Windham Vacation Rentals

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Aug 12 - Aug 13
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This weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Windham

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Property grounds

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.0 out of 10, Wonderful, (48)
"Great for in town stays"
The price is ￥16,626
￥29,767 total
includes taxes & fees
Aug 19 - Aug 20
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A'Neils Windham Ski Lodge & Family Retreat
Outdoor dining

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"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 ￥10,671
￥19,528 total
includes taxes & fees
Aug 17 - Aug 18
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 ￥19,448
￥37,811 total
includes taxes & fees
Aug 14 - Aug 15
Tiny House on Walnut Grove
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (55)
"Nice stays 👌 "
The price is ￥24,977
￥32,562 total
includes taxes & fees
Aug 27 - Aug 28
Postcard Cabins Eastern Catskills
Starlite Motel
Exterior

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (261)
"Quaint little place in the mountains, quiet. Beds were comfortable."
The price is ￥18,474
￥20,691 total
includes taxes & fees
Aug 18 - Aug 19
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, (43)
"Perfect place to reconnect with natural world and yourself"
The price is ￥18,474
￥24,001 total
includes taxes & fees
Sep 10 - Sep 11
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (247)
"A beautiful quiet setting! "
The price is ￥23,565
￥49,964 total
includes taxes & fees
Sep 2 - Sep 3
Streamside Cottage Half Mile to Town of Woodstock
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, (126)
"Great property for a ski trip to Belleayre. Close to the mountain. "
Stunning Catskills Cabin Getaway, facing BelleAyre
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!
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 ￥16,303
￥21,579 total
includes taxes & fees
Aug 18 - Aug 19
Sioux Tipi on Chloe's Lake
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.
Moonlight Reflections
Property grounds

Moonlight Reflections

10.0 out of 10, Exceptional, (94)
"Great stay! Very convenient to ski bellaeyre. "
Moonlight Reflections
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children's area

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is ￥26,678
￥46,479 total
includes taxes & fees
Aug 24 - Aug 25
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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 ￥20,275
￥40,399 total
includes taxes & fees
Aug 19 - Aug 20
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (71)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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
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, (90)
"This was exactly what we needed for a quick getaway after Christmas. Myra & Jerry were fantastic hosts, and the accommodations were cozy. We'd definitely come back. Thanks Myra & Jerry!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Mountain Chalet with Breathtaking Panoramic Views
Property grounds

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (173)
"Very pleasant stay close to markets, restaurant and ski resort. Lee was very responsive "
Mountain Chalet with Breathtaking Panoramic Views
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Great hotel"
Elena 1-night trip
Posted 1 day ago
Hotel Vienna

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?

A'Neils Windham Ski Lodge & Family Retreat: 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 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Windham?

With 149 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.