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  2. Maine
  3. Augusta
  4. Winthrop
  5. Rentals by Owner

Discover Your Perfect Winthrop Rentals by Owner

Winthrop Rentals by Owner

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New
House
The Pinecone
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
View Availability
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9.5 (2 Reviews)
House
Cobbossee Hideaway
  • View
  • Balcony/Terrace
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in Winthrop Area

Why Choose Rent By Owner for your Winthrop vacation rental?

What makes our Rentals by Owner 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 Winthrop

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here can enhance your experience and ensure you enjoy the region’s best weather and activities, making it easier to find the perfect rental by owner with Rent By Owner in Winthrop, Maine.

Peak Season Highlights

summer
Summer (June to August)

During the warmest months, you'll enjoy long days and vibrant outdoor activities, making it an ideal time to explore and relax here.

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

As the region transforms with colorful foliage, this is a popular time for scenic drives and outdoor adventures in the area.

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

Off-Season Highlights

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Winter (December to February)

The quieter winter months offer a peaceful atmosphere, perfect for those seeking solitude or cozy indoor stays in the region.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F
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Spring (March to May)

In early spring, expect fewer visitors and budding scenery, making it an excellent time for budget-friendly rentals and quiet exploration.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Winthrop

How to Book Your Winthrop 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

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 Winthrop

More Top-Rated Rentals by Owner in Winthrop 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

  • Enjoy outdoor lounging with a private patio or deck perfect for relaxing in the fresh air.
  • Take advantage of spacious yards ideal for outdoor activities or family gatherings.
  • Make use of a barbecue grill to host memorable cookouts amidst the scenic surroundings.
  • Explore nearby walking trails or nature paths directly accessible from your rental.
  • Relax by a fire pit during cool evenings, ideal for unwinding and socializing outdoors.
  • Utilize covered porches or verandas to enjoy the tranquility of the area regardless of weather.
  • Access outdoor sports equipment like kayaks or paddleboards if available locally for adventure on the water.

Top Attractions Around Winthrop

What attractions are nearby?

While staying here, you can enjoy a variety of outdoor activities nearby, including scenic boat tours and tranquil lakeside walks that showcase the natural beauty of this destination.

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Family Activities

  • Visit the Winthrop Public Library: Engage your family with a wide selection of books and participate in community programs that make exploring here both educational and fun.
  • Explore Pebble Beach: Spend quality time together by relaxing on this scenic lakeside spot, perfect for picnicking, swimming, or simply enjoying the view of Lake Cobbosseecontee.
  • Go for a Family Hike at Mount Pisgah: Discover stunning vistas and nature trails suitable for all ages, offering an outdoor adventure that showcases the region's natural beauty.
  • Enjoy a Day at the Winthrop Area Recreation Park: Take advantage of playgrounds, sports fields, and open spaces ideal for families to play, bike, or have a leisurely picnic outdoors.
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Adult Activities

  • Boating and Fishing on Maranacook Lake: You can enjoy a relaxing day on the water, taking advantage of the region's renowned lakeside surroundings perfect for boating and fishing enthusiasts.
  • Exploring Local Trails: The area offers scenic hiking and walking trails that showcase the natural beauty of Maine, ideal for outdoor lovers seeking adventure or tranquility.
  • Dining at Waterfront Restaurants: Savor fresh Maine cuisine at nearby waterfront eateries, providing a delightful culinary experience with picturesque views of the region’s waterways.
  • Golfing at Nearby Courses: Test your skills on local golf courses known for their well-maintained fairways and beautiful landscape, perfect for a leisurely day in the outdoors here.

Other Places to Stay in Winthrop, ME

Wilson Pond
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Annabessacook Lake
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Maranacook Lake
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Winthrop Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Outdoor Adventures: Take advantage of the region’s scenic trails and waterfront activities to fully enjoy your stay, ensuring you pack appropriate gear for outdoor exploration.
  • Book Early for Better Selection: Secure your preferred rental by owner in this area well in advance to access the best accommodations and avoid last-minute shortages.
  • Explore Local Dining Options: Sample the regional cuisine at nearby eateries or prepare meals in your rental to experience the local flavors authentically.
  • Utilize Nearby Amenities: Familiarize yourself with available amenities and services within the community to enhance comfort and convenience during your visit here.

Transportation Options

  • Winthrop Area Shuttle Services: Convenient for visitors seeking reliable transportation between rental properties and local points of interest within the region.
  • Local Taxi Companies: Offer on-demand rides around Winthrop, making it easy to explore the area without needing your own vehicle.
  • Regional Bus Lines: Connect here with nearby towns and cities, providing an affordable option for travel outside the destination.
  • Rental Car Agencies: Ideal if you prefer flexibility and independence during your stay in this scenic part of Maine.

Local Customs Options

  • Welcome Sign Tradition: You’ll notice a warm handshake and friendly greetings as locals often greet visitors with genuine hospitality in this welcoming region.
  • Community Events: Engaging in seasonal festivals and local gatherings offers an authentic way to connect with the area's rich cultural spirit.
  • Respect for Nature: The region’s residents take pride in maintaining the natural beauty, encouraging visitors to follow environmental guidelines during outdoor activities.
  • Historical Appreciation: Learning about local history through community storytelling and preserved landmarks enriches your experience here in this quaint destination.

Frequently Asked Questions About Winthrop Rentals by Owner

1. What are the top vacation rentals in Winthrop?

There are a lot of options in Winthrop. If you plan on staying in the Winthrop area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winthrop:

2. How many Rentbyowner vacation rentals are available in Winthrop?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 47 in the Winthrop area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winthrop. 

3. What is the cancellation policy for a rental by owner in Winthrop, Maine?

Cancellation policies vary depending on the individual listing. It is recommended to review the specific cancellation terms listed with each property or contact the owner directly for detailed information.

4. How do I ensure the rental by owner in Winthrop meets my needs?

You can check the property descriptions, amenities, and photos listed online, and reach out to the owner with any specific questions to confirm it aligns with your travel plans.

5. Are there any additional fees I should expect when booking a rental in this area?

Additional fees such as cleaning fees, service charges, or security deposits are typically specified in the listing details. Always review these before completing your reservation.

6. What should I do if I encounter issues during my stay?

Contact the property owner directly through the booking platform to report any problems. They are usually available to assist and ensure your stay remains comfortable.

7. Is it possible to modify or extend my booking in the region?

Modifications or extensions depend on the owner’s policies and availability. Contact the owner as early as possible to discuss your options.

More Rentals You May Like Near Winthrop

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10.0 (3 Reviews)
House
Cozy Keyes Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Winthrop Area