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Winter Harbor vacation rentals

We found 1,156 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:May 29 - Jun 5

Image gallery for Acadia Park 5 Min~Hot Tub~Theater~Game Room~Historic Home~Dogs welcome

Enjoy the beautiful backyard, boarding on Somes Brook, and wildlife sanctuary
10 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

Acadia Park 5 Min~Hot Tub~Theater~Game Room~Historic Home~Dogs welcome

Mount Desert

9% off
Price is $1,394
$9,756 for 7 nights
All fees included
Acadia Park 5 Min~Hot Tub~Theater~Game Room~Historic Home~Dogs welcome

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Find out more about Winter Harbor

Why visit Winter Harbor

  • Scenic Outdoor Adventures: Winter Harbor offers breathtaking landscapes perfect for hiking, kayaking, and exploring nature.
  • Charming Neighborhoods: Wander through inviting streets filled with friendly locals and unique coastal charm.
  • Beautiful Vacation Rentals: Choose from cozy cottages, private homes, and charming cabins for a perfect stay.
  • Family-Friendly Excursions: Enjoy activities suitable for all ages, from beach days to nature tours.
  • Peaceful Getaway: Experience a tranquil escape with stunning coastal views and serene surroundings.

Popular types of accommodation in Winter Harbor

If you're looking for the perfect place to stay in Winter Harbor, you're in luck. Our most popular accommodations include houses, cozy cottages, and charming cabins. Whether you seek a spacious rental in Maine for a family getaway or a quaint holiday cottage for a romantic retreat, we have something to suit every traveler's needs. Discover the ideal vacation rental in Winter Harbor and enjoy a memorable escape.

  • Houses: The top choice for visitors in Winter Harbor, these spacious homes offer a comfortable and private retreat for families and groups.
  • Cottages: Charming and cozy, cottages provide a delightful escape, perfect for couples or small families seeking a quaint getaway.
  • Cabins: Nestled in nature, cabins are ideal for those wanting a rustic experience while enjoying the serene surroundings of Winter Harbor.
  • Apartments: Convenient and versatile, apartments cater to travelers looking for a home-like atmosphere with easy access to local amenities.
  • Condos: Offering modern comforts and often great views, condos are a popular choice for those wanting a blend of luxury and convenience.**

Top attractions in and around Winter Harbor

Winter Harbor, Maine, is perfect for those seeking scenic outdoor adventures. Visitors can explore vibrant parks, charming neighborhoods, and picturesque capes, making it an ideal destination for cultural experiences and city exploration. Whether you're traveling solo, with family, or in a group, Winter Harbor offers a variety of attractions to suit all interests, ensuring a memorable vacation in this beautiful coastal area.

  • Village Green: A charming urban park located 6 miles from Winter Harbor, Village Green offers a family-friendly atmosphere with plenty of outdoor space to relax, play, and enjoy city vibes amidst nature.
  • Schoodic Peninsula: Nestled within Winter Harbor, Schoodic Peninsula boasts stunning scenery and beautiful beaches, perfect for leisurely walks, picnics, and taking in the breathtaking coastal views.
  • West Street Historic District: Just 6 miles from Winter Harbor, this vibrant town neighborhood features unique architecture and local shops, providing a quintessential city vibe for visitors to explore and enjoy.

Things to do recommended for couples

For a romantic getaway in Winter Harbor, consider a thrilling whale watching tour just 6 miles away, savor exquisite wines at Bartlett Maine Estate Winery nearby, or enjoy a fun round of mini-golf at Pirate's Cove Adventure Golf, 9 miles away. Each offers unique memories for couples.

Things to do recommended for families

Your family will love visiting the Sieur de Mont Nature Center, a serene recreation park just 7 miles from Winter Harbor, perfect for relaxation. Additionally, explore the Indian Point Trailhead, located 19 miles away, where you can enjoy the beauty of nature together.

Things to do recommended for groups

Groups visiting Winter Harbor can hike the scenic Shore Path for some outdoor adventure, enjoy a romantic evening at the Criterion Theater for a cultural experience, or play a round of golf at the Grindstone Neck Golf Course, perfect for sports enthusiasts and outdoor lovers alike.

*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

If you're traveling with a group, bringing your family or pets, or planning an extended stay, it's important to filter your options based on your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winter Harbor with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Harbor with young kids: Traveling with little ones can present some challenges. It’s important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, considering how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Winter Harbor: For many families, a vacation isn’t truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Harbor: If you're in search of vacation rentals offering discounts for extended 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Winter Harbor

Winter Harbor, Maine, offers a delightful blend of serene scenery and outdoor adventures. This charming city is perfect for a relaxing getaway, featuring beautiful vacation homes and stunning views of the coast. Nearby, you'll find family-friendly excursions and inviting beach areas, ideal for those seeking a peaceful escape. Experience the warmth of friendly locals while exploring the secluded beauty of this unique destination.

  • Bar Harbor: Located 6 miles from Winter Harbor, Bar Harbor is a vibrant city renowned for its stunning natural beauty and outdoor adventures. Visitors flock to this coastal gem for its hiking trails in Acadia National Park, breathtaking water sports, and bustling recreational areas. The town offers a delightful mix of scenic viewpoints, making it a perfect spot for photography enthusiasts. Don’t miss the chance to explore the local visitor center, which provides valuable insights into the area's rich history and ecology.
  • South Gouldsboro: Just 3 miles away from Winter Harbor, South Gouldsboro is a charming village that invites outdoor enthusiasts to experience its picturesque landscapes. This area is ideal for hiking, with numerous trails that wind through the lush scenery. Golf lovers will appreciate the local golf course, while the nearby national and state parks offer ample opportunities for exploration. South Gouldsboro’s close proximity to the coast allows for serene views and a peaceful atmosphere, making it a perfect retreat.
  • Prospect Harbor: Also located 3 miles from Winter Harbor, Prospect Harbor is a picturesque city that captivates visitors with its scenic vistas and outdoor activities. Here, you can enjoy hiking trails that showcase the area’s natural beauty or partake in exciting water sports along the harbor. The local national park and nearby cape enhance the coastal charm, providing ample opportunities for relaxation and exploration. Prospect Harbor is the perfect destination for those seeking adventure while soaking in the breathtaking scenery.

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 a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking 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

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the organizer definitely has its perks. When you enroll in our travel rewards program, One Key, you'll gain immediate access to exclusive member discounts and the opportunity to earn and redeem OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, and easily view and organize your travel plans. You can now find the properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To start using 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)
  • 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)
  • Bartlett Maine Estate Winery (6.1 mi / 9.8 km)
  • Kebo Valley Golf Club (7 mi / 11.2 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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