Holiday Rentals Windham from £122: Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Windham has to offer?

Modern Luxurious Cabin, Catskills - The Tiny Nook : This holiday home rental outside of Windham is located in a rural location, and offers a patio, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Windham holiday rentals

A two-story building with large windows and a storefront.

1. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Windham

Rebecca

includes taxes & fees

10 Nov - 11 Nov

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

Windham

"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."

April

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a wooden ceiling, a large window, a bed, and a bathroom with a sink and mirror.

3. Presidential Suite with Jacuzzi, Full Kitchen and Sauna near Windham Mtn

Windham

includes taxes & fees

10 Nov - 11 Nov

A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

4. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham

Cristina L.

includes taxes & fees

10 Nov - 11 Nov

A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

5. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

Windham

Melissa R.

includes taxes & fees

10 Nov - 11 Nov

A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

6. Condo in Windham Mountain Village

Windham

Jennifer M.

includes taxes & fees

10 Nov - 11 Nov

A large, two-story house with a stone facade, a wooden deck, and a clear sky.

7. Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

Windham

Lobid C.

includes taxes & fees

10 Nov - 11 Nov

A two-story house with a stone chimney, wooden deck, and a stone staircase leading to the entrance.

8. Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain

Windham

includes taxes & fees

11 Nov - 12 Nov

A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

9. Pines Vignette • Modern 3BR Home in Windham

Windham

William H.

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

10. 5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

Windham

includes taxes & fees

30 Nov - 1 Dec

A cozy living room with wooden walls, a stone fireplace, and a television.

11. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Windham

John K.

includes taxes & fees

17 Nov - 18 Nov

A living room with a sectional sofa, a wooden coffee table, and a view through large arched windows to an outdoor deck.

12. Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes

Windham

includes taxes & fees

10 Nov - 11 Nov

A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

13. Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain

Windham

Erin J.

includes taxes & fees

10 Nov - 11 Nov

A log cabin interior with a large sofa, armchairs, a coffee table, and a television.

14. Luxury Mansion: Mountain View, Sauna, Hot Tub, Cold Plunge, Golf, Game Room

Windham

includes taxes & fees

10 Nov - 11 Nov

15. Lux Mansion, Windham: Hot Tub, Sauna

Windham

RoseMarie D.

includes taxes & fees

10 Nov - 11 Nov

16. Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ashland

Julia M.

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio area with a pergola, seating, and a barbecue grill.

17. Tiny House on Walnut Grove

Ashland

"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...

Trevor C.

includes taxes & fees

10 Nov - 11 Nov

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

Ashland

includes taxes & fees

11 Nov - 12 Nov

A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

19. Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn

Windham

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with a fireplace, a cozy seating area, and a view of the outdoors.

20. 2BR with 2 Baths, Fireplace, Sauna and Gym, 3 Min to Windham Mountain

Windham

Dan D.

includes taxes & fees

10 Nov - 11 Nov

View all properties

Find holiday rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Windham Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent

"We had a great time. The pool, hot tubs and saunas were amazing. The bar and restaurant was very good. No need to drive out of the hotel for a drink or dinner. Just wished the bar was open until later. Bedroom was very nice. We stayed in a deluxe studio and it was nicely stocked with everything we needed. We will definitely be coming back. Planning to come with the family for snow fun."

Dancing Horse Farm - 9BR Catskills Lodge on 30 Acres

10/10 Excellent

"Dancing Horse Farm is a beautiful place surrounded by gorgeous mountains and breathtaking scenery The pictures just give you a hint of the amazing beauty of this property The interior of the home is clean , spacious, equipped with every modern convenience The rooms are comfortable Each with its own unique design and quality The bathrooms are sanitary and bright Every where you look you can see the owner Greg has put his heart into the care of this house He has thought of every detail Your every need is met staying at this property The grounds offer opportunities for hiking , serene walks and deep relaxation The added touch is the barn with its three adorable goats A big attraction for younger children The area Windham offers restaurants, breweries, shops, markets a great fun location The house , the location, the owner Greg all are outstanding I can go on and onOur family fell in love with it all and will make Dancing Horse Farm our annual tradition"

Find out more about Windham

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, apart-hotels, 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 favorite 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 depends 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 £122 per night. Entering your travel dates in the search wizard you might find 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?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This holiday home rental outside of Windham is located in a rural location, and offers a patio, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Windham?

With 139 Expedia holiday rentals, you're guaranteed to find just the right place for your Windham stay.

What can I see and do in Windham?

Elm Ridge Wild Forest and Ashland Park are a couple of lovely local spots to get outside and enjoy nature. 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham holiday rentals

1. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

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

3. Presidential Suite with Jacuzzi, Full Kitchen and Sauna near Windham Mtn

4. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome