Windham Rentals By Owner

Windham Rentals by Owner

Highly Rated

10.0

Exceptional

(165 Reviews)

Private secluded trout cabin- sleeps 2

2 Guests 1 Bedroom 1 Bathroom

Family Friendly Cabin

Fireplace/Heating
Balcony/Terrace
Pet Friendly

CA $253/Night For 7 Nights CA $1,771

View Deal

10.0

Exceptional

(2 Reviews)

Wish Upon A Star

3261.46 ft² 8 Guests 1 Bedroom 3 Bathrooms

Family Friendly House

Hot Tub
Skiing
Fireplace/Heating

CA $999/Night For 7 Nights CA $6,995

View Deal

Cozy Ski-in/ski-out Condo on Magic Mountain

10.0

Exceptional

(2 Reviews)

Cozy Ski-in/ski-out Condo on Magic Mountain

1 Bedroom 1 Bathroom

Family Friendly Apartment

Fireplace/Heating
Kitchen
Internet

CA $298/Night For 7 Nights CA $2,083

View Deal

10.0

Exceptional

(1 Review)

Brand New Luxury “Tiny” House, Immersed In Nature

3 Guests 2 Bedrooms 1 Bathroom

Family Friendly Cabin

Kitchen
Internet
Child Friendly

CA $617/Night For 7 Nights CA $4,321

View Deal

Ski-InandSki-Out Magic Mountain Condo with Deck!

10.0

Exceptional

(2 Reviews)

Ski-InandSki-Out Magic Mountain Condo with Deck!

645.83 ft² 4 Guests 1 Bedroom 1 Bathroom

Apartment

Skiing
Fireplace/Heating
Parking

CA $212/Night For 7 Nights CA $1,485

View Deal

Single-Level Duplex with Fast WiFi & a Full Kitchen - Close to Magic Mountain

8.6

Fabulous

(16 Reviews)

Single-Level Duplex with Fast WiFi & a Full Kitchen - Close to Magic Mountain

720 ft² 5 Guests 2 Bedrooms 1 Bathroom

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Kitchen

CA $208/Night For 7 Nights CA $1,456

View Deal

Londonderry Chalet with Deck, Fire Pit and Views!

10.0

Exceptional

(1 Review)

Londonderry Chalet with Deck, Fire Pit and Views!

1614.59 ft² 8 Guests 3 Bedrooms 2 Bathrooms

Free Cancellation House

Fireplace/Heating
Parking
Internet

CA $509/Night For 7 Nights CA $3,562

View Deal

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Highly Rated

10.0

Exceptional

(57 Reviews)

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

30 Guests 11 Bedrooms 6 Bathrooms

Ocean View House

Private Pool
Hot Tub
Spa

CA $4,036/Night For 7 Nights CA $28,256

View Deal

Cozy Ski-InandSki-Out Condo on Magic Mountain

10.0

Exceptional

(1 Review)

Cozy Ski-InandSki-Out Condo on Magic Mountain

925.7 ft² 6 Guests 2 Bedrooms 2 Bathrooms

Family Friendly Apartment

Skiing
Fireplace/Heating
Parking

CA $471/Night For 7 Nights CA $3,296

View Deal

Maple Season Basecamp: 3 mi to Magic, Paved Road Access

10.0

Exceptional

(22 Reviews)

Maple Season Basecamp: 3 mi to Magic, Paved Road Access

2400 ft² 10 Guests 4 Bedrooms 2 Bathrooms

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Pet Friendly

CA $592/Night For 7 Nights CA $4,145

View Deal

9.2

Exceptional

(13 Reviews)

Magic Birch Lodge

721.18 ft² 5 Guests 1 Bedroom 1 Bathroom

Free Cancellation House

Skiing
Fireplace/Heating
Kitchen

CA $285/Night For 7 Nights CA $1,992

View Deal

Londonderry Chalet w/Deck, Fire Pit & Views!

10.0

Exceptional

(18 Reviews)

Londonderry Chalet w/Deck, Fire Pit & Views!

1612 ft² 8 Guests 3 Bedrooms 2 Bathrooms

Family Friendly Cabin

Fireplace/Heating
Balcony/Terrace
Kitchen

CA $483/Night For 7 Nights CA $3,383

View Deal

More Top-Rated Rentals by Owner in Windham Area

Why Choose Rent By Owner for your Windham vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner stay?

Understanding the best time to visit here can help you make the most of your rental by owner experience in Windham, Vermont, ensuring you enjoy this destination at its most beautiful and vibrant throughout the year.

Peak Season Highlights

Winter (December to February)

During the winter months, this destination transforms into a snowy retreat, ideal for enjoying winter sports and cozy accommodations. You will experience its vibrant atmosphere with picturesque snow-covered landscapes.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 5°F to 15°F

Fall (September to November)

Autumn brings colorful foliage that makes this area particularly popular among visitors seeking scenic views and outdoor activities. The crisp air enhances the overall experience of your stay here.

Average Temperature Daytime: 50°F to 65°F - Nighttime: 35°F to 45°F

Off-Season Highlights

Spring (March to May)

Springtime offers a quieter period when you can enjoy the region’s natural beauty as it awakens from winter, perfect for those looking to avoid crowds while exploring outdoors.

Average Temperature Daytime: 40°F to 60°F - Nighttime: 25°F to 40°F

Early Summer (June)

Early summer provides a serene setting before peak tourist season begins, with pleasant weather ideal for outdoor activities and exploring the scenic surroundings.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Weekly Weather Forecast for Windham

How to Book Your Windham vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Windham

More Top-Rated Rentals by Owner in Windham Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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

You can enjoy spacious outdoor seating areas perfect for relaxing and socializing in the fresh mountain air.
Many rentals offer access to private or shared picnic areas, ideal for enjoying meals outdoors amidst scenic views.
Look for properties with outdoor fire pits to gather around and make the most of cool evenings in this region.
Expect options that include outdoor grills, allowing you to cook and dine al fresco during your stay.
Some rentals feature expansive yards or gardens, providing space for outdoor games and leisure activities.
You'll often find outdoor parking facilities that ensure convenience while exploring the local surroundings.
Many properties are equipped with decks or patios to take in the natural beauty that this destination is known for.

Top Attractions Around Windham

What attractions are nearby?

While staying here, you can enjoy a variety of outdoor activities nearby, such as hiking, skiing, and exploring scenic trails in the region, making it an ideal destination for adventure enthusiasts seeking memorable experiences.

Family Activities

Windham Mountain Resort: Enjoy family-friendly skiing, snowboarding, and mountain adventures suitable for all ages in this popular destination.
Green Mountain Adventure**: Experience outdoor fun such as zip-lining, canopy tours, and scenic chairlift rides that make outdoor exploration exciting for the whole family.
Windham Fall Foliage Tours: Take a scenic drive or guided tour through the region’s vibrant fall foliage, perfect for creating memorable family photographs.
Local Nature Trails: Explore family-friendly hiking trails around here that showcase the area's natural beauty while offering an easy escape into nature.

Adult Activities

Snowboarding and Skiing at Mount Snow: Experience the thrill of hitting the slopes during winter months, with access to world-class ski facilities right in the area.
Hiking along the Appalachian Trail: Explore scenic trails that wind through the region’s lush landscapes, offering peaceful retreats and breathtaking vistas.
Golf at local courses: Enjoy a round of golf on picturesque courses that showcase the natural beauty of this Vermont destination.
Visit Local Breweries and Wineries: Indulge in tastings at regional breweries and wineries, immersing yourself in the area's burgeoning craft beverage scene.

Windham Travel Tips

How Can You Make the Most of Your Stay?

Explore local outdoor activities: Take advantage of the region’s natural beauty by engaging in hiking or outdoor adventures right from your rental, making the most of the fresh mountain air.
Plan ahead for seasonal attractions: Be aware of the area's seasonal offerings and book any popular activities or events in advance to ensure a seamless experience during your stay.
Utilize local dining options nearby: Discover the culinary delights available close to your rental to enjoy authentic regional flavors without the hassle of long travel times.
Connect with your host for personalized tips: Reach out to your property owner for insider recommendations on hidden gems and must-visit spots in this scenic destination.

Transportation Options

Car Rental Services: You can conveniently rent a vehicle here to explore the scenic region at your own pace.
Public Transit: Local buses offer an affordable way to navigate within this area and reach nearby attractions with ease.
Taxi and Ride-Sharing: Taxis and ride-sharing options provide quick, reliable transportation for getting around the destination comfortably.
Airport Transportation: Nearby airports connect you to the broader region, making arrivals and departures smooth and hassle-free.

Local Customs Options

Respect for Nature and Outdoor Etiquette: You will find that maintaining a respectful attitude towards the scenic landscape is highly valued here, especially when enjoying outdoor activities in the region.
Community Celebrations and Festivals: Participating in local festivals reflects the area's close-knit spirit, providing an authentic way to engage with residents during your stay.
Environmental Conservation Practices: Eco-friendly behaviors, such as proper waste disposal and supporting local sustainable initiatives, are appreciated by those who call this destination home.
Traditional Local Hospitality: Expect warmth and friendliness from the community, embodying the welcoming nature that makes visiting here so memorable.

Frequently Asked Questions About Windham Rentals by Owner

1. What are the top Vacation Rentals 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 Vacation Rentals in Windham:

2. How many Vacation Rentals are available in Windham?

Currently, the total number of properties listed by RBO in 2026 is over 50 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Windham. 

3. What is the cancellation policy for rental by owner accommodations in Windham, Vermont?

The cancellation policy varies depending on the individual listing. To understand the specific terms, please review the cancellation details provided in the rental description or contact the property owner directly.

4. How do I communicate with the property owner before booking my stay in this area?

You can use the messaging platform on the booking website to reach out to the owner. This allows you to ask questions, clarify details, and ensure the property meets your needs before confirming your reservation.

5. Are there any additional fees I should be aware of when booking a rental by owner here?

Additional fees such as cleaning charges, service fees, or security deposits may apply. These details are typically listed on the property page or are communicated by the owner during the booking process.

6. What amenities are generally included in rental properties in this destination?

Amenities vary by listing but often include essentials like Wi-Fi, parking, kitchen facilities, and outdoor spaces. For specifics, always check the property description or contact the owner directly.

7. How do I ensure the rental property complies with safety standards in this region?

All rental properties listed on the platform undergo host verification and adhere to local safety regulations. However, it’s advisable to review the property’s safety features and ask the owner any safety-related questions before booking.