Holiday Rentals in Windham

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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, (143)
"A Big House has enough rooms and beds. Had mostly everything needed, and owner able to answer questions and solve problem in time. the backyard and forest would be better view in spring or summber. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

9.8 out of 10, Exceptional, (7)
"Our stay was really nice. The house was clean and had everything we needed. We loved being able to walk into town. "
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

10.0 out of 10, Exceptional, (3)
"We really appreciated that the property manager was easily reachable no matter the time of hour. The property was beautiful, clean, had free WI-FI and spacious. Because we arrived latter in the day, we also very much appreciated the complimentary snacks and coffee! "
The price is €393
includes taxes & fees
27 Nov - 28 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (244)
"Cosy room, clean bathroom, useable kitchen with all useful appliances. Loved the back yard with the fire pit. A little bit of a drive from our home but it was worth the effort. I would come again."
The price is €136
includes taxes & fees
5 Dec - 6 Dec
Starlite Motel

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is €143
includes taxes & fees
24 Nov - 25 Nov
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (224)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
The price is €315
includes taxes & fees
27 Nov - 28 Nov
Streamside Cottage Half Mile to Town of Woodstock

Cozy Relaxing Retreat in Saugerties, NY

10.0 out of 10, Exceptional, (42)
"Secluded house very quiet surrounding, owner was very quick to respond "
Cozy Relaxing Retreat in Saugerties, NY

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (175)
"This property is amazing and was exactly what I was looking for! We stayed two nights and upon arriving Paul greeted us and was very kind and helpful. The house was clean and everything was as described. We really enjoyed our stay and will come again."
The Cabin at Chichester in the Catskills Mountains

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (34)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (39)
"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"
The price is €274
includes taxes & fees
1 Dec - 2 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Cottage in Private Lake Community (Pet-Friendly!)

9.8 out of 10, Exceptional, (24)
"The White Bunny Cottage is a charming place. It is beautifully decorated and spotless! We enjoyed making dinner and using the tableware and baskets. Perfect for entertaining family. The country setting was perfect. Very quiet. Grocery and wine shop near by. Easy access to points of interest along the Hudson River. I would highly recommend the White Bunny Cottsge. "
Charming Cottage in Private Lake Community (Pet-Friendly!)

Beautiful, private Property/swimming pond

9.6 out of 10, Exceptional, (69)
"This home was perfect for our Labor Day weekend reunion, with everything we would need, easy use of fire pit, grill, deck and kitchen (but there is no dishwasher). Gisele was great to communicate with. Would definitely go again!"
Beautiful, private Property/swimming pond

Charming Artist's Retreat

9.8 out of 10, Exceptional, (129)
"Escaped Long Island’s noise, traffic and overall stress . Listened to owls, watched birds soaring, kicked up leaves and gazed at the periwinkle colored mountains while perched on a bench. Felt safe enough knowing civilization was near enough, would have liked a landline phone just in case of an emergency "
Charming Artist's Retreat

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

9.6 out of 10, Exceptional, (45)
"We really enjoyed our stay in Hunter. The house met our needs well for a large family gathering. The hot tub and game room were excellent. Beutiful inside.It is close to shopping and hiking trails in the area. We did a lot of cooking and could have used larger cutting boards and baking/roasting pans. Be aware that the house is right on the main road into Hunter. The pinball machine was frustrating at times because the ball would get stuck.Overall it was a great stay."
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

9.6 out of 10, Exceptional, (171)
"Everything was just perfect. The house was spacious and had so many wonderful amenities. Location was great, private and quiet. We enjoyed the hot tub under the stars each night to relax from the hiking! Highly recommend. "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

9.6 out of 10, Exceptional, (39)
"The house has anything you want . A private house nice town . Quite,"
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Bright Tucked-Away Cabin w/ Furnished Deck + Grill

9.0 out of 10, Wonderful, (25)
"Nice time visiting our children in college "
Bright Tucked-Away Cabin w/ Furnished Deck + Grill

7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim

10.0 out of 10, Exceptional, (212)
"We had a fantastic stay in Valentyna's home. We had a large group of 16 at the home during labor day weekend. We found the house large, clean, updated and had plenty of space. The bedrooms are roomy, the living spaces are even larger than pictured, and the five different outdoor areas are fantastic. The house has every amenity you can ask for. Direct lake access is steps from the house and the house is close to Hunter for the winter months. We had a great time and would happily stay again. "
The price is €727
includes taxes & fees
24 Nov - 25 Nov
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim

Moonlight Reflections

10.0 out of 10, Exceptional, (88)
"Very good for people on a short vacation."
Moonlight Reflections
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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Other types of properties in Windham you may be interested in

Hotel Vienna

2.5 star property
9.2 out of 10, Wonderful, (474)
"Pictures give a mOre grand impression that the reality"
Hotel Vienna

Wylder Hotel Windham

3.5 star property
8.8 out of 10, Excellent, (27)
"Beautiful property with great amenities! "
The price is €292
includes taxes & fees
24 Nov - 25 Nov
Wylder Hotel Windham

Eastwind Windham

2.0 star property
9.4 out of 10, Exceptional, (28)
"The Eastwinds in Wndham is a camping property with beautiful cabins that are very comfortable for campers and glampers! The staff is so accommodating and friendly. The property is magnificent. This was our second time here and cannot say enough great things about the Eastwinds, Staff, and the area of Windham. Very friendly town for a getaway or vacation."
The price is €226
includes taxes & fees
27 Nov - 28 Nov
Eastwind 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.

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. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travellers also rate Tuscan Year Round Beauty - Pickleball Court as a favourite home for rent in Windham.

How many holiday rentals are there in Windham?

With 140 Expedia holiday rentals, you're guaranteed to find just the right place for your Windham stay.

What can I see and do in Windham?

Catskill State Park and Ashland Park are a couple of lovely local spots to get outside and enjoy nature. 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.