Windham Vacation Rentals

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Nov 18 - Nov 19
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Nov 21 - Nov 23
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Nov 28 - Nov 30

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

Windham
9.2 out of 10, Wonderful, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
$122 nightly
The price is $132
Nov 19 - Nov 20
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

Windham
8.8 out of 10, Excellent, (53)
"Check in & checkout and communication super easy. Location is excellent. A/C and hot water great. For 4 guys on a 2 day golf trip it worked fine. "
United States
david d.
$170 nightly
The price is $184
Nov 19 - Nov 20
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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!

Ashland
9.2 out of 10, Wonderful, (5)
"Great place to stay very accommodating more than expected "
United States
Julia M.
$471 nightly
The price is $509
Nov 19 - Nov 20
Total with taxes and fees
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Exterior
Unwind Windham, Chalet

Unwind Windham, Chalet

Windham
10.0 out of 10, Exceptional, (2)
"We stayed only one night and we thought that should stay more nights because of the comfort of the house, the location, the amenities and the Property Host was there for answer any question. Definitely we come back now with the conviction that we have everything we need for an escape from New York city. I recommend this place in a 100% for sure. "
United States
Karla R.
$498 nightly
The price is $503
Nov 20 - Nov 21
Total with taxes and fees
Unwind Windham, Chalet
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!

Windham
10.0 out of 10, Exceptional, (2)
"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.
$1,310 nightly
The price is $1,404
Nov 19 - Nov 20
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!

Windham
10.0 out of 10, Exceptional, (4)
"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.
$1,310 nightly
The price is $1,404
Nov 19 - Nov 20
Total with taxes and fees
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
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!

Windham
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
$1,310 nightly
The price is $1,404
Nov 19 - Nov 20
Total with taxes and fees
Newly Constructed Modern Farmhouse -- 4 BR / 4.5 Baths, High-end Furnishings!
Room
MIRROR CABIN IN THE FOREST WITH HOT TUB

MIRROR CABIN IN THE FOREST WITH HOT TUB

Windham
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.
$285 nightly
The price is $323
Dec 3 - Dec 4
Total with taxes and fees
MIRROR CABIN IN THE FOREST WITH HOT TUB
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
$520 nightly
The price is $561
Nov 20 - Nov 21
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Outdoor spa tub
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, (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.
$477 nightly
The price is $515
Nov 19 - Nov 20
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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

Windham
10.0 out of 10, Exceptional, (3)
"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.
$1,286 nightly
The price is $1,389
Nov 20 - Nov 21
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

Windham
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.
$387 nightly
The price is $391
Dec 8 - Dec 9
Total with taxes and fees
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
Terrace/patio
Drift Haus|4.5BR+ Mountain Lodge

Drift Haus|4.5BR+ Mountain Lodge

Windham
8.0 out of 10, Very Good, (1)
"The property was beautiful and peaceful. The kitchen was amazing and there were so many common areas that were great to socialize in. We did encounter some garbage left by the previous guests, but Will was responsive when we flagged it. There were a few repairs needed on the sliding doors, but overall it was a luxurious place to stay while we enjoyed the nature. "
United States
Grace H.
$746 nightly
The price is $752
Nov 19 - Nov 20
Total with taxes and fees
Drift Haus|4.5BR+ Mountain Lodge
Exterior
Serene Catskills Escape: Hot Tub, Pond & Game Room

Serene Catskills Escape: Hot Tub, Pond & Game Room

Windham
10.0 out of 10, Exceptional, (16)
"The house is better than described. We had our annual extended family get together and more room than we needed. The adults and kids enjoyed the game rooms, hot tub movie room. The home was prepared with everything we needed. Very clean We will return. Beautiful home! "
United States
Suzanne n.
$1,258 nightly
The price is $1,359
Dec 9 - Dec 10
Total with taxes and fees
Serene Catskills Escape: Hot Tub, Pond & Game Room
1 bedroom, free WiFi
LUXURY SUITE WITH 2 FULL BEDS

LUXURY SUITE WITH 2 FULL BEDS

Windham
$145 nightly
The price is $164
Nov 19 - Nov 20
Total with taxes and fees
LUXURY SUITE WITH 2 FULL BEDS
1 bedroom, free WiFi
GLASS MIRROR CABIN - HAUS WINDHAM

GLASS MIRROR CABIN - HAUS WINDHAM

Windham
8.0 out of 10, Very Good, (1)
$257 nightly
The price is $291
Dec 8 - Dec 9
Total with taxes and fees
GLASS MIRROR CABIN - HAUS WINDHAM
Interior
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

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

Windham
$430 nightly
The price is $465
Nov 19 - Nov 20
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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

Windham
10.0 out of 10, Exceptional, (1)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
$3,035 nightly
The price is $3,278
Nov 25 - Nov 26
Total with taxes and fees
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Exterior
Condo in Windham Mountain Village

Condo in Windham Mountain Village

Windham
10.0 out of 10, Exceptional, (14)
"Condo was clean and comfortable and very convenient to indoor pool and skiing. Thank you for a great vacation!"
United States
Rich R.
$707 nightly
The price is $764
Nov 19 - Nov 20
Total with taxes and fees
Condo in Windham Mountain Village
Terrace/patio
Tiny House on Walnut Grove

Tiny House on Walnut Grove

2.0 star property
Ashland
4.0 out of 10, (2)
"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.
$264 nightly
The price is $286
Nov 22 - Nov 23
Total with taxes and fees
Tiny House on Walnut Grove
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Really great spot!"
Aria 1-night trip
Posted 2 days ago
Hotel Vienna

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 $131 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 149 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.