Windham Holiday Rentals

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Check prices for these dates

Tonight
1 Jul - 2 Jul
Tomorrow
2 Jul - 3 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

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, (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
Magical Home Located in Windham and Catskills
Property grounds

Magical Home Located in Windham and Catskills

2.0 star property
10.0 out of 10, Exceptional, (9)
"Nice cozy home"
Magical Home Located in Windham and Catskills
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 communication with host Nice spacious clean apartment. Good location "
The price is HK$918
HK$1,619 total
includes taxes & fees
2 Jul - 3 Jul
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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 HK$954
HK$1,903 total
includes taxes & fees
6 Jul - 7 Jul
Tiny House on Walnut Grove
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Exterior

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

The price is HK$1,915
HK$3,578 total
includes taxes & fees
7 Jul - 8 Jul
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.0 out of 10, Wonderful, (25)
"Perfect place to stay during a house hunt in the area. Great for pups too!"
The price is HK$1,405
HK$1,814 total
includes taxes & fees
6 Jul - 7 Jul
Postcard Cabins Eastern Catskills
Starlite Motel
Exterior

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (256)
"Quaint little place in the mountains, quiet. Beds were comfortable."
The price is HK$936
HK$1,048 total
includes taxes & fees
7 Jul - 8 Jul
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, (42)
"Perfect place to reconnect with natural world and yourself"
The price is HK$981
HK$1,275 total
includes taxes & fees
2 Jul - 3 Jul
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Terrace/patio

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$1,413
HK$2,409 total
includes taxes & fees
13 Jul - 14 Jul
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Moonlight Reflections
Property grounds

Moonlight Reflections

10.0 out of 10, Exceptional, (92)
"Great stay! Very convenient to ski bellaeyre. "
Moonlight Reflections
Mountain Chalet with Breathtaking Panoramic Views
Property grounds

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (170)
"Very pleasant stay close to markets, restaurant and ski resort. Lee was very responsive "
Mountain Chalet with Breathtaking Panoramic Views
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
3 bedrooms, iron/ironing board, WiFi, bed sheets

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (175)
"Really enjoyed our stay for a family reunion."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
A-Frame of Mind
Exterior

A-Frame of Mind

10.0 out of 10, Exceptional, (57)
"Great place, great host. {ictures dont do it justice"
A-Frame of Mind
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, (87)
"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
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$863
HK$1,143 total
includes taxes & fees
6 Jul - 7 Jul
Sioux Tipi on Chloe's Lake
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, (64)
"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
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (240)
"The house was just as advertised. It is cozy and clean, on a gorgeous stream, and close to town. We'll definitely be back!"
Streamside Cottage Half Mile to Town of Woodstock
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Interior

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (15)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Outdoor dining

Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

9.6 out of 10, Exceptional, (179)
"Would certainly stay here again and highly recommend it for a private retreat in the woods, yet so close to town! Wonderful location for my dog to come too! We all enjoyed the hot tub and my sons loved keeping the wood stove full. Beds were comfortable and clean. Hosts were very friendly and welcoming. "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
Fridge, microwave, oven, stovetop

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (42)
"The perfect family getaway"
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
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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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?

Magical Home Located in Windham and Catskills: This highly rated holiday home rental in Windham offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 147 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.