and stay at various locations. What sets this property apart is the true seclusion and absolutely no distractions from the nature around you. Even though it is close to hubs like Wyndham and Hunter (less than 20 to both) when sitting outside it feels like you are in the middle of nowhere. Inside is clean, cosey by the fire, and lots of fun things to do with our teenagers. Definitely would stay again."
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
2 bedrooms, free WiFi, bed sheets
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
9.8 out of 10, Exceptional, (19)
"Amazing house very clean very warm a place to be for a weekend highly recommend The owner is very helpful for everything for check in check out and every question that you have"
The price is ¥30,377
¥61,072 total
includes taxes & fees
May 15 - May 16
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Property grounds
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
9.8 out of 10, Exceptional, (80)
"Natalya was a great host! Property was very nice and great location to Hunter!"
The price is ¥62,312
¥105,930 total
includes taxes & fees
May 15 - May 16
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Interior
Private Contemporary Cottage with heated pool, hot tub and wide mountain views.
9.8 out of 10, Exceptional, (70)
"Beautiful well appointed home. Great for large groups. The kitchen is well stocked with everything to cook and serve meals. The beds were comfortable. Gorgeous views and the hot tub on a chilly November night was amazing."
Private Contemporary Cottage with heated pool, hot tub and wide mountain views.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Windham

Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is ¥170,579
¥277,911 total
includes taxes & fees
May 28 - May 29
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Exterior
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
10.0 out of 10, Exceptional, (1)
"🙂"
The price is ¥31,000
¥39,724 total
includes taxes & fees
Jun 5 - Jun 6
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Outdoor dining
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, (86)
"Stayed here with a group of friends, and loved it! We had terrible weather, but the house was the best place to be stuck inside. We made pizzas in the outdoor oven, and enjoyed the hot tub. Can't recommend enough! The property manager Alan was awesome."
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.