Windham Vacation Rentals

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Vacation Rentals in Windham

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
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 ￥172,167
per night
Jun 2 - Jun 3
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
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.
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
Fridge, microwave, oven, stovetop
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
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Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Exterior
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
10.0 out of 10, Exceptional, (1)
"🙂"
The price is ￥33,804
per night
Jun 7 - Jun 8
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (199)
"Very clean, just as advertised. The stream behind the cottage is beautiful! Will stay there again if we get a chance to revisit the area. The host was extremely accommodating and available🙂"
The price is ￥26,641
per night
Jun 3 - Jun 4
Streamside Cottage Walking Distance to Town of Woodstock
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (153)
"We had a great time, and the space was great. The house is so spacious, and that was perfect for us. We would have liked a few more towels, a bit more soap and shampoo, and the grill didn't get hot enough to cook the steak we had brought. Overall a wonderful time. Thank you very much."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is ￥28,375
per night
Jun 2 - Jun 3
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (38)
"We spent the weekend and had a wonderful time. The property was conveniently located near the center of town while still being very quiet and private. The cottage is perfect for a couple’s weekend getaway. Great spot if you want to have a jumping off point to explore the area. Would definitely stay again."
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very Good, (37)
"Our trip was amazing. We do it again again and again"
The price is ￥19,654
per night
Jun 12 - Jun 13
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Starlite Motel
Exterior
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (229)
"Good for the price. "
The price is ￥19,654
per night
Jun 12 - Jun 13
Starlite Motel
Charming Artist's Retreat
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, (113)
"From beginning to end a pleasant stay. Owner was on contact to make sure everything was in order. Fresh cut flowers, plenty of clean white fluffy towels, comfortable bedding and the view through sparkling clear windows. What a wonderful way to spend the mother's day weekend with my daughter and spend some time outdoors exploring little Hudson river towns. 10 thumbs up!!!!"
Charming Artist's Retreat
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
Terrace/patio
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
10.0 out of 10, Exceptional, (7)
"House and location were great, would definitely come back."
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
Cozy Relaxing Retreat in Saugerties, NY
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (31)
"The house is secluded and peaceful with a huge deck for a cool breeze with morning coffee or an evening glass of wine. The house was spotless and well equipped with anything you could possibly need. Restaurants, grocery, and Katterskill Falls for hiking all within a 15-20 minute drive. Our host, Nick, was very attentive making sure everything was as we expected ( and it was). Would stay here again if the opportunity arises. I highly recommend this property for your vacation getaway."
Cozy Relaxing Retreat in Saugerties, NY
Updated Cabin on the Esopus
Property grounds
Updated Cabin on the Esopus
10.0 out of 10, Exceptional, (19)
"I had a really good experience with this cabin and the location. The owner lives on site, met me within two minutes of my arrival, and then gave me a brief and complete rundown of the property and the surrounding area highlights. Property sits on a beautiful stream and the large property is very well maintained. Inside of the cabin matches the photographs in the listing. A lot of outdoor activities near by. If you like hiking, there are really nice lakes and trailheads all along Route 214, which...
Updated Cabin on the Esopus
Beautiful House 0,5 Mile From Hunter Mountain
Exterior
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (189)
"it was all good"
Beautiful House 0,5 Mile From Hunter Mountain
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Outdoor spa tub
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, (163)
"The house was fantastic. Close to Hunter Mountain Ski Resort and a cute one street town. Peter and Lara had both wood burning stoves going for us when we arrived. The house is wonderful with a fun separate hang out place for the kids. Well equipped kitchen. Comfortable beds. Hot tub with wonderful views. All the firewood you could ever need. We will be back for sure!"
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
The Cabin at Chichester in the Catskills Mountains
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (165)
"Very clean, good area"
The Cabin at Chichester in the Catskills Mountains
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
9.6 out of 10, Exceptional, (42)
"We decided on a trip to Hunter Mountain with our family and some of my sons friends. I came across this house and let me tell you the pictures do not do it justice it’s even better in person!! We were beyond happy with the house and the location…. The house was fully stocked with everything you could imagine. So much room for our group of 13 including our golden retriever! The kids and adults loved the game room some adults even had a Pac-Man competition. We will definitely stay at this house...
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
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!!
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, (14)
"Clean and comfortable. We had a great time visiting with friends and family at my daughters baby shower!"
Charming Cottage in Private Lake Community (Pet-Friendly!)
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See all available properties in Windham
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 types of properties in Windham you may be interested in

Hotel Vienna
Exterior
Hotel Vienna
2.5 star property
9.2 out of 10, Wonderful, (359)
"Nice people and clean hotel"
The price is ￥21,256
per night
Jun 3 - Jun 4
Hotel Vienna
Eastwind Windham
Premium Suite | Desk, free WiFi, bed sheets
Eastwind Windham
2.0 star property
9.2 out of 10, Wonderful, (14)
"Interesting and different property but more expensive for drinks and dinner than I anticipated in such a quiet town. I enjoyed the communal dinner where we ate w other guests."
The price is ￥36,257
per night
Jun 2 - Jun 3
Eastwind Windham
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
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.

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Look no further and take a look at our great range of rental properties in Windham!

Frequently asked questions

Can I find vacation rentals in Windham?

Yes, we give you a choice of vacation rentals close to top points of interest in Windham, or you can select a more remote option if you'd like a relaxing place to stay. Discover why Windham is known for its ski slopes and mountain landscape. While you're here, grab a bite or have a drink at the coffeehouses.

What are some of the best vacation rentals in Windham?

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter: Visitors like this Windham vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travelers also rate SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball. as a favorite home for rent in Windham.

How many vacation rentals are there in Windham?

With 150 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What can I see and do in Windham?

While exploring the area, visit family-friendly sights like Zoom Flume, or get outside and enjoy nature at Ashland Park. Windham Country Club and Windham Mountain Resort are other places to visit while you're in town.

What are vacation rentals like in Windham?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Windham. Vacation rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.

Recent reviews of Windham properties
Expedia verified reviews

AutoCamp Catskills

AutoCamp Catskills

5/5 Excellent
"Super cute and cool experience! The staff are super friendly and helpful! Can’t wait to stay again! "
A verified traveler stayed at AutoCamp Catskills
Posted 19 hours ago
AutoCamp Catskills