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  2. Maine
  3. Portland
  4. Windham
  5. Cottage Rentals

Windham Cottage Rentals

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9.3 (3 Reviews)
House
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
4.7 (3 Reviews)
Hotel
  • Pet Friendly
  • Security/Safety
  • Sports/Activities
9.6 (4 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
10.0 (5 Reviews)
Cottage
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities

Why Choose Rent By Owner for your Windham Cottage Rentals?

What makes our Cottage Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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 vacation in Windham, Maine, USA can enhance your experience by aligning your plans with the region's seasonal charm and activities, ensuring you find the perfect cottage accommodations here for a memorable getaway.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences warm weather ideal for outdoor activities and enjoying the scenic beauty of the area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn offers a vibrant display of foliage, making it a perfect time to explore the region's natural charm and tranquility.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Spring (March to May)

In spring, the area awakens with blooming flowers and milder temperatures, providing a quiet and peaceful escape.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
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Winter (December to February)

The winter season brings cooler temperatures suitable for cozy stays and wintertime scenery in the region.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F

Weekly Weather Forecast for Windham

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.

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 dining on a private patio or deck, perfect for relaxing meals surrounded by nature.
  • Take advantage of spacious yards ideal for outdoor games and family activities amidst scenic views.
  • Make use of private gardens or landscaped areas to unwind and connect with the natural beauty of the region.
  • Benefit from convenient access to nearby hiking trails and walking paths for exploring the area's lush landscape.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars with friends and loved ones.
  • Relax by outdoor swimming pools or hot tubs, offering refreshing escapes in the fresh Maine air.
  • Leverage ample parking space for your outdoor gear or boat storage, enhancing your adventure experience here.
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Family Activities

  • Windham Recreation Center: Engage in family-friendly activities with indoor swimming pools, sports courts, and fitness classes suitable for all ages.
  • Victoria Park: Enjoy scenic walking trails, playgrounds, and picnic areas perfect for relaxing outings with your loved ones amidst natural beauty.
  • Local Water Activities: Explore opportunities for kayaking, paddleboarding, or fishing at nearby lakes and rivers in the region, offering fun water adventures for families.
  • Community Events: Participate in seasonal festivals and family-oriented events that often take place in Windham, providing memorable experiences for children and parents alike.
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Adult Activities

  • Hiking and Nature Walks: Explore scenic trails in the area that offer a peaceful retreat amidst natural beauty, perfect for outdoor enthusiasts seeking tranquility and fresh air.
  • Kayaking and Canoeing: Spend your days paddling on local lakes or rivers, enjoying a leisurely way to take in the region’s picturesque landscapes from the water.
  • Fishing Excursions: Engage in fishing activities that the region is known for, whether you prefer relaxing lakeside or riverbank spots with abundant local aquatic life.
  • Wildlife Viewing and Birdwatching: Discover diverse flora and fauna by visiting nearby wildlife refuges and birding areas, ideal for nature lovers wanting to observe native species.

Other Places to Stay in Windham, ME

Seacoast Adventure
Sebago Lake Basin
Little Falls-South Windham
North Windham
Mercy Primary Care
Maine Wildlife Park

Windham Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Off-Peak Seasons: Visiting during less busy times can ensure a more relaxed experience and better availability of charming cottages in the area.
  • Explore Local Outdoor Activities: Take advantage of the numerous outdoor pursuits available nearby to immerse yourself in the natural beauty that surrounds this destination.
  • Book Accommodations Early: Secure your preferred cottages ahead of time to enjoy the comfort and convenience of well-appointed lodging in this scenic region.
  • Familiarize Yourself with Local Amenities: Learning about nearby shops, eateries, and services will help you make the most of your stay and enjoy everything the area has to offer.

Transportation Options

  • Car Rental Services: You can easily rent a vehicle to explore the area and reach your desired cottages with flexibility and convenience.
  • Public Transit: Bus services in this region offer an affordable way to travel between key destinations and nearby towns.
  • Taxi and Ride-Sharing: Taxis and ride-sharing options provide on-demand transportation for quick trips around the local community.
  • Bicycle Rentals: Biking is an eco-friendly and leisurely way to enjoy the scenic surroundings as you navigate the local areas near your stay.

Local Customs Options

  • Greetings and Politeness: Visitors often find that exchanging friendly greetings like "hello" or "good morning" is a valued gesture here, reflecting the region's warm community spirit.
  • Respect for Nature: It’s customary to show consideration for the local environment by preserving natural sites and following designated trails during outdoor activities.
  • Local Cuisine Etiquette: When enjoying meals, sharing traditional dishes and participating in communal dining are common ways visitors engage with the area's culinary customs.
  • Community Events Participation: Participating in local events or festivals is encouraged as a way to connect with residents and experience this destination's vibrant culture.

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 28 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?

The cancellation policy varies by listing, so it’s important to review the specific terms on the property page or contact the owner directly for details regarding cancellations and potential fees.

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

Additional fees such as cleaning, service charges, or security deposits are often listed on the property page. Be sure to read the full listing details or reach out to the host for clarification before completing your reservation.

5. Can I find pet-friendly cottages here, and what are the requirements?

Many cottages accommodate pets, but each property has its own policies. Check the listing details for pet restrictions, fees, and other requirements or contact the owner directly to confirm pet acceptance.

6. Is Wi-Fi available during my stay at a cottage in this destination?

Most listings specify whether Wi-Fi is included. For essential connectivity, review the amenities section or contact the owner to ensure the property meets your internet needs.

7. What should I do if I need to modify my reservation or have questions about my booking?

You can manage your booking through the platform, and if you need further assistance, contacting the property owner or customer support will help resolve your inquiries efficiently.

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