Windham Vacation Rentals

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Vacation Rentals in Windham

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, 131 reviews
"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 CA $1,497
CA $2,376 total
includes taxes & fees
Jun 11 - Jun 12
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, 86 reviews
"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.
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!
10.0 out of 10, Exceptional, 1 review
"🙂"
The price is CA $296
CA $376 total
includes taxes & fees
Jun 21 - Jun 22
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, 229 reviews
"Good for the price. "
The price is CA $171
CA $191 total
includes taxes & fees
Jun 11 - Jun 12
Starlite Motel
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, 199 reviews
"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 CA $258
CA $491 total
includes taxes & fees
Jun 17 - Jun 18
Streamside Cottage Walking Distance to Town of Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, 32 reviews
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is CA $246
CA $383 total
includes taxes & fees
Jun 16 - Jun 17
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, 163 reviews
"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!
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, 38 reviews
"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
8.4 out of 10, Very good, 37 reviews
"Our trip was amazing. We do it again again and again"
The price is CA $171
CA $198 total
includes taxes & fees
Jun 16 - Jun 17
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Charming Artist's Retreat
10.0 out of 10, Exceptional, 114 reviews
"This is our second time staying at the cottage. What beautiful weather in such a beautiful setting. Incredible motorcycle ride through the mountains. Thank you Maureen. Robin & Bruce"
Charming Artist's Retreat
Mountain Chalet with Breathtaking Panoramic Views
9.8 out of 10, Exceptional, 144 reviews
"It’s all about the view. Quiet, compact little chalet, a short drive to everything Catskills. We always come back."
Mountain Chalet with Breathtaking Panoramic Views
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
8.6 out of 10, Excellent, 14 reviews
"There were 26 of us for a nice family gathering. Plenty of bedrooms and beds. Only 2 showers for 26 people a little challenging. Kitchen facilities lacking materials as noted in the listing. Bring your own pots and pans. Hot tub and fire pit were a nice addition. All in all, worked out great."
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
Your peaceful, private retreat to get away with friends & family!
10.0 out of 10, Exceptional, 23 reviews
"Wonderful location and fabulous amenities."
Your peaceful, private retreat to get away with friends & family!
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, 153 reviews
"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!
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, 31 reviews
"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
10.0 out of 10, Exceptional, 19 reviews
"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
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, 10 reviews
"The number of bedrooms and bathrooms was great for the 13 of us. The big kitchen, pantry and long dining tables made for fun interaction. The game room with pool table and ping pong table were perfect for after dinner fun. Beautiful property on the river. We plan to go back. Historic homes are tough to maintain and our hope is that it is as nice in the future as it was this week."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, 27 reviews
"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
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, 14 reviews
"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.

Windham Vacation Rental Travel Info

Number of vacation rentals
51
Popular accommodation
Windham private vacation homes
Known landmarks
Hunter Mountain, Zoom Flume and Mountain Top Arboretum
International airports
Albany, NY (ALB-Albany Intl.) and Hudson, NY (HCC-Columbia County)

Other types of properties in Windham you may be interested in

Hotel Vienna
2.5 star property
9.2 out of 10, Wonderful, 362 reviews
"Our stay was great, everything was clean and quiet. The staff was friendly and very accommodating for our dog. He also loved his stay! "
The price is CA $217
CA $235 total
includes taxes & fees
Jun 16 - Jun 17
Hotel Vienna
Eastwind Windham
2.0 star property
8.8 out of 10, Excellent, 16 reviews
"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 CA $289
CA $322 total
includes taxes & fees
Jun 16 - Jun 17
Eastwind Windham
Winwood Inn & Condominiums
3.0 star property
8.6 out of 10, Excellent, 271 reviews
"It was an amazing stay for our ski trip. Very clean and comfortable beds. Convenient with a good quality food market next door. Kids love the game room as an after ski activity. Only wish the kitchen was equipped with dishwasher and stocked with cooking oil."
The price is CA $198
CA $214 total
includes taxes & fees
Jun 16 - Jun 17
Winwood Inn & Condominiums
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 152 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