Windham Holiday Rentals

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Holiday 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 NZ$2,856
includes taxes & fees
1 Jun - 2 Jun
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 NZ$446
includes taxes & fees
7 Jun - 8 Jun
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
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 NZ$544
includes taxes & fees
3 Jun - 4 Jun
Streamside Cottage Walking Distance to Town of Woodstock
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!
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 NZ$458
includes taxes & fees
16 Jun - 17 Jun
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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 NZ$237
includes taxes & fees
5 Jun - 6 Jun
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, 229 reviews
"Good for the price. "
The price is NZ$229
includes taxes & fees
4 Jun - 5 Jun
Starlite Motel
Charming Artist's Retreat
10.0 out of 10, Exceptional, 113 reviews
"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!
10.0 out of 10, Exceptional, 7 reviews
"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
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
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, 189 reviews
"it was all good"
Beautiful House 0,5 Mile From Hunter Mountain
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!
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, 165 reviews
"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
9.6 out of 10, Exceptional, 42 reviews
"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!!
9.8 out of 10, Exceptional, 67 reviews
"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!)
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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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
2.5 star property
9.2 out of 10, Wonderful, 359 reviews
"Nice people and clean hotel"
The price is NZ$281
includes taxes & fees
10 Jun - 11 Jun
Hotel Vienna
Eastwind Windham
2.0 star property
9.2 out of 10, Wonderful, 14 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 NZ$419
includes taxes & fees
2 Jun - 3 Jun
Eastwind Windham
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.
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windham holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windham. 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 Windham. 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 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 holiday 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 Windham short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing 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 coffee shops.

What are some of the best holiday rentals that Windham has to offer?

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter: This highly rated holiday home rental in Windham is located on a river, and has a fireplace, a patio and a BBQ 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 travellers also rate SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball. as a favourite home for rent in Windham.

How many holiday rentals are there in Windham?

With 150 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.

Recent reviews of Windham properties
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