Windham Cottage Rentals By Owner

Windham Cottage Rentals

Highly Rated

Cabin

Private secluded trout cabin- sleeps 2

10.0

Exceptional

(166 Reviews)

1 Bedroom 1 Bath 2 Guests

R3,932/Night 7 Nights - R27,521

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House

Wish Upon A Star

10.0

Exceptional

(2 Reviews)

4 Bedrooms 3 Baths 8 Guests 3261.46 ft²

R11,550/Night 7 Nights - R80,849

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

Apartment

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

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath

R3,524/Night 7 Nights - R24,666

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Condo

Cozy Ski-In/Ski-Out Condo on Magic Mountain

10.0

Exceptional

(14 Reviews)

2 Bedrooms 2 Baths 6 Guests 922 ft²

R5,118/Night 7 Nights - R35,824

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Londonderry Chalet w/Deck, Fire Pit & Views!

House

Londonderry Chalet w/Deck, Fire Pit & Views!

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 8 Guests 1614.59 ft²

R6,025/Night 7 Nights - R42,170

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House

Ski & Lake Home-Minutes Lowell Lake, Magic, Stratton, Bromley & Okemo

10.0

Exceptional

(2 Reviews)

2 Bedrooms 1 Bath 6 Guests 1200 ft²

R3,718/Night 7 Nights - R26,020

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House

Cozy Ski-In/Ski-Out Condo on Magic Mountain

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 6 Guests 925.7 ft²

R5,574/Night 7 Nights - R39,021

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Condo

Ski-In/Ski-Out Magic Mountain Condo w/Deck!

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 650 ft²

R3,247/Night 7 Nights - R22,724

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House

Magic Birch Lodge

9.2

Exceptional

(13 Reviews)

2 Bedrooms 1 Bath 5 Guests 721.18 ft²

R3,371/Night 7 Nights - R23,589

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Condo

Magic Mountain Trailside Condo - Ski In/Ski Out

9.8

Exceptional

(14 Reviews)

1 Bedroom 1 Bath 6 Guests 650 ft²

R2,673/Night 7 Nights - R18,711

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New Cozy Private Chalet Incredible Mountain Views!

House

New Cozy Private Chalet Incredible Mountain Views!

4 Bedrooms 3 Baths 15 Guests 3498.27 ft²

R14,138/Night 7 Nights - R98,973

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

Price Dropped

House

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

8.6

Fabulous

(16 Reviews)

2 Bedrooms 1 Bath 5 Guests 720 ft²

R2,597/Night 7 Nights - R18,173

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More Top-Rated Cottage Rentals in Windham Area

Why Choose Rent By Owner for your Windham Cottage Rentals?

What makes our Cottage Rentals 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 Cottage Rentals stay?

Choosing the right time to visit ensures you can fully enjoy the natural beauty and tranquility of this destination, making your stay in Windham perfect whether you seek outdoor adventures or peaceful relaxation in your ideal cottages here.

Peak Season Highlights

Winter (December to February)

During the winter months, this destination transforms into a snow-covered haven, making it an ideal time for snow sports and cozy evenings by the fire.

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

Fall (September to November)

The vibrant foliage attracts nature lovers seeking breathtaking views and outdoor activities amid colorful landscapes, creating a memorable getaway here.

Average Temperature Daytime: 50°F to 65°F - Nighttime: 30°F to 45°F

Off-Season Highlights

Spring (March to May)

As the region awakens from winter, you can enjoy milder weather and blooming scenery, perfect for exploring the area's natural beauty.

Average Temperature Daytime: 45°F to 60°F - Nighttime: 25°F to 40°F

Summer (June to August)

Warm summer days encourage outdoor adventures and relaxation, making it a suitable period for experiencing this area's scenic charm.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Weekly Weather Forecast for Windham

How to Book Your Windham Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. 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 Cottage Rentals in Windham Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage Rentals 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 outdoor grilling with available barbecue facilities to make the most of warm summer evenings.
Relax amidst beautifully maintained gardens that enhance your outdoor experience in the area.
Take advantage of private patios or decks to unwind and soak in the scenic views surrounding your rental.
Make use of on-site fire pits, perfect for cozy gatherings after a day exploring the region.
Revel in access to expansive lawns ideal for outdoor activities or simply enjoying the fresh mountain air.
If you’re seeking adventure, many rentals offer direct access to hiking trails nearby for outdoor enthusiasts.
Some properties feature outdoor seating areas designed for alfresco dining amid the picturesque landscape.

Top Attractions Around Windham

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities such as hiking, mountain biking, and nature walks, while nearby attractions offer opportunities for skiing and snowboarding during the winter months, making it an ideal destination for adventure seekers looking to explore all that Vermont has to offer.

Family Activities

Windham Mountain Resort Spend a day enjoying family-friendly skiing, snowboarding, or mountain biking here for outdoor fun suitable for all ages.
Echo Lake State Park Discover the natural beauty of this scenic park with opportunities for lakeside picnics, swimming, and gentle hikes perfect for families.
Mountain Coaster Adventure Park Experience thrill rides and scenic rides along winding tracks, offering exhilarating entertainment for children and adults alike.
Local Farm Tours Visit nearby farms to learn about regional agriculture, participate in seasonal activities, and enjoy fresh local produce as a family activity.

Adult Activities

Hiking and Nature Walks: Explore the scenic trails around this destination to enjoy the region’s natural beauty and tranquil landscapes.
Fishing Adventures: Cast your line in local lakes and streams, offering a peaceful way to unwind and connect with nature.
Golfing: Tee off at nearby golf courses that provide a relaxing and picturesque setting for a day on the greens.
Local Dining Experiences: Savor regional cuisine at cozy restaurants and eateries that highlight the area's culinary charm.

Windham Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Visits During the Off-Peak Seasons: You can enjoy a more peaceful stay and better access to local attractions by visiting during less busy times of the year.
Explore Local Outdoor Activities: Take advantage of the region’s natural beauty through activities like hiking, which provide a great way to immerse yourself in the area’s scenic landscapes.
Choose a Central Location for Your Cottages: Picking a property near key amenities or outdoor spots ensures you maximize your time and convenience during your stay here.
Research Nearby Dining and Entertainment Options: Discovering local eateries and events can enrich your visit, offering authentic experiences within the region.

Transportation Options

Car Rentals: Renting a car gives you the flexibility to explore Windham and its scenic surroundings at your own pace, making it an ideal transportation option for reaching secluded cottages here.
Local Shuttle Services: Efficient shuttle services operate within the area, providing convenient transportation that allows you to enjoy the region’s natural beauty without the hassle of driving.
Buses: Bus services connect Windham with nearby towns and cities, offering an affordable and reliable way to travel if you prefer public transportation during your stay.
Taxi and Rideshare: Taxis and rideshare options like Uber or Lyft are readily available, providing quick and direct routes to your chosen cottages throughout this destination.

Local Customs Options

Local Harvest Celebrations: Participating in seasonal harvest festivals highlights the region’s agricultural roots and offers a chance to enjoy fresh, local produce throughout your stay.
Traditional Vermont Hospitality: Visitors often experience warm welcomes and friendly interactions that reflect the area's longstanding customs of neighborliness and community spirit.
Farmers Markets: Engaging with vibrant farmers markets provides an authentic glimpse into local life and supports sustainable, regional agriculture initiatives.
Mountain Trail Etiquette: Respect for designated trail use and environmental preservation is a key aspect of outdoor activities in this area’s scenic mountain landscapes.

Frequently Asked Questions About Windham Rental Cottages

1. What are the top Cottages 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 Cottages in Windham:

2. How many Cottages are available in Windham?

Currently, the total number of properties listed by RBO in 2026 is over 77 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Windham. 

3. What is the cancellation policy for cottages in this area?

Cancellation policies can vary depending on the property owner. You should review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

4. Are there any additional fees I should be aware of when booking a cottage here?

Additional fees such as cleaning, security deposits, or service charges may apply. It's best to check the detailed listing information or reach out to the owner for clarity on extra costs.

5. What amenities are typically included with cottages in this region?

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, heating, and outdoor spaces. Confirm the specific amenities listed for your chosen cottage to ensure it meets your needs.

6. Is there a minimum stay requirement for booking a cottage in this destination?

Minimum stay requirements differ among owners. Be sure to review the booking details or contact the owner directly to verify if a minimum night stay applies during your desired dates.

7. How do I ensure my booking is secure and reliable?

Booking through a reputable platform provides secure transactions and support. Review the property's ratings and reviews, and communicate directly with the owner if needed, to confirm the details before finalizing your reservation.