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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Windham vacation rentals

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, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is AED 281
AED 502 total
includes taxes & fees
23 Jun - 24 Jun
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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, (60 reviews)
The price is AED 477
AED 805 total
includes taxes & fees
23 Jun - 24 Jun
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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.
The price is AED 592
AED 1,056 total
includes taxes & fees
24 Jun - 25 Jun
Tiny House on Walnut Grove
Hair dryer, towels, soap, shampoo

King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4

King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4
Windham
7.6 out of 10, Good, (5 reviews)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
The price is AED 690
AED 884 total
includes taxes & fees
23 Jun - 24 Jun
King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4
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 AED 680
AED 1,916 total
includes taxes & fees
22 Jul - 23 Jul
Pines Vignette • Modern 3BR Home in 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.
The price is AED 900
AED 2,198 total
includes taxes & fees
6 Jul - 7 Jul
2 Min Walk to Windham Town | Hot Tub | Fire Pit
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 AED 900
AED 2,150 total
includes taxes & fees
6 Jul - 7 Jul
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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 AED 1,114
AED 2,734 total
includes taxes & fees
23 Jul - 24 Jul
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Hair dryer, towels, soap, shampoo

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
The price is AED 536
AED 692 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
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.
The price is AED 1,098
AED 1,405 total
includes taxes & fees
23 Jun - 24 Jun
Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
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
The price is AED 1,623
AED 2,558 total
includes taxes & fees
23 Jun - 24 Jun
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Interior

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 reviews)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is AED 1,286
AED 2,015 total
includes taxes & fees
4 Jul - 5 Jul
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
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 AED 1,653
AED 2,408 total
includes taxes & fees
6 Jul - 7 Jul
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
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 AED 2,351
AED 3,207 total
includes taxes & fees
6 Jul - 7 Jul
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
The price is AED 2,351
AED 3,167 total
includes taxes & fees
6 Jul - 7 Jul
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.
The price is AED 2,351
AED 3,191 total
includes taxes & fees
23 Jun - 24 Jun
Ask about Spring Specials!
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)
"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 AED 3,636
AED 6,688 total
includes taxes & fees
22 Jul - 23 Jul
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)
"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 AED 3,122
AED 5,974 total
includes taxes & fees
23 Jun - 24 Jun
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
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 AED 1,570
AED 2,719 total
includes taxes & fees
23 Jun - 24 Jun
Condo in Windham Mountain Village
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 AED 8,264
AED 12,460 total
includes taxes & fees
28 Jun - 29 Jun
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
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

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"Very laid back kind of vibes! Loved it a lot. The heated pool, sauna, hot tub added to the relaxation. Ate at the restaurant and the food was pretty good! I will return"
alicia 2-night trip
Posted less than an hour ago
Kaatskill Mountain Club & Condos by Vail Resorts

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 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?

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.