Windham holiday rentals

We found 802 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Windham by choosing from 141 houses, 32 flats and other holiday rentals. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include air conditioning and a pool. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Windham

Showing deals for:18 Dec - 25 Dec

Sunroom
Hot tub
Fully finished attic: full size bed
Kitchen
Exceptional
(90 reviews)

Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!

Tannersville

12% off
AU$16,176
for 7 nights, 1 home
AU$2,311 per night
includes taxes & fees
Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!
Outdoor dining
Exterior
Living area
Private kitchen
Exceptional
(7 reviews)

Modern Mountain View Chalet in Windham

Windham

8% off
AU$8,084
for 7 nights, 1 chalet
AU$1,155 per night
includes taxes & fees
Modern Mountain View Chalet in Windham
Exterior
Counter island- wraps around range with seating for 10
Indoor 8 person 12 x 12 Spa with access to deck & pool via sliding door.
Property grounds
Exceptional
(172 reviews)

Streamside - Hunter Mtn Ski Windham Luxury Home

Prattsville

8% off
AU$12,365
for 7 nights, 1 home
AU$1,766 per night
includes taxes & fees
Streamside - Hunter Mtn Ski Windham Luxury Home
Living area
Interior
Terrace/patio
Living area
Exceptional
(20 reviews)

Woodside Cabin #2 on Lake Heloise

Windham

17% off
AU$2,199
for 7 nights, 1 cabin
AU$314 per night
includes taxes & fees
Woodside Cabin #2 on Lake Heloise
Award winning design, European alpine with symmetric glass walls front and back
Private kitchen
Main living room with expansive windows and views
Spectacular alpine modern design
Exceptional
(10 reviews)

*The View* ski in/out modern luxury at Windham Mountain Resort

Windham

9% off
AU$38,073
for 7 nights, 1 home
AU$5,439 per night
includes taxes & fees
*The View* ski in/out modern luxury at Windham Mountain Resort
Terrace/patio
Exterior
Private kitchen
Living area
Exceptional
(16 reviews)

Cozy A FRAME ski retreat, walking distance into Hunter Mountain. New 2026 Rates

Hunter

8% off
AU$3,861
for 7 nights, 1 chalet
AU$552 per night
includes taxes & fees
Cozy A FRAME ski retreat, walking distance into Hunter Mountain. New 2026 Rates
Exterior
Winter view from patio. Ski Windham
Top Floor loft, next to master bedroom
Master king size bed
Exceptional
(11 reviews)

'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain

Windham

11% off
AU$13,706
for 7 nights, 1 home
AU$1,958 per night
includes taxes & fees
'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain
The stocked kitchen comes with a Keurig, a Mr. Coffee, and kettle
The hot tub leads to the deck, and is great to use year round
Interior
Interior
Exceptional
(114 reviews)

Mountain View Chalet Near Skiing

Hensonville

12% off
AU$7,503
for 7 nights, 1 home
AU$1,072 per night
includes taxes & fees
Mountain View Chalet Near Skiing
Living area
Interior
Interior
Dining
Exceptional
(6 reviews)

OMG Modern Country House wrap around deck beautiful sunrise walk to zoom flume.

East Durham

8% off
AU$4,876
for 7 nights, 1 home
AU$697 per night
includes taxes & fees
OMG Modern Country House wrap around deck beautiful sunrise walk to zoom flume.
Interior
Terrace/patio
Great room
Exterior
Exceptional
(119 reviews)

SECLUDED-PRIVATE LUXURY ESCAPE 5BR•4BA JACUZZI -ARCADE GAME RM WINDHAM HUNTER

Jewett

8% off
AU$6,842
for 7 nights, 1 home
AU$977 per night
includes taxes & fees
SECLUDED-PRIVATE LUXURY ESCAPE 5BR•4BA JACUZZI -ARCADE GAME RM WINDHAM HUNTER
Private kitchen
Exterior
Interior
Terrace/patio
Exceptional
(33 reviews)

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter

8% off
AU$2,254
for 7 nights, 1 chalet
AU$322 per night
includes taxes & fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Dining
Another property we have down the street; 4bedrm;3bath with large loft&game room
Private kitchen
Spacious living room; open to dining area
Exceptional
(80 reviews)

Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend

Hunter

8% off
AU$5,072
for 7 nights, 1 home
AU$725 per night
includes taxes & fees
Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend
Loft area with a study
Zoom Flume water park is 20 minutes from the house.
outdoor seating by the deck/patio
House in summer
Exceptional
(12 reviews)

Stunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna

Windham

13% off
AU$8,417
for 7 nights, 1 home
AU$1,202 per night
includes taxes & fees
Stunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna
Interior
Living area
Luxury bedding
Open concept kitchen/dining/living room. One of two living spaces
Exceptional
(17 reviews)

Located within 10 minutes from both Windham Mountain and Hunter Mountain!

Jewett

8% off
AU$6,369
for 7 nights, 1 home
AU$910 per night
includes taxes & fees
Located within 10 minutes from both Windham Mountain and Hunter Mountain!
Property grounds
Interior
Outdoor spa tub
Dining
Wonderful
(11 reviews)

Serendipity Lake house on private 28 acre lake

Windham

17% off
AU$7,531
for 7 nights, 1 home
AU$1,076 per night
includes taxes & fees
Serendipity Lake house on private 28 acre lake
Living room - working fireplace
Upstairs Living area, kitchen and dining area
Kitchen Island & stools
View from front deck
Exceptional
(8 reviews)

Great for Families & Groups!

Windham

8% off
AU$6,294
for 7 nights, 1 home
AU$899 per night
includes taxes & fees
Great for Families & Groups!
Mud room
Living space
Exterior detail
Exterior
Exceptional
(21 reviews)

Spacious Catskills Cabin w/Stream Near Hiking, Biking & Skiing

West Kill

8% off
AU$3,486
for 7 nights, 1 cabin
AU$498 per night
includes taxes & fees
Spacious Catskills Cabin w/Stream Near Hiking, Biking & Skiing
Room
Exterior
Property grounds
Living area
Wonderful
(5 reviews)

Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet

Maplecrest

8% off
AU$4,855
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet
Living area
Interior
Exterior
Private kitchen
Very good
(7 reviews)

6BR/7bath Luxury home Hot Tub in Hunter Catskills

Hunter

8% off
AU$12,318
for 7 nights, 1 home
AU$1,760 per night
includes taxes & fees
6BR/7bath Luxury home Hot Tub in Hunter Catskills
Bird watch, sip your coffee or enjoy an evening cocktail.
EVERYBODY’s Favorite The four seasons room!
The sun room - An extra sleeping room with all the beauty of sleeping outdoors
The Island and Everything You’ll Need To Create Amazing Meals.
Exceptional
(26 reviews)

Private Catskills Getaway with Gorgeous Mountain View’s

Round Top

8% off
AU$6,134
for 7 nights, 1 home
AU$876 per night
includes taxes & fees
Private Catskills Getaway with Gorgeous Mountain View’s
Interior
Exterior
Living area
Dining
Exceptional
(10 reviews)

West Kill Mountain Retreat

West Kill

8% off
AU$3,870
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
West Kill Mountain Retreat
Property grounds
Living area
Room
Interior
Exceptional
(18 reviews)

Cozy Waterfall Oasis + Firepit

East Durham

8% off
AU$3,009
for 7 nights, 1 home
AU$430 per night
includes taxes & fees
Cozy Waterfall Oasis + Firepit
Entry & Living Room
Indoor Heated Pool
View From Back Porch
Kitchen from Living Room
Exceptional
(10 reviews)

Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo

Windham

7% off
AU$7,055
for 7 nights, 1 apartment
AU$1,008 per night
includes taxes & fees
Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo
Living room towards dining table and slider to wrap around deck
Dining table area with slider to wrap around deck and stairs to loft
Master bedroom with queen size bed and 65” smart tv
Updated stainless steel kitchen with granite breakfast bar
Exceptional
(38 reviews)

Hunter Mountains Hill Top Hide Away Trail Side

Hunter

8% off
AU$4,913
for 7 nights, 1 apartment
AU$702 per night
includes taxes & fees
Hunter Mountains Hill Top Hide Away Trail Side

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

The relaxing city of Windham awaits you

Enjoy the wineries and other features of Windham. This relaxing city is known for its skiing, hiking and mountain views. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windham

Are you looking for attractions to visit while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Windham a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Windham Country Club (1 mi / 1.6 km)
  • Windham Mountain Resort (1.2 mi / 1.9 km)
  • Zoom Flume (7.4 mi / 11.9 km)
  • Hunter Mountain (7.4 mi / 12 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (9.5 mi / 15.3 km)
  • Kaaterskill Falls (12.5 mi / 20.1 km)

Exploring the natural landscape of Windham

Whether you're an active traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Windham. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Kaaterskill Falls (12.5 mi / 20.1 km)
  • Belleayre Beach (16.8 mi / 27.1 km)
  • Overlook Mountain Trailhead (17.6 mi / 28.4 km)
  • East Branch Delaware River (23 mi / 37.1 km)
  • Esopus Creek (28.1 mi / 45.3 km)
  • Mountain Top Arboretum (8.4 mi / 13.5 km)

Seasonal weather in Windham

Travellers enjoy Windham for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, December or November, when snowfall averages 18 cm and temperatures average -3°C.

Travelling to and around Windham

The nearest airport is in Hudson, NY (HCC-Columbia County), located 27.6 mi (44.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Windham when booking a holiday rental?
When considering a holiday rental in Windham, New York, a popular area to stay is the vibrant village centre. This charming spot boasts a variety of properties, from quaint cottages to more modern accommodations, providing options for all types of travellers. The village is not only picturesque but also conveniently located near top attractions such as the Windham Mountain Resort, which is superb for skiing in winter and mountain biking in summer. Another great point of interest is the Windham Historical Society, where visitors can delve into the local history and culture.Another appealing area is the surrounding countryside, where you can find lovely rentals located among the beautiful Catskill Mountains. This region offers a peaceful retreat, ideal for those who appreciate nature, with an abundance of hiking trails and stunning views. Staying here allows you to enjoy the tranquillity of the outdoors while still being a short drive away from the village's amenities and attractions.
Where are the best Windham ski resort rentals?
For the best ski resort rentals in Windham, New York, visitors should consider properties situated close to Windham Mountain. The area features a range of accommodations, including charming lodges and spacious condos that cater to families and groups. Many of these rentals come equipped with amenities such as fully stocked kitchens, fireplaces for cosy evenings, and access to ski storage, making them ideal for winter sports enthusiasts.Additionally, the village of Windham offers various dining options and local shops, enhancing the overall experience for travellers. Rentals near the base of Windham Mountain often provide ski-in/ski-out access, allowing guests to hit the slopes with ease. For those looking for a bit more luxury, some properties include hot tubs or saunas, great for relaxing after a day of skiing.Beyond the skiing, the surrounding Catskill Mountains present opportunities for hiking and exploring scenic trails during the off-season, making Windham a versatile destination year-round.
What is the most popular type of holiday rental accomodation in Windham?
In Windham, holiday houses are the most popular type of holiday rental, with around 512 available throughout the area. These spacious homes are typically situated in scenic locations, providing easy access to outdoor activities and local attractions. Most holiday houses come equipped with multiple bedrooms, fully fitted kitchens, and ample living space, making them ideal for families or groups.Additionally, there are about 128 condos available, which often feature modern amenities such as communal pools and fitness centres, superb for those seeking a more resort-like experience. Chalets, with approximately 80 options, provide a charming alpine feel, often with wooden interiors and proximity to skiing areas. Cabins, numbering around 72, offer a rustic escape, while about 60 apartments provide a convenient base for exploring the town and nearby attractions.
Are there any family house rentals in Windham?
In Windham, New York, there is an impressive selection of family-friendly holiday rentals, with around 157 properties available. This picturesque area, known for its stunning mountain views and outdoor activities, offers a variety of homes suitable for families. Visitors can find spacious rooms featuring multiple bedrooms, fully equipped kitchens for preparing family meals, and comfortable living areas great for relaxing after a day of adventure.Many of these rentals are conveniently located near popular attractions such as Windham Mountain, where families can enjoy skiing in winter or hiking and biking during the warmer months. The charming town centre is also just a short drive away, where local shops, restaurants, and seasonal events add to the vibrant community atmosphere.In addition, some properties may include outdoor amenities like decks or patios for enjoying the fresh air, while others might have game rooms or entertainment options to keep everyone entertained.
Can I rent a holiday home with a pool or hot tub in Windham?
In Windham, New York, there are plenty of holiday homes available for rent that come with pools or hot tubs, with around 48 options to choose from. This picturesque area, known for its stunning mountain views and outdoor activities, features a variety of properties in neighbourhoods such as Windham village and the surrounding scenic hills.Travellers can expect a range of amenities in these rentals including private swimming pools, relaxing hot tubs, and spacious outdoor areas great for entertaining or unwinding after a day of exploring. Many properties also offer fully equipped kitchens, comfortable living spaces, and proximity to local attractions such as hiking trails and ski resorts, making them ideal for families or groups seeking both relaxation and adventure.
Are there pet-friendly house rentals in Windham?
In Windham, there are numerous pet-friendly house rentals available, offering a variety of amenities to accommodate both travellers and their furry companions. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor spaces such as decks or gardens where pets can enjoy the fresh air.The area is known for its beautiful mountain scenery and outdoor activities, making it an ideal destination for pet owners. Nearby attractions like the Windham Mountain Resort provide opportunities for hiking and skiing, and there are several parks in the vicinity where pets are welcome to explore.With 96 pet-friendly holiday rentals to choose from, visitors can find options that suit their needs, whether they are looking for a cosy cabin or a larger home suitable for families.
Are there any remote work holiday rentals in Windham?
In Windham, New York, there are numerous options for remote work holiday rentals, with around 872 properties available to choose from. This quaint mountain town is ideal for those looking to combine work and leisure amidst stunning natural scenery. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, allowing for seamless connectivity while working remotely.Travellers can expect a variety of accommodations, from cosy cabins to spacious homes, often featuring dedicated workspaces or quiet areas great for setting up a home office. Furthermore, many properties include additional comforts like fully stocked kitchens, ample living space, and sometimes outdoor areas for relaxation after a day of work.Windham is also known for its beautiful landscapes, including nearby hiking trails and ski slopes, offering plenty of opportunities to unwind and recharge after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Windham?
In Windham, popular holiday rentals typically feature a range of amenities that enhance the comfort and convenience of guests. Most properties come equipped with kitchens, allowing travellers to prepare their own meals after a day of exploring the area's natural beauty. Many rentals also include a fireplace, great for creating a warm and inviting atmosphere during cooler months. Outdoor spaces such as decks or patios are common, providing a lovely setting for relaxation or al fresco dining while enjoying scenic views. Onsite parking is often available, making it easy for visitors to access the surrounding attractions. Additionally, many rentals offer coffee and tea makers, ensuring guests can enjoy their morning brew before heading out to explore nearby points of interest like the Windham Mountain Resort and the picturesque hiking trails in the Catskills.
When is the best time to visit Windham for a holiday rental?
January is the most popular time to visit Windham, perfectly aligning with the peak season that runs from December through February. This winter wonderland attracts visitors looking for exhilarating outdoor activities, particularly skiing and snowboarding, as the region is known for its excellent slopes and picturesque scenery. The cold, crisp air and snow-covered mountains create an ideal environment for those seeking adventurous winter sports.During January, you can expect daytime temperatures to hover around -7 to 1 degrees Celsius, making it a comfortable time for both skiing enthusiasts and those who enjoy relaxing by a warm fireplace after a day on the slopes. The charming town also offers a variety of local shops and eateries, allowing visitors to immerse themselves in the cosy winter atmosphere.If you're looking for a more budget-friendly option, consider visiting in October. This month offers a wonderful opportunity to witness the stunning fall foliage, with vibrant colours painting the landscape. It's a quieter time, great for gentle hikes and exploring the area's natural beauty without the crowds, allowing you to fully appreciate the serene surroundings.Ultimately, the best time to book a holiday rental in Windham depends on your preferences for winter sports and lively holiday festivities during peak season or a peaceful autumn escape with breathtaking views in the shoulder months.
What are the top attractions in Windham?
In Windham, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The Windham Mountain Resort is a major draw, offering skiing and snowboarding in winter, while in the warmer months, it transforms into a hub for mountain biking and hiking trails with stunning views of the Catskills.The charming village centre features quaint shops, local eateries, and the historic Windham Theatre, where guests can catch live performances. For those interested in history and culture, the Windham Historical Society offers insights into the area's past.Nature enthusiasts will appreciate the nearby Kaaterskill Falls, a short drive away, providing picturesque hiking opportunities and breathtaking scenery.
Are all fees included in the Windham holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Windham holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Windham holiday homes?
You can find great discounts on holiday homes in Windham on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Windham holiday home booking on Stayz?
To find Windham holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windham?
A long-stay holiday home in Windham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Windham holiday home?
Book your Windham holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windham?
Prices for holiday homes in Windham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windham to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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