Windham Holiday Rentals

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Holiday Rentals in Windham

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is AU$2,553
per night
6 May - 7 May
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Exterior
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
10.0 out of 10, Exceptional, (1)
"🙂"
The price is AU$384
per night
6 May - 7 May
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
Fridge, microwave, oven, stovetop
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
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Hotel Woodstock - Iris suite
1 bedroom, Internet, bed sheets
Hotel Woodstock - Iris suite
9.6 out of 10, Exceptional, (45)
"Cool propertry in a unique town"
The price is AU$341
per night
9 May - 10 May
Hotel Woodstock - Iris suite
The Cabin at Chichester in the Catskills Mountains
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (163)
"Came up to the area for live music. I had my daughter meet me there for the weekend so we can have peaceful quality time together. We accomplished that with this stay. We found our way to the river and spend most of our time chilling and catching up there. Bring bug spray! The cottage was just enough for our needs. We would recommend this retreat to anyone looking to unplug and regroup. We ourselves would stay again for sure!"
The Cabin at Chichester in the Catskills Mountains
Starlite Motel
Exterior
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (228)
"Property was clean. Amenities were as advertised. However, shower temperatures fluctuate from hot to freezing. Stovetop was uneven, making it somewhat difficult to cook. "
The price is AU$213
per night
6 May - 7 May
Starlite Motel
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (37)
"Our trip was amazing. We do it again again and again"
The price is AU$225
per night
5 May - 6 May
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (194)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is AU$504
per night
13 May - 14 May
Streamside Cottage Walking Distance to Town of Woodstock
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, (37)
"A perfect location and the cottage was set up with great attention to detail. Everything was very clean and comfortable. The property is beautiful too. John and Mollie are very responsive hosts and provided us with anything we needed. Could not ask for more. Highly recommend!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
Aerial view
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
9.8 out of 10, Exceptional, (66)
"We just needed a place to relax and recharge for a few days and this house was perfect for us and our teenage son, who enjoyed skiing at Hunter and exploring the grounds with our dog. The house had everything we needed."
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Pool
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
8.8 out of 10, Excellent, (5)
"Stay, house, check in were all great. It was pretty far to Hunter mountain but the house was perfect for our little getaway!"
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
1 bedroom, iron/ironing board, free WiFi, bed sheets
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
10.0 out of 10, Exceptional, (7)
"Beautiful loft with amazIng views and an adorable town near by. Loved this place."
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
Catskills Windham Hunter Mountain Cabin Getaway
Exterior
Catskills Windham Hunter Mountain Cabin Getaway
9.2 out of 10, Wonderful, (17)
"Nice layout and Spacious home. Was warm and plenty of room for all families. We had a great time. Hot tub was cleaned when we arrived."
The price is AU$927
per night
5 May - 6 May
Catskills Windham Hunter Mountain Cabin Getaway
Cozy Relaxing Retreat in Saugerties, NY
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (29)
"The accommodations were excellent. We were a couple, but the house would be great for two couples. We loved the setting! The host has thought of everything, and the place is equipped to the max. Just bring yourself! Perfect location to explore the area."
Cozy Relaxing Retreat in Saugerties, NY
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Outdoor spa tub
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, (163)
"The house was fantastic. Close to Hunter Mountain Ski Resort and a cute one street town. Peter and Lara had both wood burning stoves going for us when we arrived. The house is wonderful with a fun separate hang out place for the kids. Well equipped kitchen. Comfortable beds. Hot tub with wonderful views. All the firewood you could ever need. We will be back for sure!"
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"Beautiful private property. House is huge, plenty of space for our gang to spread out and get some privacy if needed. Comfortable living room with window views of nature. Great communication home owner. We will definitely be back!"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Romantic Luxury Chalet With Private Pool
1 bedroom, free WiFi, bed sheets
Romantic Luxury Chalet With Private Pool
10.0 out of 10, Exceptional, (259)
"Richard was very kind and thoughtful. The stay was very comfortable and Richard provided many ideas for things to in the vicinity. We will definitely consider staying here again if we're back in the area."
Romantic Luxury Chalet With Private Pool
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
Property grounds
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
10.0 out of 10, Exceptional, (208)
"House came with great amenities and host was very communicative and flexible"
The price is AU$1,230
per night
7 May - 8 May
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (31)
"Beautiful nature at the foot of a quiet retreat cottage, a mile away from the Woodstock strip and Comeau park and 4 miles from the Ashoka rail trail was an ideal access to peace and fun. I would definitely return and I appreciated the owners flexibility, great communication, and allowance for pets."
The price is AU$434
per night
5 May - 6 May
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Don't see what you're looking for?
See all available properties in Windham
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.

Windham Holiday Home Travel Info

Number of holiday homes
51
Popular accommodation
Windham private holiday homes
Known landmarks
Hunter Mountain, Zoom Flume and Mountain Top Arboretum
International airports
Albany, NY (ALB-Albany Intl.) and Hudson, NY (HCC-Columbia County)

Other types of properties in Windham you may be interested in

Hotel Vienna
Exterior
Hotel Vienna
2.5 star property
9.2 out of 10, Wonderful, (352)
"Solid not spectacular. Staff was great"
The price is AU$230
per night
21 May - 22 May
Hotel Vienna
Winwood Inn & Condominiums
Dining
Winwood Inn & Condominiums
3.0 star property
8.6 out of 10, Excellent, (270)
"It was an amazing stay for our ski trip. Very clean and comfortable beds. Convenient with a good quality food market next door. Kids love the game room as an after ski activity. Only wish the kitchen was equipped with dishwasher and stocked with cooking oil."
The price is AU$230
per night
5 May - 6 May
Winwood Inn & Condominiums
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is AU$2,553
per night
6 May - 7 May
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
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.

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$213 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?

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter: This highly rated holiday home rental in Windham is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Windham?

With 155 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.

Recent reviews of Windham properties
Expedia verified reviews

Shandaken Inn

Shandaken Inn

5/5 Excellent
"Very friendly staff, including Miranda as our “Emotional Support Concierge,” all of you were very welcoming and helpful. I would definitely recommend your inn to anyone. Food was delicious and ample, wait staff very helpful. All in all, had a great time. "
A verified traveller stayed at Shandaken Inn
Posted 1 day ago
Shandaken Inn