Windham Holiday Rentals

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Holiday Rentals in Windham

Tuscan Year Round Beauty - Pickleball Court

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

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (146)
"Thank you!! We had a wonderful ski weekend. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

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

9.8 out of 10, Exceptional, (9)
"We had the best time! The property was perfect! Plenty of bedrooms and bathrooms plus gathering spaces galore ! The kitchen was stocked with all the necessities. We had 6 children age 8 and under so the outside property was perfect. Just enough snow for a snowman and some sledding! Plus an enormous deck and wrap around porch. There was a laundry and plenty of towels , pillows and cozy blankets! We will definitely be back! "
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, (4)
"Great place to stay very accommodating more than expected "
The price is AU$835
includes taxes & fees
28 Jan - 29 Jan
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (247)
"Cozy,excellent cable package…"
The price is AU$229
includes taxes & fees
27 Jan - 28 Jan
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 AU$236
includes taxes & fees
29 Jan - 30 Jan
'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, (226)
"Very comfortable place with a view of a stream right outside the window. Close to Woodstock stores. "
Streamside Cottage Half Mile to Town of Woodstock

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (178)
"The cabin was great, really fun environment, host really kept the place nice and clean. I would definitely suggest watch horror late night with all the lights off. You will have a great experience if you enjoy a little spooky night. :)"
The Cabin at Chichester in the Catskills Mountains

A-Frame of Mind

10.0 out of 10, Exceptional, (45)
"My daughter and I thoroughly enjoyed our stay at Nick’s house. The house was spotlessly clean and fully equipped. It was great to be able to relax after the Christmas rush. We look forward to visiting the house again."
A-Frame of Mind

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (40)
"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 AU$455
includes taxes & fees
2 Feb - 3 Feb
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!

9.8 out of 10, Exceptional, (72)
"This entire place is amazing! I would definitely go back. "
Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!

Charming Artist's Retreat

10.0 out of 10, Exceptional, (133)
"This super cozy cabin is perfectly located and close to major Catskills towns. Yet, Maureen has done an amazing job at creating a space that feels far away from every thing. Town and groceries are less than 10mins away. We visited Kingston and Woodstock - also nearby. The nearby trail options are endless too.This home is exemplar of what VRBO stands for. Thank you, Maureen! "
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

Moonlight Reflections

10.0 out of 10, Exceptional, (91)
"Great stay! Very convenient to ski bellaeyre. "
Moonlight Reflections

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (125)
"We had a fantastic time staying at this house. It’s very close to the skiing area. The dining area is big enough to fit a big group of people like us. The hot tub is a plus in this cold weather. The gaming area is pretty roomy. We will plan to come back in the future. Thank you! "
Beautiful new house 3/4 mile from Hunter Mountain

Catskills Windham Hunter Mountain Cabin Getaway

9.0 out of 10, Wonderful, (25)
"Quiet stay in the mountains in the summer."
The price is AU$1,182
includes taxes & fees
29 Jan - 30 Jan
Catskills Windham Hunter Mountain Cabin Getaway

Beautiful House 0,5 Mile From Hunter Mountain

9.8 out of 10, Exceptional, (196)
"Very accommodating host! Thanks for the stay. Definitely consider staying again! Lovely layout, airy, roomy. Host generous with paper goods etc. Thanks for a great vacation!"
Beautiful House 0,5 Mile From Hunter Mountain

7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. 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 AU$1,334
includes taxes & fees
20 Jan - 21 Jan
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

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
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, (503)
"Really nicely updated, loved the sauna, and the nice breakfast bar options! Beautiful view from our balcony, would return again!"
The price is AU$320
includes taxes & fees
28 Jan - 29 Jan
Hotel Vienna

Wylder Hotel Windham

3.5 star property
8.6 out of 10, Excellent, (35)
"No coffee in the room. No “normal” TV. Only streaming which is a bummer. "
The price is AU$383
includes taxes & fees
27 Jan - 28 Jan
Wylder Hotel Windham

Eastwind Windham

2.0 star property
9.4 out of 10, Exceptional, (37)
"Excellent except we were on the first floor and there was no soundproofing between floors. We could hear every step in room above. And music and talking from the lounge until 11pm. After that it was perfectly quiet. The bartender Jamie was wonderful as was the communal dinner. Highly recommend!"
The price is AU$396
includes taxes & fees
20 Jan - 21 Jan
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, Ski Lodge: 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 148 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.