Windham Vacation Rentals

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Nov 3 - Nov 4
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Vacation Rentals in Windham

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
9.2 out of 10, Wonderful, (40)
"Wonderful coszy spot perfect location for singles and couples even family "
United States
Ahmad O.
$118 nightly
The price is $127
Nov 4 - Nov 5
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Property grounds
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
8.8 out of 10, Excellent, (53)
"Very good location and host."
United States
Alexander
$171 nightly
The price is $185
Nov 9 - Nov 10
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior
Unwind Windham, Chalet
Unwind Windham, Chalet
10.0 out of 10, Exceptional, (1)
$569 nightly
The price is $575
Nov 10 - Nov 11
Total with taxes and fees
Unwind Windham, Chalet
Fridge, microwave, oven, stovetop
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
10.0 out of 10, Exceptional, (1)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
$3,100 nightly
The price is $3,348
Nov 9 - Nov 10
Total with taxes and fees
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Property grounds
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
9.2 out of 10, Wonderful, (5)
"We really enjoyed staying here just because how relaxing it felt, to be outside enjoying the nice weather and having the horses run by. Just overall very soothing and quiet at night."
United States
Richard S.
$328 nightly
The price is $354
Nov 4 - Nov 5
Total with taxes and fees
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
1 bedroom, free WiFi
LUXURY SUITE WITH 2 FULL BEDS
LUXURY SUITE WITH 2 FULL BEDS
$145 nightly
The price is $164
Nov 4 - Nov 5
Total with taxes and fees
LUXURY SUITE WITH 2 FULL BEDS
Outdoor spa tub
2 Min Walk to Windham Town | Hot Tub | Fire Pit
2 Min Walk to Windham Town | Hot Tub | Fire Pit
10.0 out of 10, Exceptional, (1)
"It was amazing for a big family! Tons of space, and everything was very clean! The hosts were also very pleasant to deal with."
United States
Hadassah S.
$412 nightly
The price is $445
Nov 4 - Nov 5
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Room
MIRROR CABIN IN THE FOREST WITH HOT TUB
MIRROR CABIN IN THE FOREST WITH HOT TUB
8.0 out of 10, Very Good, (2)
"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.
$279 nightly
The price is $317
Dec 1 - Dec 2
Total with taxes and fees
MIRROR CABIN IN THE FOREST WITH HOT TUB
Terrace/patio
Tiny House on Walnut Grove
Tiny House on Walnut Grove
2.0 star property
4.0 out of 10, (1)
$236 nightly
The price is $255
Nov 4 - Nov 5
Total with taxes and fees
Tiny House on Walnut Grove
TV
LUXURY DUPLEX SUITE WITH JACUZZI
LUXURY DUPLEX SUITE WITH JACUZZI
$203 nightly
The price is $231
Nov 10 - Nov 11
Total with taxes and fees
LUXURY DUPLEX SUITE WITH JACUZZI
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
$475 nightly
The price is $514
Nov 4 - Nov 5
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Microwave, oven, stovetop, dishwasher
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
10.0 out of 10, Exceptional, (1)
"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
$1,303 nightly
The price is $1,396
Nov 4 - Nov 5
Total with taxes and fees
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Interior
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
10.0 out of 10, Exceptional, (2)
"We had an absolutely incredible stay at this beautiful Catskills retreat! We booked with Several friends and celebrated their 50th birthday here and it was a wonderful decision. The home was spotless, stylish, and fully equipped with everything we needed for a relaxing and comfortable visit. From the cozy fireplace and spacious deck to the stunning views of the woods and mountains. Set in beautiful and peaceful surroundings, every detail was thoughtfully curated to create the perfect escape....
United States
Carl L.
$1,303 nightly
The price is $1,396
Nov 4 - Nov 5
Total with taxes and fees
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
TV, fireplace
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
10.0 out of 10, Exceptional, (4)
"Wonderful property. Beautiful house. Great set up for 2 families - one king bedroom and one bedroom with 2 twins upstairs and one king bedroom and one bedroom with 2 twin beds downstairs. Each room has it's own full bathroom. Everything is brand new. First floor is spacious and great for hanging out with open kitchen/dining room/den. Close to Windham and about 25 minute drive from Hunter Mountain. The property manager was very responsive to our concerns and questions. Would definitely rent...
United States
Lauren G.
$1,303 nightly
The price is $1,396
Nov 4 - Nov 5
Total with taxes and fees
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Fridge, microwave, oven, stovetop
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
10.0 out of 10, Exceptional, (3)
"Everything was super "
United States
Hazal U.
$1,339 nightly
The price is $1,447
Nov 5 - Nov 6
Total with taxes and fees
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
Terrace/patio
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
10.0 out of 10, Exceptional, (5)
"Beautiful property, very accurately represented in listing photos. Very well stocked with every thing you need to host. Lots of fun activities to do in the home. Would definitely recommend"
United States
Andrea S.
$446 nightly
The price is $450
Nov 11 - Nov 12
Total with taxes and fees
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
Dining
Drift Haus|4.5BR+ Mountain Lodge Room only
Drift Haus|4.5BR+ Mountain Lodge Room only
$896 nightly
The price is $904
Nov 9 - Nov 10
Total with taxes and fees
Drift Haus|4.5BR+ Mountain Lodge Room only
Exterior
Serene Catskills Escape: Hot Tub, Pond & Game Room
Serene Catskills Escape: Hot Tub, Pond & Game Room
10.0 out of 10, Exceptional, (16)
"Me and my friends had a lot of fun staying at Bella Vista. The games setup is great. We had something for everyone to play and enjoy. The property was very neat and clean and there was room for everyone."
United States
Sanya P.
$1,245 nightly
The price is $1,345
Nov 5 - Nov 6
Total with taxes and fees
Serene Catskills Escape: Hot Tub, Pond & Game Room
Exterior
Condo in Windham Mountain Village
Condo in Windham Mountain Village
10.0 out of 10, Exceptional, (14)
"We had such a great stay at this home which was walking distance (even with little kids) to the mountain! The house was clean and very comfortable."
United States
Kristine M.
$705 nightly
The price is $761
Nov 7 - Nov 8
Total with taxes and fees
Condo in Windham Mountain Village
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

Wylder Hotel Windham

Wylder Hotel Windham

10/10 Excellent
"Really nice restored resort. Rooms were great, staff was friendly. The food is very good."
Shane 1-night trip
Posted 14 hours ago
Wylder Hotel Windham

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?

Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing : This vacation home rental outside of Windham is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 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?

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 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.