Windham Vacation Rentals

Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Windham vacation rentals

Smart TV, fireplace

Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (15 reviews)
"Place was amazing "
United States
Erik B.
$736 nightly
The price is $795
Mar 25 - Mar 26
Total with taxes and fees
Condo in Windham Mountain Village
Property grounds

Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC

Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
Windham
$535 nightly
The price is $578
Mar 25 - Mar 26
Total with taxes and fees
Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
Exterior

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

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (59 reviews)
"Everything was perfect! Great location!"
United States
Susan I.
$178 nightly
The price is $192
Mar 25 - Mar 26
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Dining

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Windham
10.0 out of 10, Exceptional, (7 reviews)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
$1,367 nightly
The price is $1,476
Mar 26 - Mar 27
Total with taxes and fees
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Dining

Waterfront Mansion on 20 acres Windham Ski Resort

Waterfront Mansion on 20 acres Windham Ski Resort
Windham
10.0 out of 10, Exceptional, (4 reviews)
"It was a wonderful house. The first few days were very cold and it was spacious and there was a lot to do within the house and it was very comfortable to stay in! When it warmed up we were literally 5 minutes from the slopes and 3 minutes from the town."
United States
RoseMarie D.
$1,472 nightly
The price is $1,590
Mar 25 - Mar 26
Total with taxes and fees
Waterfront Mansion on 20 acres Windham Ski Resort
Interior

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Windham
10.0 out of 10, Exceptional, (1 review)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
$3,122 nightly
The price is $3,372
Mar 31 - Apr 1
Total with taxes and fees
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Dining

Unwind Windham, Chalet

Unwind Windham, Chalet
Windham
10.0 out of 10, Exceptional, (3 reviews)
"This was a gem of a property. Super clean and cozy. Fantastic amenities! The host was always responsive. We plan on renting this property again in the future. "
United States
Derrick S.
Unwind Windham, Chalet
TV

Modern Duplex King Suite with Jacuzzi, Steam Shower, Gym — Windham NY Catskills

Modern Duplex King Suite with Jacuzzi, Steam Shower, Gym — Windham NY Catskills
Windham
$223 nightly
The price is $254
Mar 25 - Mar 26
Total with taxes and fees
Modern Duplex King Suite with Jacuzzi, Steam Shower, Gym — Windham NY Catskills
Terrace/patio

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

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Ashland
$466 nightly
The price is $503
Mar 30 - Mar 31
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Microwave, oven, stovetop, dishwasher

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (2 reviews)
"I really enjoyed my time here. The house was comfortable, modern and well taken care of, and the property it was on was beautiful. Good access to town as well, and the full kitchen was well appointed. I had a really relaxing weekend, I'd book this again."
United States
Robert G.
$1,072 nightly
The price is $1,154
Apr 1 - Apr 2
Total with taxes and fees
Ask about Spring Specials!
TV, fireplace

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (4 reviews)
"We had a great three day getaway in Windham. The house was a great spot for a ski getaway in the mountains. Nice open floor plan and every bedroom had a bathroom which was great"
United States
Jim V.
$1,072 nightly
The price is $1,154
Apr 1 - Apr 2
Total with taxes and fees
Ask about Spring Specials!
TV, fireplace

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (1 review)
"We had an amazing time in this magnificent, beautiful home. Our family books ski trips throughout the northeast twice a year as a group of 10 for the past 10 years. This house has by far ranked #1 as the best house we have stayed in. 10 minutes away from the mountain (Windham). 4 large sized bedrooms each with their own large bathrooms. A beautiful dream kitchen with all the essentials. We did plenty of cooking. We loved the open layout of the home. We will definitely be back for sure. "
United States
Anonymous traveler
$1,086 nightly
The price is $1,169
Apr 1 - Apr 2
Total with taxes and fees
Ask about Spring Specials!
Game room

Lux Windham Getaway | Views & Indoor Heated Pool

Lux Windham Getaway | Views & Indoor Heated Pool
Windham
10.0 out of 10, Exceptional, (3 reviews)
"We recently stayed at this house with a group of friends and our children. The house was absolutely gorgeous, the kids loved the pool and the theater room. The beds were comfortable and the kitchen was well equipped. Can’t wait to stay here again! "
United States
Abby D.
$1,556 nightly
The price is $1,680
Apr 1 - Apr 2
Total with taxes and fees
Lux Windham Getaway | Views & Indoor Heated Pool
Smart TV, fireplace

Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!

Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location amazing townhouse. I will definitely be coming back."
United States
Marquise D.
$525 nightly
The price is $567
Mar 25 - Mar 26
Total with taxes and fees
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
1 bedroom, free WiFi

LUXURY SUITE WITH 2 FULL BEDS

LUXURY SUITE WITH 2 FULL BEDS
Windham
$159 nightly
The price is $180
Mar 25 - Mar 26
Total with taxes and fees
LUXURY SUITE WITH 2 FULL BEDS
Exterior

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"Staying at this property was an absolute delight. The space was spotless, beautifully decorated, and felt even better in person than in the photos. Every detail - from the comfortable bedding to the amenities - made my stay feel effortless and relaxing. Check in was smooth. Overall an outstanding experience. Highly recommend this property! "
United States
Dikaury G.
$430 nightly
The price is $464
Mar 25 - Mar 26
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham
Room

Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain

Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain
Windham
8.0 out of 10, Very Good, (2 reviews)
"This was a unique and fun VRBO experience. The cabin was cozy and comfortable.So delightful to wake up to deer walking right by the window! Absolutely a gem of a property!"
United States
Erin J.
$322 nightly
The price is $366
Mar 25 - Mar 26
Total with taxes and fees
Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain
Dining

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

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
$465 nightly
The price is $502
Apr 9 - Apr 10
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Terrace/patio

Tiny House on Walnut Grove

Tiny House on Walnut Grove
Ashland
4.0 out of 10, (2 reviews)
"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...
United States
Trevor C.
$267 nightly
The price is $288
Mar 25 - Mar 26
Total with taxes and fees
Tiny House on Walnut Grove
TV, fireplace

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (4 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
$486 nightly
The price is $524
Mar 25 - Mar 26
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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.
View all properties
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Clean, updated bathrooms and comfortable bed."
Maria 1-night trip
Posted 12 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windham?

Yes, we give you a choice of vacation rentals close to top points of interest in Windham, or you can select a more remote option if you'd like a relaxing place to 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 coffeehouses.

What are some of the best vacation rentals in Windham?

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts : Visitors like this Windham vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Windham?

With 147 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What can I see and do in Windham?

Ashland Park and Elm Ridge Wild Forest 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 vacation rentals like in Windham?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Windham. Vacation rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.