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Winter Harbor vacation rentals

We found 1,161 vacation rentals — enter your dates for availability

Discover a selection of 17 homes and other vacation rentals in Winter Harbor that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the amenities you expect for your stay, which might include air conditioning and a pool. No matter what you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Winter Harbor

Showing deals for:Jun 19 - Jun 26

Image gallery for Bar Harbor 5 bedroom 3 bath with hot tub and large backyard

Front of house
9.6 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Bar Harbor 5 bedroom 3 bath with hot tub and large backyard

Bar Harbor

9% off
Price is $783
$5,478 for 7 nights
All fees included
Bar Harbor 5 bedroom 3 bath with hot tub and large backyard

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Find out more about Winter Harbor

Why visit Winter Harbor

  • Scenic Outdoor Adventures: Enjoy the breathtaking natural beauty of Winter Harbor, with opportunities for hiking, biking, and exploring nearby Schoodic Woods Campground.
  • Charming Coastal Village: Experience the welcoming atmosphere of this friendly town, perfect for relaxing getaways.
  • Cultural Richness: Discover unique local attractions and immerse yourself in the vibrant culture of the area.
  • Family-Friendly Activities: Engage in a variety of excursions that cater to all ages, making it ideal for family vacations.
  • Cozy Accommodations: Choose from a range of vacation rentals, including charming cottages and private homes, to enhance your stay.

Popular types of accommodation in Winter Harbor

Planning a getaway to Winter Harbor? You're in for a treat. Explore a variety of vacation rentals, including houses, cozy cottages, and charming cabins. Whether you're seeking a winter rental or a vacation home for your family, Winter Harbor offers the perfect backdrop for your adventure. Discover the ideal place to unwind and create lasting memories in this picturesque destination.

  • Houses: These spacious and comfortable homes are the top choice for visitors, perfect for families or groups looking for a home-away-from-home experience.
  • Cottages: Quaint and charming, cottages offer a cozy atmosphere ideal for a peaceful getaway close to nature.
  • Cabins: Rustic cabins provide a unique retreat, perfect for those wanting to immerse themselves in the great outdoors.
  • Apartments: Convenient and modern, apartments are great for travelers seeking a home-like feel in the heart of Winter Harbor.
  • Condos: Offering a blend of comfort and amenities, condos are perfect for those wanting a more upscale vacation experience.**

Top attractions in and around Winter Harbor

Winter Harbor, Maine, offers a picturesque setting perfect for outdoor adventures and family experiences. Visitors can explore urban parks, charming neighborhoods, and stunning natural features. The area is rich in culture, making it an ideal destination for those seeking unique attractions. For a more extended stay, consider exploring vacation rentals in Winter Harbor to fully enjoy all the local sights and activities.

  • Schoodic Peninsula: A stunning coastal cape within Winter Harbor, Schoodic Peninsula offers beautiful beaches and breathtaking scenery. Enjoy hiking trails that wind through lush landscapes, providing incredible ocean views and opportunities for wildlife spotting.
  • Village Green: Located 6 miles away from Winter Harbor, this urban park is perfect for families. With spacious lawns, playgrounds, and picnic areas, it’s an ideal spot for outdoor activities and community events.
  • West Street Historic District: Also 6 miles from Winter Harbor, this charming neighborhood features historic architecture and a vibrant atmosphere. Stroll through the streets to admire the unique buildings and experience the local culture.

Things to do recommended for couples

For a romantic getaway in Winter Harbor, explore the breathtaking trails of Acadia National Park, enjoy a sunset picnic at Schoodic Point, or take a cozy boat ride to witness the stunning coastal views. Don't forget to savor fresh lobster at a local seafood restaurant for the perfect ending.

Things to do recommended for families

Families can explore the scenic Schoodic Peninsula, enjoy tide pooling at local beaches, or visit the Winter Harbor Lighthouse. Don't miss out on the nearby Acadia National Park for hiking and breathtaking views, making it a perfect spot for outdoor adventures together.

Things to do recommended for groups

Groups visiting Winter Harbor can enjoy a scenic boat tour of the beautiful Schoodic Peninsula, explore the picturesque Acadia National Park, and savor fresh seafood at local eateries. Don't miss the chance to participate in a guided lighthouse tour for breathtaking coastal views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winter Harbor

No matter if you're traveling with a group, your family, your pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winter Harbor with a group: Think about how many bedrooms you'll require, along with additional features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Winter Harbor with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winter Harbor: For many families, a vacation just isn't the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Winter Harbor: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Winter Harbor

Winter Harbor, Maine, offers a unique blend of serene coastal charm and outdoor adventure. This picturesque town is surrounded by stunning scenic views and is perfect for those seeking a relaxing getaway. Explore the nearby Schoodic Woods Campground for an immersive nature experience, or enjoy the welcoming atmosphere of this friendly coastal village. With family-friendly excursions and opportunities for adventure, Winter Harbor is a delightful destination for any traveler looking to unwind and explore.

  • Bar Harbor: Bar Harbor is a charming coastal city located 6 miles from Winter Harbor, known for its stunning outdoor experiences and breathtaking scenery. Travelers flock to Bar Harbor for adventures that include hiking trails and a variety of water sports. The nearby Acadia National Park offers an array of recreational areas perfect for exploring nature, while the local visitor center provides insights into the park’s unique ecosystems. Bar Harbor is an ideal base for those seeking both adventure and relaxation amidst picturesque landscapes.
  • South Gouldsboro: Just 3 miles from Winter Harbor, South Gouldsboro is a quaint village that captivates visitors with its serene outdoor settings and scenic beauty. Known for its recreational areas and golf courses, South Gouldsboro invites travelers to immerse themselves in the tranquility of nature. The proximity to national and state parks means you can easily explore lush hiking trails and enjoy the stunning coastal views. This village is perfect for those looking to unwind while experiencing the natural wonders of the Maine coastline.
  • Prospect Harbor: Located a mere 3 miles from Winter Harbor, Prospect Harbor is a delightful city that offers a blend of outdoor adventure and serene scenery. Visitors can engage in activities such as hiking and water sports, making the most of its beautiful landscapes. With easy access to national and state parks and the picturesque coastline, Prospect Harbor is an excellent spot for those who love nature. Enjoy the charm of local attractions while creating unforgettable memories in this coastal gem.

Best time to go to Winter Harbor

If you're planning a trip to Winter Harbor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.3°F (-4.3°C)Light RainMostly CloudyModerately LowSlightly Low
February25.2°F (-3.8°C)Light RainMostly CloudyAverageSlightly Low
March31.6°F (-0.2°C)Light RainMostly CloudyAverageSlightly Low
April41.9°F (5.5°C)Light RainMostly CloudyAverageAverage
May51.8°F (11.0°C)Light RainMostly SunnyAverageAverage
June59.4°F (15.2°C)Light RainMostly SunnyModerately HighSlightly High
July66.4°F (19.1°C)Light RainMostly SunnyModerately HighSlightly High
August66.2°F (19.0°C)Light RainMostly SunnyModerately HighSlightly High
September60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
October50.7°F (10.4°C)Light RainMostly SunnyAverageAverage
November39.7°F (4.3°C)Light RainMostly SunnyModerately LowAverage
December31.3°F (-0.4°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Keeping your travel dates flexible can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer certainly has its benefits. Become a part of our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient place to plan new trips, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Winter Harbor

Enjoy the musicals and other features of Winter Harbor. This city's seafood restaurants, golfing and boating draw many visitors. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Winter Harbor

Are you looking for things to do while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Winter Harbor a one-of-a-kind vacation spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Bar Harbor Whale Watching (6 mi / 9.7 km)
  • Kebo Valley Golf Club (7 mi / 11.2 km)
  • Heart of Acadia Loop (8.4 mi / 13.5 km)
  • Bubble Rock (9.7 mi / 15.7 km)
  • Wild Acadia Fun Park (16.2 mi / 26.1 km)
  • Grindstone Neck Golf Course (0.7 mi / 1.2 km)

Exploring the natural landscape of Winter Harbor

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Winter Harbor is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Acadia National Park (10.2 mi / 16.4 km)
  • Schoodic Peninsula (2.3 mi / 3.7 km)
  • Schoodic Point (4.4 mi / 7.1 km)
  • Shore Path (6 mi / 9.6 km)
  • Agamont Park (6 mi / 9.7 km)
  • Village Green (6 mi / 9.7 km)

Transportation options to and around Winter Harbor

The nearest airport is in Bar Harbor, ME (BHB-Hancock County - Bar Harbor), located 14.2 mi (22.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Winter Harbor, Maine, United States of America when booking a vacation rental?
When looking for the best area to stay in Winter Harbor, Maine, consider the charming neighborhood near the waterfront. This area offers a picturesque setting that captures the essence of coastal Maine. You'll find a variety of vacation rentals that cater to different preferences, from cozy cottages to larger family homes.

Being close to the water means you can easily access top attractions like the stunning Schoodic Peninsula, which is part of Acadia National Park and features breathtaking views, hiking trails, and opportunities for wildlife watching. The nearby Winter Harbor Marina is another highlight, where you can enjoy boating, kayaking, or simply relishing the scenic views of the harbor.
How much does it cost to rent a vacation home in Winter Harbor?
Prices for vacation rentals in Winter Harbor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Harbor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Harbor vacation house rentals?
You can find great discounts on house rentals in Winter Harbor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Winter Harbor?
For renting a beach house in Winter Harbor, travelers should explore the scenic coastline along the Schoodic Peninsula, which offers a tranquil atmosphere and breathtaking views of the Atlantic Ocean. Properties near the Winter Harbor Marina provide convenient access to both the water and local attractions. Many of these rentals come equipped with amenities such as spacious decks for enjoying the sea breeze, outdoor grills for barbecues, and fully stocked kitchens, superb for families and groups looking to enjoy a relaxing getaway by the beach.

Additionally, the nearby Acadia National Park's Schoodic section is a highlight, where visitors can find charming cottages and vacation homes located among the natural beauty of the park. These accommodations often feature cozy interiors, fireplaces, and easy access to hiking trails that lead to stunning coastal vistas. The area is also ideal for kayaking and wildlife watching, with some properties offering rental gear or information on local guided tours.

In the heart of Winter Harbor, travelers can discover quaint shops, restaurants, and galleries that reflect the local culture, making it easy to immerse themselves in the community during their stay.
What is the most popular type of vacation rental accomodation in Winter Harbor?
In Winter Harbor, vacation houses are the most popular type of rental, with about 16 available throughout the area. These properties typically offer spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces that allow guests to enjoy the scenic coastal views. Additionally, there are several cottages, apartments, campsites, and cabins available, providing a variety of options for different tastes and group sizes. Cottages and cabins often emphasize a cozy, rustic atmosphere, while apartments may offer more modern amenities.
Are there any family house rentals in Winter Harbor?
In Winter Harbor, Maine, there are some family-friendly rentals available, with about 15 options to choose from. This charming coastal town offers a variety of homes great for families looking to explore the beautiful surroundings. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and enjoy the fresh air.

Visitors will appreciate the close proximity to Acadia National Park, which offers stunning landscapes and a range of outdoor activities, including hiking and wildlife watching. Additionally, the nearby Schoodic Peninsula provides opportunities for scenic drives and picnicking by the water.
Can I find long-stay vacation rentals in Winter Harbor?
A long-stay vacation rental in Winter Harbor is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winter Harbor?
In Winter Harbor, travelers can find several pet-friendly house rentals that cater to both comfort and convenience. With around ten options available, visitors can choose from charming cottages and spacious homes that often come equipped with amenities such as full kitchens, outdoor spaces, and cozy living areas. This picturesque coastal town offers a serene atmosphere, making it an ideal getaway for families and groups traveling with pets.

The area is known for its natural beauty, with nearby Acadia National Park providing ample opportunities for outdoor activities. The park features pet-friendly trails and stunning coastal views, allowing furry companions to enjoy the great outdoors alongside their owners.
Are there any remote work vacation rentals in Winter Harbor?
In Winter Harbor, there are plenty of options for remote work vacation rentals, with around 23 properties available that cater to the needs of traveling professionals. These rentals typically feature essential amenities such as reliable Wi-Fi, dedicated workspaces with desks, and comfortable living areas conducive to productivity. Many properties also prioritize a business-friendly atmosphere, which can enhance the work-from-home experience.

Travelers can expect to find a range of accommodations, from cozy cottages to spacious homes, often equipped with full kitchens and outdoor spaces that allow for a refreshing break during the workday. The scenic beauty of Winter Harbor, with its proximity to Acadia National Park and stunning coastal views, provides an inspiring backdrop for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Harbor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter Harbor with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winter Harbor?
In Winter Harbor, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals while enjoying the scenic surroundings. Many properties feature decks or patios, great for relaxing outdoors and taking in the views. Cozy fireplaces are common, providing warmth and ambiance during cooler evenings. Onsite parking is also available, ensuring convenient access for travelers with vehicles. Additionally, most rentals come equipped with coffee and tea makers, making it easy for guests to enjoy their favorite beverages at any time.
When is the best time to visit Winter Harbor for a vacation rental?
July is the most popular month to visit Winter Harbor, Maine, making it an ideal time for those seeking a vibrant coastal experience. During the peak season from June to August, travelers flock to this charming town to enjoy the warm summer weather, which typically ranges from the mid-50s to mid-70s Fahrenheit. This period is superb for outdoor activities like hiking, kayaking, and exploring Acadia National Park, all while soaking in the picturesque views of the Atlantic coastline.

As you plan your visit, you'll find that the bustling atmosphere in July is complemented by a variety of local events and festivals that celebrate the region's rich maritime heritage. The lively community vibe enhances the experience, making it a great time for socializings and discovering local cuisine.

For travelers looking to save a bit on their vacation rental, consider planning your trip in November. While this month lies outside the peak season, it offers a unique opportunity to appreciate Winter Harbor's stunning natural beauty in a tranquil setting. The fall foliage creates a breathtaking backdrop, superb for scenic walks and photography, allowing you to experience the area's charm without the crowds.

Ultimately, the best time to visit Winter Harbor hinges on your preferences for either a lively summer adventure or a peaceful autumn retreat.
How early should I book a Winter Harbor vacation rental?
Book your Winter Harbor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winter Harbor, Maine, United States of America?
In Winter Harbor, visitors can enjoy a range of attractions that highlight the area's natural beauty and maritime culture. The Schoodic Peninsula, part of Acadia National Park, offers stunning coastal views, hiking trails, and opportunities for wildlife viewing, making it a must-visit for nature enthusiasts. Vacation rentals in this area often provide easy access to the park's scenic viewpoints and trails.

The charming harbor itself is a focal point for the community, where travelers can witness local fishermen at work and enjoy fresh seafood at nearby eateries. The nearby town of Gouldsboro also offers additional dining options and local shops, enriching the overall experience.

For those interested in maritime history, the Winter Harbor Lighthouse is a picturesque spot where visitors can take photographs and learn about the region's seafaring past.
Can I change or cancel my Winter Harbor home rental booking on Vrbo?
To find Winter Harbor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winter Harbor vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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