Windham Holiday Rentals

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Check prices for these dates

Tonight
17 Aug - 18 Aug
Tomorrow
18 Aug - 19 Aug
Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug

Holiday 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
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 HK$880
HK$1,576 total
includes taxes & fees
18 Aug - 19 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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 HK$563
HK$1,031 total
includes taxes & fees
18 Aug - 19 Aug
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (57)
"Really beautiful place to enjoy nature with family!!"
The price is HK$1,322
HK$1,724 total
includes taxes & fees
18 Aug - 19 Aug
Postcard Cabins Eastern Catskills
Starlite Motel
Exterior

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (262)
"Quaint little place in the mountains, quiet. Beds were comfortable."
The price is HK$978
HK$1,095 total
includes taxes & fees
18 Aug - 19 Aug
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 HK$978
HK$1,271 total
includes taxes & fees
3 Sept - 4 Sept
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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 HK$861
HK$1,139 total
includes taxes & fees
24 Aug - 25 Aug
Sioux Tipi on Chloe's Lake
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Fridge, microwave, oven, stovetop

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

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! 3rd night 1/2 price w/weekend
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (248)
"A beautiful quiet setting! "
The price is HK$1,244
HK$2,638 total
includes taxes & fees
2 Sept - 3 Sept
Streamside Cottage Half Mile to Town of Woodstock
Stunning Catskills Cabin Getaway, facing BelleAyre
Smart TV, fireplace, ping pong, 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
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.
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 HK$1,176
HK$2,580 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Private kitchen

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

7.4 out of 10, Good, (3)
"Place was as described. Small 1 bedroom apartment right in downtown Woodstock. Great location. Space was perfect for my daughter and I. Loved the decorations."
The price is HK$1,225
HK$2,871 total
includes taxes & fees
27 Aug - 28 Aug
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
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 HK$1,408
HK$2,410 total
includes taxes & fees
7 Sept - 8 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Private Yacht on Catskill Creek
Property grounds

Private Yacht on Catskill Creek

9.6 out of 10, Exceptional, (24)
"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."
The price is HK$1,162
HK$1,922 total
includes taxes & fees
19 Aug - 20 Aug
Private Yacht on Catskill Creek
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
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
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

Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

10/10 Excellent
"Kaatskill Mountain Club is a wonderful hotel. The pool is lovely and the amenities and the staff are great. There are two things I would suggest that would make the customer’s stay more comfortable. The first one is providing a mini refrigerator in the studio units. That would be most helpful. Secondly is installing at least one handle bar in the shower stall for customers who have balance/mobility issues. That said I have recommended this facility to my family and friends. Those who have stayed have loved it. I will be returning. "
Lydia 5-night trip
Posted 1 day ago
Kaatskill Mountain Club at Hunter Mountain

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?

A'Neils Windham Ski Lodge & Family Retreat: 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 10 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.

How many holiday rentals are there in Windham?

With 151 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.