Windham Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Windham vacation rentals

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)
"Lovely hosts "
United States
Tyler G.
$192 nightly
The price is $207
May 18 - May 19
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

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

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (44 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
$122 nightly
The price is $132
May 17 - May 18
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Smart TV, fireplace

Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4

Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4
Windham
$223 nightly
The price is $254
May 18 - May 19
Total with taxes and fees
Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4
1 bedroom, in-room safe, iron/ironing board, travel crib

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
Windham
$159 nightly
The price is $180
May 17 - May 18
Total with taxes and fees
Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
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
$527 nightly
The price is $569
May 16 - May 17
Total with taxes and fees
Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
In-room safe, bed sheets

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
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.
$323 nightly
The price is $367
May 17 - May 18
Total with taxes and fees
Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
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, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
$468 nightly
The price is $505
May 18 - May 19
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Aerial view

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.
$735 nightly
The price is $794
May 17 - May 18
Total with taxes and fees
Condo in Windham Mountain Village
Exterior

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
$478 nightly
The price is $516
May 18 - May 19
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
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.
$489 nightly
The price is $528
May 20 - May 21
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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.
$455 nightly
The price is $491
May 25 - May 26
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham
Dining

Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge

Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge
Windham
10.0 out of 10, Exceptional, (4 reviews)
"The house was exactly as pictured and described. Beautiful home on a huge lot. "
United States
Whit M.
$1,474 nightly
The price is $1,592
May 18 - May 19
Total with taxes and fees
Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge
Dining

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
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.
$1,464 nightly
The price is $1,581
May 20 - May 21
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
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.
$263 nightly
The price is $284
May 16 - May 17
Total with taxes and fees
Tiny House on Walnut Grove
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.
$806 nightly
The price is $873
May 18 - May 19
Total with taxes and fees
Ask about Spring Specials!
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.
$795 nightly
The price is $861
May 18 - May 19
Total with taxes and fees
Ask about Spring Specials!
Exterior

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
$795 nightly
The price is $861
May 18 - May 19
Total with taxes and fees
Ask about Spring Specials!
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.
$3,141 nightly
The price is $3,392
May 26 - May 27
Total with taxes and fees
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Exclusive House, Mountain View | Iron/ironing board, free WiFi

Red Feather Lodge

Red Feather Lodge
3.0 star property
Windham
$1,999 nightly
The price is $2,159
May 16 - May 17
Total with taxes and fees
Red Feather Lodge
1 bedroom, in-room safe, iron/ironing board, travel crib

Presidential Duplex · Full Kitchen ·Wraparound Terrace ·Marble Jacuzzi ·Sleeps 4

Presidential Duplex · Full Kitchen ·Wraparound Terrace ·Marble Jacuzzi ·Sleeps 4
Windham
$259 nightly
The price is $294
May 18 - May 19
Total with taxes and fees
Presidential Duplex · Full Kitchen ·Wraparound Terrace ·Marble Jacuzzi ·Sleeps 4
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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Top Windham Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"It was exactly what we wanted. "
Charlie 2-night trip
Posted 20 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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 152 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.