Windham Holiday Rentals

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Holiday Rentals in Windham

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham
10.0 out of 10, Exceptional, (105)
"Rick has an incredible property to share and is a gracious host. A sure place to spend time with friends and family - cant wait to come back again."
United States
Chris R.
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

A'Neils Windham Ski Lodge & Family Retreat

Windham
9.8 out of 10, Exceptional, (31)
"Excellent! The host was super friendly, helpful and was an excellent communicator. We had a great time!"
United States
Ray L.
A'Neils Windham Ski Lodge & Family Retreat

Magical Home Located in Windham and Catskills

2.0 star property
Windham
10.0 out of 10, Exceptional, (12)
"Nice cozy home"
United States
Romonia F.
Magical Home Located in Windham and Catskills

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Windham
9.2 out of 10, Wonderful, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is AU$205
includes taxes & fees
30 Nov - 1 Dec
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Tiny House on Walnut Grove

2.0 star property
Ashland
4.0 out of 10, (2)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
The price is AU$401
includes taxes & fees
7 Dec - 8 Dec
Tiny House on Walnut Grove

Starlite Motel

2.5 star property
Big Indian
9.2 out of 10, Wonderful, (273)
"Awesome place to stay!"
United States
Earl
The price is AU$200
includes taxes & fees
11 Dec - 12 Dec
Starlite Motel

Streamside Cottage Half Mile to Town of Woodstock

Woodstock
10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
The price is AU$599
includes taxes & fees
13 Dec - 14 Dec
Streamside Cottage Half Mile to Town of Woodstock

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

Saugerties
8.2 out of 10, Very good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is AU$251
includes taxes & fees
10 Dec - 11 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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

Fleischmanns
9.6 out of 10, Exceptional, (63)
"Nice place. Enjoyed the hot tub. Good restaurant down the road. Just what we needed. "
United States
john C.
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

A Spectacular 50 Mile View of the Hudson Valley in all seasons

Saugerties
9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Stunning Catskills Cabin Getaway, facing BelleAyre

Fleischmanns
10.0 out of 10, Exceptional, (131)
"Absolutely fabulous place we stayed for my daughter’s wedding. "
United States
Robert Joseph J.
Stunning Catskills Cabin Getaway, facing BelleAyre

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
The price is AU$479
includes taxes & fees
28 Dec - 29 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville
10.0 out of 10, Exceptional, (123)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

A world where time stands still, close to Belleayre Ski & Wedding venues.

City Roxbury
9.4 out of 10, Exceptional, (30)
"Beautiful house, clean and in a beautiful location. A perfect home for rest and enjoyment in nature"
United States
Janko S.
The price is AU$1,223
includes taxes & fees
30 Dec - 31 Dec
A world where time stands still, close to Belleayre Ski & Wedding venues.

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

Hunter
10.0 out of 10, Exceptional, (271)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
United States
Sarah A.
The price is AU$1,450
includes taxes & fees
1 Dec - 2 Dec
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

West Kill
9.8 out of 10, Exceptional, (151)
"This is a fantastic place- lots of space and beautiful. Really enjoyed the hot tub"
United States
Evan S.
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

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

Hunter
9.6 out of 10, Exceptional, (51)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
United States
Chris S.
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

Mountain Top Retreat, 116 private acres

Hobart
9.6 out of 10, Exceptional, (98)
"Adorable cabin in a beautiful area. Perfect for a weekend getaway !!"
United States
Teresa M.
Mountain Top Retreat, 116 private acres

Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location

Lanesville
10.0 out of 10, Exceptional, (56)
"We had a wonderful stay at this very clean and cozy cabin! It was just the perfect summer getaway we were looking for. Mario and Giovanna were very welcoming and helpful with sharing activities to do during our stay. We enjoyed nearby hikes, campfires, cooking and just relaxing with our kids."
United States
Katy A.
Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths Sauna great location

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
The price is AU$225
includes taxes & fees
28 Dec - 29 Dec
Sioux Tipi on Chloe's Lake
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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Top Windham Hotel Reviews

Find out more about Windham

Everything you need to know about Windham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham holiday rentals we have selected for you start as low as AU$200 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts : This highly rated holiday home rental in Windham is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Our travellers also rate A'Neils Windham Ski Lodge & Family Retreat as a favourite home for rent in Windham.

How many holiday rentals are there in Windham?

With 149 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.