Windham Resorts
House
8.6(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1097.92 ft²
Spa
Fireplace/Heating
Parking
Internet
US $136/Night
7 Nights - US $952
House
5 Bedrooms
3 Baths
8 Guests
3003.13 ft²
- Fireplace/Heating
View
Air Conditioner- Internet
US $626/Night
7 Nights - US $4,381
House
12 Bedrooms
10 Baths
33 Guests
10763.91 ft²
- Fireplace/Heating
- Parking
- Internet
Child Friendly
US $4,930/Night
7 Nights - US $34,512
House
4 Bedrooms
2 Baths
9 Guests
3605.91 ft²
- Fireplace/Heating
Balcony/Terrace
Pet Friendly- Parking
US $386/Night
7 Nights - US $2,705
Apartment
10.0(107 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
US $200/Night
7 Nights - US $1,399
Ski Chalet
10.0(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
1905.21 ft²
- Balcony/Terrace
- Parking
- Internet
- Child Friendly
US $254/Night
7 Nights - US $1,779
Bed & Breakfast
9.0(129 Reviews)
1 Bedroom
1 Bath
Skiing- Balcony/Terrace
Breakfast- Kitchen
US $146/Night
7 Nights - US $1,021
Cabin
10.0(69 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $185/Night
7 Nights - US $1,292
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1797.57 ft²
- Spa
- Fireplace/Heating
- Parking
- Internet
US $687/Night
7 Nights - US $4,809
Apartment
10.0(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
1 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $277/Night
7 Nights - US $1,942
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1797.57 ft²
Oceanfront- Fireplace/Heating
Ocean View- View
US $409/Night
7 Nights - US $2,865
Condo
10.0(10 Reviews)
2 Bedrooms
2 Baths
8 Guests
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
US $459/Night
7 Nights - US $3,213
Why Choose Rent By Owner for your Windham Resorts?
What makes our Resorts special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windham
When should you plan your Resorts stay?
To make the most of your stay, consider visiting during the shoulder seasons when this destination offers fewer crowds and better rates, allowing you to fully enjoy the natural beauty and tranquility that make the region an ideal spot for memorable vacations.
Peak Season Highlights
Winter (December to February)
During the winter months, you can experience peak season as visitors flock to this destination for its renowned snow activities and winter scenery.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 0°F to 15°F
Summer (June to August)
The summer period is also a busy time here, attracting travelers looking to enjoy outdoor adventures and lush landscapes amidst warm weather.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Spring (March to May)
Visiting in spring allows you to enjoy fewer crowds while witnessing the region's natural beauty blooming during this quieter season.
Average Temperature Daytime: 40°F to 60°F - Nighttime: 25°F to 40°F
Fall (September to November)
Fall offers a peaceful escape with vibrant foliage and milder weather, making it an ideal off-peak period for relaxed stays here.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Windham
How to Book Your Windham Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windham
Common Resorts Amenities
What amenities can you expect?
Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or balcony where you can relax and take in scenic views of the region.
- Take advantage of spacious outdoor lawns or gardens perfect for picnics or outdoor activities.
- Make use of a well-maintained swimming pool to cool off during warm days in this destination.
- Benefit from access to outdoor grilling stations or barbecue areas for outdoor dining experiences.
- Explore nearby hiking trails or nature walks directly from your accommodations in the area.
- Utilize on-site tennis courts or sports facilities to stay active during your stay here.
- Relax around an outdoor fire pit, ideal for evenings filled with conversation and storytelling.
Top Attractions Around Windham
What attractions are nearby?
Within this scenic area, you can enjoy a variety of outdoor activities such as hiking, skiing, and exploring charming local shops, all just moments from your chosen resort in Windham, New York, offering a perfect blend of adventure and relaxation for your getaway.
Family Activities
- Windham Mountain Resort: Experience outdoor fun with a variety of family-friendly activities, from skiing and snowboarding in winter to mountain biking and hiking during the warmer months.
- Windham Path: Take a scenic stroll or bike ride along this accessible trail that offers stunning views and a peaceful environment suitable for all ages.
- Hunter Mountain: Enjoy family adventures at this nearby mountain, featuring zip-lining, chairlift rides, and other outdoor pursuits perfect for creating lasting memories.
- Local Farmer’s Markets: Explore regional farmers' markets that provide fresh local produce and handmade crafts, offering an engaging way for families to connect with the area's culture and community.
Adult Activities
- Hiking and Nature Walks: Discover the scenic trails through the lush landscape, offering a peaceful escape for invigorating hikes and nature walks in the area.
- Golfing: Enjoy a game at premier golf courses that provide stunning views and challenging holes, perfect for golf enthusiasts visiting this destination.
- Skiing and Snowboarding: During winter months, experience exhilarating skiing and snowboarding on local slopes designed for all skill levels.
- Local Wineries and Craft Breweries: Indulge in tastings at nearby wineries and craft breweries, showcasing the region’s rich beverage craftsmanship.
Other Places to Stay in Windham, NY
Windham Mountain Resort
Windham Country Club
Windham Vineyards and Winery
Ashland
Windham Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead: Book your resorts in Windham, New York early to secure the best accommodations and take advantage of off-peak rates.
- Explore Local Amenities: Take time to discover the region’s nearby shops and dining options to enrich your stay in this scenic area.
- Pack Accordingly: Prepare for the season by bringing suitable outdoor gear to fully enjoy the natural beauty here, whether it’s hiking gear or winter apparel.
- Stay Connected with Nature: Make the most of your visit by engaging in outdoor activities available in the area, which offers a perfect blend of relaxation and adventure.
Transportation Options
- Car Rentals: You can easily rent a vehicle at local agencies in Windham to explore the area's scenic surroundings comfortably and on your schedule.
- Public Transit: Convenient bus services operate within the region, providing an affordable transportation option for getting around here without the need for a car.
- Taxi Services: Reliable taxi and rideshare options are available nearby, making short trips within the destination quick and hassle-free.
- Private Shuttle Services: Specialized shuttle providers offer direct transfers to popular spots in the area, ideal for guests staying at nearby resorts seeking convenience.
Local Customs Options
- Mountain Hospitality: Locals here take pride in welcoming visitors with warm hospitality rooted in their mountain traditions, creating a friendly atmosphere during your stay.
- Seasonal Festivals: Participating in seasonal festivals is a cherished custom, offering you an authentic glimpse into the area's cultural celebrations throughout the year.
- Local Artisanship: The region boasts a strong tradition of craftsmanship, where handmade goods and local art are integral to community life and can enhance your experience.
- Outdoor Gatherings: Community outdoor gatherings such as farmers' markets and picnics reflect the area's appreciation for nature and social connection amid scenic views.
Windham Resorts Frequently Asked Questions
1. What are the top Resorts in Windham?
There are a lot of options in Windham. If you plan on staying in the Windham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Windham:
- Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
- Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub
- Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
- Cozy Caboose in the city
- Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.
- Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ
- Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
- *GUT RENO 4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*Windhm Mtn View*2BBQs
- Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
- Windham Family Getaway
2. How many Resorts are available in Windham?
Currently, the total number of properties listed by RBO in 2026 is over 4 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Windham.
3. What is the cancellation policy for resorts in Windham, New York?
Cancellation policies vary depending on the specific property. It is advisable to review the resort's cancellation terms directly on the listing or contact the owner for detailed information before completing your booking.
4. Are there any additional fees I should be aware of when booking a resort in this area?
Additional fees such as service charges, cleaning fees, or local taxes may apply. These details are typically specified in the property description or during the booking process, so please check the listing carefully or reach out to the host for clarification.
5. What amenities can I expect during my stay at a resort in the region?
Resorts in the area often offer amenities like outdoor activities, on-site dining, wellness facilities, and scenic views. To ensure the property meets your needs, review the amenities listed on the property page or contact the owner directly.
6. How do I ensure my reservation is secure and confirmed?
Reservations are confirmed once you complete the booking process and receive a confirmation from the host. For added peace of mind, verify the property's reviews and communicate directly with the owner if needed before finalizing your reservation.
7. Is there a specific check-in and check-out process for these resorts?
Check-in and check-out procedures can vary by property. Details are usually provided after booking or upon arrival. If you have special requests or need further guidance, contact the property owner in advance to ensure a smooth stay.
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- Parking
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Condo
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House
10.0(1 Review)
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2 Bedrooms
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6 Guests
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House
10.0(7 Reviews)
1 Bedroom
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4 Guests
1 ft²
- Fireplace/Heating
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10.0(6 Reviews)
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House
10.0(2 Reviews)
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Apartment
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2 Bedrooms
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- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $286/Night
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Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $254/Night
7 Nights - US $1,777
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
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US $608/Night
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