Cozy cabins and mountain chalets provide the warmth, modern rustic charm and relaxing atmosphere that travelers want to come back to after a long day at play. Decompress in an house with a private hot tub, or stare out the windows of your mountain view vacation home as you plot your next excursion.

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Best Vacation Home Deals in Windham
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Top-Rated Rentals and Accommodations in Windham
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Recommended Vacation Rentals in Windham
Find your perfect vacation rental in Windham: from $83 per night
Budget-friendly Vacation Rentals in Windham
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Vacation rentals with Wi-Fi
Stay connected while traveling and book a Windham accommodation with high-speed internet.
Vacation Rentals With Fireplaces
Get warm and cozy on cold winter nights in Windham by booking a vacation home with a fireplace.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Windham rental with full kitchen.

Popular Rental Amenities in Windham
Listed above are the most selected filters in Windham and the number of vacation rentals that include them. Many properties in Windham provide "Pets allowed" or "Pool," which makes it a great vacation spot if you travel with your pet or you're dreaming of days spent poolside. Plan your vacation in advance if you want a rental with a yard or you need a crib for your baby. There are just 209 listed rentals including "Yard" and 27 accommodations including "Crib."
Price and Availability Index in Windham
Vacation Rental Price Information in Windham
The price graph will give you the nightly price average for the upcoming months of the year. in Windham, prices can go up to $696 (5/25 – 6/1). Opt for a getaway in October (10/26 – 11/2) for optimal savings when heading to Windham.
Rental availability information in Windham
Find out the percentage of available rentals in Windham with the graph above. Be careful if you plan to go to Windham in October, as it comprises the busiest week of the next 12 months (10/26 – 11/2). Conversely, it is in December (12/9 – 12/16) that the highest percentage of rentals are available.
The Weather in Windham
You can see our climate diagram above. The highest average temperatures are in the month of July. However, temperatures can go lower than 18° in Windham in January. The rainiest month is December while the driest month is August.
7-Day Weather Forecast in Windham
Accommodations for your vacation in Windham
Fun for kids of all ages
If you are looking for something more sporting, mountain biking, zip-lines, go carts, huge trampolines, a free skate park as well as golf courses are all within easy reach of Windham. In the summer visitors enjoy the nearby water park or, during winter, you can slide down the snow tubes at the local mountain resorts.
Nightlife in and around Windham
There is plenty to do after a hard day at play. Family-friendly restaurants provide dinner options for all. For nights without the kids, local taverns, pubs and bars have something for everyone. Poker, pool, DJs, karaoke and quizzes are there to make nights as fun as the days.
Outdoor and indoor fun for every season
Heavy average snowfalls provide vacationers with ample opportunities to enjoy winter sports. Convenient for skiers and snowboarders looking to hit the slopes there are two mountain resorts within 15 minutes of the area which are comparable to the best the northeast region has to offer.
Many snowshoe and cross country ski trails are available nearby. These activities are a nice way to experience something new and they are worth the effort in order to take in scenic snow-covered mountains and lakes.
In spring and autumn surround your senses with nature on wilderness trails that wend through hemlock, balsam fir and hardwood forests. If you keep a watchful eye you may catch a glimpse of various wildlife including beaver, deer and turkey. More challenging treks are rewarded with sights such as the Kaaterskill Falls and Point Lookout which overlooks 5 states.
Information about vacation rentals in Windham
🏡 Vacation rentals available | 403 homes |
---|---|
💳 Possible discounts | up to 59% |
🌙 Nightly prices starting at | $108 |
⭐ Popular amenities | Pets allowed, Pool and Internet |
🐾 Pet friendly homes | 64 homes |
🏊 Vacation rentals with pools | 82 homes |
Frequently Asked Questions
What is the typical nightly price for a vacation home in Windham?
The average accommodation in Windham is priced at $108 per night. If you are looking for a house rental, the nightly price is $848 on average. A bed and breakfast rental Windham will cost on average $238 per night.
How many vacation rentals are available to book in Windham?
Currently there are 403 vacation homes from 7 providers in Windham.
What amenities are most popular for vacation homes in Windham?
Usually travelers look for Pool, Pets allowed, and Internet when booking a vacation rental in Windham.
How many vacation rentals with pools are in Windham?
There are 82 rentals across 7 providers in Windham.
Are pets allowed in vacation rentals in Windham?
If traveling with a pet in Windham, 16% of rentals are pet-friendly.
What's the best time of year to travel to Windham?
Windham has its warmest time of year in July and August, with average nightly prices around $108.
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