Winter Harbor, ME Cottage Rentals

Name: Winter Harbor
Address: Maine, US

Winter Harbor Cottage Rentals

Cottage

Lovely cottage on Acadia National Park's quiet Schoodic side. Pet friendly

10.0

Exceptional

(38 Reviews)

2 Bedrooms 1 Bath 5 Guests 1400 ft²

US $380/Night 7 Nights - US $2,657

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Historic Winter Harbor Cottage w/Waterfront Views

House

Historic Winter Harbor Cottage w/Waterfront Views

7.3

Very Good

(3 Reviews)

2 Bedrooms 2 Baths 7 Guests 1399.31 ft²

US $432/Night 7 Nights - US $3,024

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Cottage

The Boathouse feet from the ocean, modern farmhouse décor with spectacular views

10.0

Exceptional

(20 Reviews)

2 Bedrooms 1 Bath 2 Guests

US $364/Night 7 Nights - US $2,550

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Charming Waterfront Winter Harbor Cottage with Views!

House

Charming Waterfront Winter Harbor Cottage with Views!

4 Bedrooms 5 Baths 8 Guests 4004.17 ft²

US $463/Night 7 Nights - US $3,241

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Cottage

Historic Winter Harbor Cottage w/Waterfront Views

9.2

Exceptional

(32 Reviews)

2 Bedrooms 2 Baths 7 Guests 1400 ft²

US $448/Night 7 Nights - US $3,135

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Quaint and rustic cottage nestled on the shores of a small Maine village.

Highly Rated

Cottage

Quaint and rustic cottage nestled on the shores of a small Maine village.

10.0

Exceptional

(55 Reviews)

3 Bedrooms 2 Baths 6 Guests

US $718/Night 7 Nights - US $5,024

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Cottage

Down East Maine modern, well equipped cottage in heart of coastal Winter Harbor

10.0

Exceptional

(61 Reviews)

2 Bedrooms 2 Baths 5 Guests 1300 ft²

US $262/Night 7 Nights - US $1,831

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Cottage

Cozy Waterfront Cottage, Henry Cove. Winter Harbor

9.8

Exceptional

(13 Reviews)

3 Bedrooms 1 Bath 5 Guests 1000 ft²

US $404/Night 7 Nights - US $2,831

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Apartment

Coastal View 2 bedroom Apartment with Private Balcony in Winter Harbor, Maine

10.0

Exceptional

(11 Reviews)

2 Bedrooms 1 Bath 6 Guests

US $354/Night 7 Nights - US $2,480

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Prime Coastal Location! Large Family Villa

House

Prime Coastal Location! Large Family Villa

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 12 Guests 2400.35 ft²

US $600/Night 7 Nights - US $4,198

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Apartment

Coastal View 1 Bedroom Apartment with Private Balcony in Winter Harbor, Maine

10.0

Exceptional

(4 Reviews)

1 Bedroom 1 Bath 4 Guests

US $273/Night 7 Nights - US $1,908

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House

Charming Coastal House with Cozy Living Spaces and Outdoor Firepit

8.7

Fabulous

(3 Reviews)

3 Bedrooms 2 Baths 6 Guests 1603.82 ft²

US $492/Night 7 Nights - US $3,445

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More Top-Rated Cottage Rentals in Winter Harbor Area

Why Choose Rent By Owner for your Winter Harbor 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 Winter Harbor

When should you plan your Cottage Rentals stay?

To make the most of your stay in Winter Harbor, Maine, USA, consider planning your vacation during the region's quieter shoulder seasons when the area offers a peaceful and authentic experience, allowing you to enjoy the natural beauty and charm of these cottages at the ideal time.

Peak Season Highlights

Summer (June to August)

During the peak summer months, this destination experiences warm weather and long daylight hours, making it ideal for outdoor activities and enjoying the scenic coastal views.

Average Temperature Daytime: around 75°F to 85°F - Nighttime: about 55°F to 65°F

Fall (September to October)

Autumn brings vibrant foliage and pleasant weather, creating a picturesque setting that attracts visitors seeking a peaceful retreat in the region.

Average Temperature Daytime: approximately 60°F to 70°F - Nighttime: roughly 45°F to 55°F

Off-Season Highlights

Winter (December to February)

The winter months offer a serene atmosphere with cooler temperatures, perfect for those looking to enjoy quiet surroundings and cozy accommodations.

Average Temperature Daytime: around 25°F to 35°F - Nighttime: near 15°F to 25°F

Spring (March to May)

Spring signals a transition period with mild weather and blooming landscapes, providing an excellent opportunity to explore when crowds are minimal.

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

Weekly Weather Forecast for Winter Harbor

How to Book Your Winter Harbor 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 Winter Harbor

More Top-Rated Cottage Rentals in Winter Harbor 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 on a private deck or patio, perfect for taking in scenic views of the surrounding landscape.
Take advantage of spacious yards or gardens suited for outdoor activities and leisurely strolls.
Utilize dedicated parking areas that accommodate multiple vehicles for convenient access.
Make use of outdoor dining spaces ideal for enjoying meals amid fresh air and natural beauty.
Explore nearby hiking trails and nature walks directly accessible from your rental.
Benefit from easy access to waterfront or coastal areas, perfect for boating, fishing, or simply soaking in the vistas.

Top Attractions Around Winter Harbor

What attractions are nearby?

When staying in this destination, you can enjoy a variety of outdoor activities such as exploring scenic hiking trails, taking boat tours to discover local wildlife, and relaxing by the waterfront, all just minutes from your cozy cottages in Winter Harbor, Maine.

Family Activities

Winter Harbor Community Center Enjoy family-friendly activities and cultural events, perfect for engaging with the local community during your stay.
Schoodic Peninsula Explore scenic hiking trails and breathtaking coastal views that provide memorable outdoor adventures for all ages.
Downeast Sunrise Trail Bike or walk along this picturesque trail offering stunning vistas and a peaceful way to experience the region’s natural beauty.
Acadia National Park (nearby) Discover family-friendly nature programs, ranger-led tours, and easy hikes that make exploring the great outdoors accessible for everyone.

Adult Activities

Bird Watching: Experience the vibrant avian life by exploring the diverse bird habitats in the region, making it a perfect activity for nature enthusiasts staying here.
Hiking Adventures: Discover scenic trails along the coastline and through lush forests that offer breathtaking views, ideal for outdoor lovers seeking tranquility.
Sea Kayaking: Enjoy the calm waters from your cottage base by paddling along the shoreline, providing an intimate way to explore this coastal destination.
Local Art Exploration: Visit nearby galleries and art studios to immerse yourself in the creativity inspired by the area's natural beauty and vibrant community.

Other Places to Stay in Winter Harbor, ME

Winter Harbor Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead Book your cottages well in advance to secure the best options and ensure a smooth stay in this scenic region.
Explore Local Dining Take advantage of nearby eateries to enjoy authentic flavors that highlight the area's culinary charm.
Engage with Nature Utilize the region's outdoor opportunities, such as hiking or water activities, to fully immerse yourself in the natural beauty here.
Respect the Environment Follow sustainable practices during your visit to help preserve the pristine landscapes that make this destination special.

Transportation Options

Private Car Rentals: Renting a car offers you the flexibility to explore the scenic surroundings of this destination at your own pace, making it an ideal choice when staying in the area.
Taxis and Rideshare Services: Convenient for short trips around the region, these services provide reliable transportation options without the need for parking or driving yourself.
Local Shuttle Services: Some local providers offer shuttle routes that connect key points within the region, assisting visitors in reaching popular spots near their cottages with ease.
Public Transportation: Buses serve the area with routes that facilitate travel between nearby towns and attractions, allowing budget-friendly navigation during your stay.

Local Customs Options

Tradition of Lobstering Engaging in the region's lobster harvesting is a key local custom, reflecting the area's maritime heritage that you can experience firsthand during your stay.
Seafood Festivals Participating in seasonal seafood festivals showcases the community’s rich culinary traditions rooted in fresh, locally caught Maine seafood.
Shop Local Artisan Crafts Supporting local artisans by exploring craft markets allows you to embrace the area’s handcrafted goods and cultural expressions.
Boating and Maritime Activities Embracing the coastal lifestyle through boating or harbor tours provides an authentic connection to this destination’s seafaring customs.

Winter Harbor Cottage Rentals Frequently Asked Questions

1. What are the top Cottages in Winter Harbor?

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

2. How many Cottages are available in Winter Harbor?

Currently, the total number of properties listed by RBO in 2026 is over 8 in the Winter Harbor area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Winter Harbor. 

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

Cancellation policies vary depending on the specific listing and owner. It is recommended to review the cancellation terms outlined in the booking details or contact the host directly for clarification.

4. Are there any specific check-in and check-out times I should be aware of?

Check-in and check-out times are specified in each property’s details. Be sure to review these before confirming your reservation, and contact the host if you need any special arrangements.

5. Is there a minimum stay requirement at cottages in the region?

Minimum stay requirements can differ among properties. Please refer to the individual listing for this information or reach out to the property owner to confirm the length of your stay.

6. What amenities are typically available at these cottages?

Amenities vary by property but often include essentials such as Wi-Fi, kitchen facilities, and parking. For detailed information about what is included, review the listing details or contact the host directly.

7. How do I get assistance if I encounter issues during my stay?

Support is usually provided through the property owner or the platform’s customer service team. Contact the host via the messaging system or consult the support resources listed in your booking confirmation for prompt assistance.