Windham Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 25 - Aug 26
Tomorrow
Aug 26 - Aug 27
This weekend
Aug 29 - Aug 31
Next weekend
Sep 5 - Sep 7

Vacation Rentals in Windham

A'Neils Windham Ski Lodge & Family Retreat
Outdoor dining

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (29)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat
Tuscan Year Round Beauty - Pickleball Court - Full Winter Rental Availability
Outdoor dining

Tuscan Year Round Beauty - Pickleball Court - Full Winter Rental Availability

10.0 out of 10, Exceptional, (104)
"A sublime weekend in a truly magical and beautiful estate. The al fresco dining and the nonstop outdoor activities will make for a memorable stay for any group!"
Tuscan Year Round Beauty - Pickleball Court - Full Winter Rental Availability
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

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

9.2 out of 10, Wonderful, (35)
"Great place for an incredible price. We would definitely stay here again."
The price is ￥9,257
￥17,932 total
includes taxes & fees
Aug 28 - Aug 29
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Tiny House on Walnut Grove
Terrace/patio

Tiny House on Walnut Grove

2.0 star property
4.0 out of 10, (1)
The price is ￥19,281
￥37,487 total
includes taxes & fees
Aug 27 - Aug 28
Tiny House on Walnut Grove
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (63)
"Really beautiful place to enjoy nature with family!!"
The price is ￥20,425
￥27,614 total
includes taxes & fees
Sep 1 - Sep 2
Postcard Cabins Eastern Catskills
Starlite Motel
Exterior

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (264)
"The property was beautiful! Definitely coming back!"
The price is ￥16,595
￥18,585 total
includes taxes & fees
Sep 25 - Sep 26
Starlite Motel
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

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

8.2 out of 10, Very Good, (46)
"Perfect place to reconnect with natural world and yourself"
The price is ￥18,368
￥23,864 total
includes taxes & fees
Sep 3 - Sep 4
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
Terrace/patio

Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

9.8 out of 10, Exceptional, (79)
"Location is great; close to a lot of hiking opportunities and right in the middle of breathtaking scenery. The house was clean and provided excellent accomodations."
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Exterior

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

9.8 out of 10, Exceptional, (91)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Exterior

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (27)
"Great location "
The price is ￥23,143
￥49,751 total
includes taxes & fees
Aug 28 - Aug 29
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children's area

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is ￥26,449
￥45,257 total
includes taxes & fees
Sep 7 - Sep 8
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals
Dining

PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals

8.4 out of 10, Very Good, (61)
"The home was nice and cozy. The owner was soo nice and soo responsive. Great place fo rent. "
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Exterior

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

9.6 out of 10, Exceptional, (53)
"Great location, Great Hot Tub, Great Catskills Mountains "
The price is ￥18,382
￥37,998 total
includes taxes & fees
Sep 1 - Sep 2
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Jessie's Harvest House
Bar (on property)

Jessie's Harvest House

10.0 out of 10, Exceptional, (1)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
The price is ￥15,870
￥27,978 total
includes taxes & fees
Aug 27 - Aug 28
Jessie's Harvest House
Sioux Tipi on Chloe's Lake
Exterior

Sioux Tipi on Chloe's Lake

9.6 out of 10, Exceptional, (5)
"This was such a cool experience Id love to go back! "
The price is ￥16,163
￥21,394 total
includes taxes & fees
Sep 7 - Sep 8
Sioux Tipi on Chloe's Lake
Stunning Catskills Cabin Getaway, facing BelleAyre
Smart TV, fireplace, table tennis, video library

Stunning Catskills Cabin Getaway, facing BelleAyre

9.8 out of 10, Exceptional, (127)
"Great property for a ski trip to Belleayre. Close to the mountain. "
Stunning Catskills Cabin Getaway, facing BelleAyre
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (249)
"A beautiful quiet setting! "
The price is ￥21,894
￥47,561 total
includes taxes & fees
Sep 2 - Sep 3
Streamside Cottage Half Mile to Town of Woodstock
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Fridge, microwave, oven, stovetop

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
Fridge, microwave, oven, stovetop

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.8 out of 10, Exceptional, (46)
"The perfect family getaway"
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
Suites on Main
Studio Suite | Private kitchen | Fridge, microwave, stovetop, coffee/tea maker

Suites on Main

3.0 star property
7.2 out of 10, Good, (78)
"Good place to stay and reasonable "
The price is ￥16,016
￥23,201 total
includes taxes & fees
Sep 2 - Sep 3
Suites on Main
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Find out more about Windham

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
  • Use the map to find apartments and other holiday homes in the Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

Look no further and take a look at our great range of rental properties in Windham!

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?

Tuscan Year Round Beauty - Pickleball Court - Full Winter Rental Availability: Visitors like this Windham vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Our travelers also rate A'Neils Windham Ski Lodge & Family Retreat as a favorite home for rent in Windham.

How many vacation rentals are there in Windham?

With 151 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.