A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Windham Vacation Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

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, (61 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is SAR 488
SAR 831 total
includes taxes & fees
3 Aug - 4 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is SAR 766
SAR 2,316 total
includes taxes & fees
12 Jul - 13 Jul
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Exterior

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is SAR 695
SAR 1,963 total
includes taxes & fees
21 Jul - 22 Jul
Pines Vignette • Modern 3BR Home in Windham
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
The price is SAR 745
SAR 969 total
includes taxes & fees
13 Jul - 14 Jul
Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4
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, (3 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.
The price is SAR 1,123
SAR 1,445 total
includes taxes & fees
12 Jul - 13 Jul
Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
Indoor pool, a heated pool

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
10.0 out of 10, Exceptional, (1 review)
"Host had an amazing response time. Very easy to talk with via email. She had very clear and easy instructions on check in and check out. The place had lots of bedding, it was warm and inviting, had everything we needed. My daughter thought the “balcony” on the second floor which over looked the kitchen was cool! "
United States
Soonae S.
The price is SAR 1,690
SAR 2,526 total
includes taxes & fees
12 Jul - 13 Jul
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
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.
The price is SAR 920
SAR 2,255 total
includes taxes & fees
3 Aug - 4 Aug
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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.
The price is SAR 2,403
SAR 3,278 total
includes taxes & fees
13 Jul - 14 Jul
Ask about Spring Specials!
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)
"We had an amazing get away! Yasmin is a great host very informative. The house is well stocked and the views were amazing. Quick trip to town and the mountain."
United States
Babette n.
The price is SAR 3,191
SAR 6,018 total
includes taxes & fees
13 Jul - 14 Jul
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
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
The price is SAR 2,403
SAR 3,278 total
includes taxes & fees
13 Jul - 14 Jul
Ask about Spring Specials!
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.
The price is SAR 1,014
SAR 2,332 total
includes taxes & fees
21 Jul - 22 Jul
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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.
The price is SAR 2,403
SAR 3,278 total
includes taxes & fees
13 Jul - 14 Jul
Ask about Spring Specials!
Dining

Lux Mansion, Windham: Hot Tub, Sauna

Lux Mansion, Windham: Hot Tub, Sauna
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.
The price is SAR 3,717
SAR 6,902 total
includes taxes & fees
22 Jul - 23 Jul
Lux Mansion, Windham: Hot Tub, Sauna
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.
The price is SAR 8,448
SAR 12,737 total
includes taxes & fees
21 Jul - 22 Jul
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Smart TV, fireplace

Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (15 reviews)
"Location is great"
United States
Jennifer M.
The price is SAR 2,497
SAR 3,812 total
includes taxes & fees
10 Jul - 11 Jul
Condo in Windham Mountain Village
1 bedroom, in-room safe, free WiFi, bed sheets

Iconic Glass Mirror Cabin ·Mountain View ·Private Fire Pit ·3 Min to Windham Mtn

Iconic Glass Mirror Cabin ·Mountain View ·Private Fire Pit ·3 Min to Windham Mtn
Windham
8.0 out of 10, Very Good, (1 review)
The price is SAR 982
SAR 1,239 total
includes taxes & fees
13 Jul - 14 Jul
Iconic Glass Mirror Cabin ·Mountain View ·Private Fire Pit ·3 Min to Windham Mtn
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
The price is SAR 745
SAR 965 total
includes taxes & fees
14 Jul - 15 Jul
Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · 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

Emerson Resort & Spa

Emerson Resort & Spa

10/10 Excellent
"Great place! Wish we could have stayed longer. Great breakfast!"
Patricia 1-night trip
Posted 1 day ago
Emerson Resort & Spa

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?

Swim. Float. Fish. on private waterfront w/Hot Tub.Fire Pit.Views. Hiking.Games.: This vacation home rental outside of Windham is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. It offers a patio, 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 151 Expedia vacation rentals, you're sure 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 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.