Photo by Ricky Batista

Winter Harbor holiday lettings

We found 1,149 holiday rentals — enter your dates for availability

Discover a selection of 17 homes and other holiday rentals in Winter Harbor that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Winter Harbor

Showing deals for:9 Jan - 16 Jan
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Find out more about Winter Harbor

Find out more about Winter Harbor

Why visit Winter Harbor

  • Scenic Outdoor Adventures: Explore the breathtaking landscapes and natural beauty of Winter Harbor and nearby Bar Harbor, perfect for hiking and coastal walks.
  • Charming Neighbourhoods: Stroll through quaint streets filled with local shops and friendly residents, showcasing the unique character of the area.
  • Waterfront Activities: Enjoy a variety of water-based excursions, from kayaking to relaxing by the shore, offering fun for all ages.
  • Comfortable Accommodations: Choose from a delightful selection of private homes, cottages, and cabins for a cosy stay.
  • Cultural Experiences: Immerse yourself in local culture and events that highlight the rich heritage of Winter Harbor.

Popular types of accommodation in Winter Harbor

If you're considering a getaway to Winter Harbor, you'll find a delightful selection of accommodations to suit your needs. Our most popular options include houses, charming cottages, and cosy cabins. Whether you're searching for Winter Harbor hotels, the best inns, or unique vacation rentals, we provide transparent information to ensure a seamless booking experience. Enjoy your stay with reassurance and savings at the heart of your adventure in this picturesque destination.

  • Houses: The top choice for visitors in Winter Harbor, these homes offer spacious and comfortable stays ideal for families and groups.
  • Cottages: Quaint and charming, cottages provide a perfect retreat with a homely feel, often nestled in picturesque settings.
  • Cabins: Rustic and inviting, cabins offer a cosy escape, perfect for those wanting to immerse themselves in nature.
  • Apartments: Convenient and versatile, apartments are great for couples or solo travellers seeking a little independence.
  • Condos: Combining luxury with convenience, condos provide modern amenities and often stunning views of the surrounding area.**

Top attractions in and around Winter Harbor

Winter Harbor, Maine, is an ideal destination for those seeking scenic outdoor adventures and cultural experiences. Visitors can explore captivating urban parks, charming neighbourhoods, and stunning capes. With a variety of attractions nearby, including the popular Bar Harbor, Winter Harbor offers something for everyone, whether you're travelling with family or looking for unique experiences. Don’t miss the chance to discover local highlights and RV sites in the area to enhance your stay.

  • Village Green: A charming urban park located 3.7km from Winter Harbor, Village Green offers a delightful outdoor experience, perfect for families. Enjoy leisurely strolls amidst lush greenery, playgrounds for children, and the vibrant atmosphere of the city.
  • Schoodic Peninsula: Nestled within Winter Harbor, Schoodic Peninsula showcases stunning coastal scenery and tranquil beaches. It's an ideal spot for nature enthusiasts, offering picturesque views and opportunities for exploration along the rugged shoreline.
  • West Street Historic District: Situated 3.7km from Winter Harbor, this historic neighbourhood is rich in character, featuring charming architecture and a vibrant community vibe. Wander the streets to soak in the local history and enjoy quaint shops and cafes.

Things to do recommended for couples

For a romantic getaway in Winter Harbor, consider whale watching with Bar Harbor Whale Watching for an adventurous day on the water. Alternatively, enjoy a delightful afternoon at Bartlett Maine Estate Winery, perfect for sipping wine together. Cap off your trip with a fun round at Pirate's Cove Adventure Golf.

Things to do recommended for families

During your family holiday in Winter Harbor, explore the Sieur de Mont Nature Center, just 4.3km away, for a serene outdoor experience. Additionally, the Indian Point Trailhead, located 11.8km from Winter Harbor, offers a lovely trail for a relaxing family hike.

Things to do recommended for groups

Groups visiting Winter Harbor can embark on the scenic Shore Path for a delightful hike, immerse themselves in culture at the Criterion Theater, and enjoy a round of golf at the Grindstone Neck Golf Course, all while soaking in the area's natural beauty and vibrant atmosphere.

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

If you're planning a trip with friends, family, pets, or extended stays, it's important to refine your search according to your key priorities. Here are some helpful tips for booking with Vrbo.

  • Traveling to Winter Harbor with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Winter Harbor with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can be beneficial.
  • Taking your pets with you to Winter Harbor: For many, a family holiday wouldn’t feel complete without their furry companion. If you can relate, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer 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 holiday rentals that offer great deals for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Additionally, you might want to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Winter Harbor

Winter Harbor, Maine, offers a delightful blend of scenic beauty and outdoor adventure for every traveller. Just a stone's throw away, Bar Harbor captivates with its lovely waterfront and family-friendly atmosphere. Enjoy warm weather excursions, where friendly locals ensure a welcoming experience. Whether you seek tranquil moments by the water or thrilling adventures, Winter Harbor and its surrounding regions promise a memorable holiday filled with exploration and relaxation.

  • Prospect Harbor: Located a mere 1.9km from Winter Harbor, Prospect Harbor is a picturesque city that beckons outdoor enthusiasts and adventure seekers. Visitors are drawn to its stunning scenery and abundant recreational opportunities, with hiking trails and water sports being particularly popular. The nearby national state park and cape provide a perfect backdrop for exploring the natural beauty of the area. Whether you're kayaking along the coast or hiking through lush trails, Prospect Harbor offers a delightful escape into nature.
  • South Gouldsboro: This charming village, situated 1.9km from Winter Harbor, is a treasure trove for those who appreciate the great outdoors. South Gouldsboro is famed for its breathtaking landscapes and exhilarating adventures. With easy access to hiking trails and recreational areas, it’s an ideal spot for family outings or solo adventures. The proximity to national parks and scenic capes enhances the appeal, making it a perfect destination for those looking to immerse themselves in Maine’s natural splendour.
  • Birch Harbor: Just 1.9km from Winter Harbor, Birch Harbor is another delightful city that captivates visitors with its scenic vistas and outdoor activities. Known for its welcoming atmosphere, the area is perfect for hiking and enjoying recreational pursuits. Birch Harbor’s close-knit community vibe and proximity to national parks and stunning coastal landscapes make it an excellent base for exploration. Whether you're hiking through the woods or relaxing by the waterfront, Birch Harbor promises a memorable experience for all who visit.

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 journey? It may be beneficial to maintain some flexibility with your travel dates, as prices can vary considerably. Additionally, opting for a longer stay often results in significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up from where you last paused, or review and arrange your travel itinerary. You can easily access properties you've previously saved or booked, now categorised under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/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 holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winter Harbor

Are you hoping to discover things to do in the city? Venture out of your cosy holiday rental and experience everything that makes Winter Harbor a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bar Harbor Whale Watching (6 mi / 9.7 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)
  • Bartlett Maine Estate Winery (6.1 mi / 9.8 km)

Exploring the natural landscape of Winter Harbor

Whether you're an outdoor enthusiast or just want to take in the scenery, Winter Harbor is a great place to get outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport 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 centre.

Frequently asked questions

What is the best area to stay in Winter Harbor when booking a holiday rental?
When planning a holiday rental in Winter Harbor, Maine, one of the most appealing areas to consider is the vicinity near the Schoodic Peninsula. This picturesque neighbourhood offers a serene coastal atmosphere and direct access to the stunning landscapes of Acadia National Park's less-travelled section. The Schoodic Peninsula is renowned for its breathtaking ocean views, rocky shorelines, and peaceful hiking trails, making it an ideal location for nature enthusiasts.

In this area, visitors can enjoy attractions such as the Schoodic Institute, which often hosts educational programmes and events, allowing guests to immerse themselves in the local ecology and community. Additionally, the nearby Schoodic Point is a must-visit for its dramatic ocean vistas and opportunities for tide pooling and bird watching.
How much does it cost to rent a holiday home in Winter Harbor?
Prices for holiday 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 holiday 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, Maine, the picturesque area along the eastern shore of the Schoodic Peninsula is ideal. This region offers stunning views of the Atlantic, and properties here often come with amenities such as outdoor decks for enjoying the fresh sea air, spacious living areas, and fully equipped kitchens, great for families and groups looking to unwind by the coast.

Nearby, Acadia National Park's Schoodic section provides a beautiful backdrop for your stay, with hiking trails and scenic vistas just a short drive away. Many holiday rentals in this area feature easy access to both the beach and the park, with some properties including outdoor fire pits and picnic areas, enhancing the experience of coastal living.
What is the most popular type of holiday rental accomodation in Winter Harbor?
In Winter Harbor, holiday houses are the most popular type of rental accommodation, with around 16 available in the area. These houses are typically located in serene neighbourhoods, offering a peaceful retreat close to the beautiful coastline and Acadia National Park. Most holiday houses come equipped with essential amenities, including fully stocked kitchens, spacious living areas, and outdoor spaces for relaxing or enjoying meals al fresco.
Are there any family house rentals in Winter Harbor?
In Winter Harbor, Maine, there are a variety of family-friendly house rentals available, with around 16 options to choose from. This charming coastal town is superb for families looking to enjoy a peaceful getaway. Many properties provide spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play.
Can I find long-stay holiday rentals in Winter Harbor?
A long-stay holiday rental in Winter Harbor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winter Harbor?
In Winter Harbor, there are a number of pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties offer charming coastal accommodations with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.
Are there any remote work holiday rentals in Winter Harbor?
In Winter Harbor, Maine, there are numerous remote work holiday rentals available, with around 24 options for those seeking a productive getaway. The area is known for its stunning coastal scenery and proximity to Acadia National Park, making it an attractive destination for both work and leisure. Many of the rentals are equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a conducive environment for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Harbor holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winter Harbor with parking available—perfect for families or travellers 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 well-equipped kitchens, which are essential for guests looking to prepare their own meals during their stay. Most holiday rentals come with microwaves, cookware, dishware, and utensils, making it convenient for travellers to dine in. Additionally, refrigerators are commonly available, ensuring that guests can store their groceries and beverages.
When is the best time to visit Winter Harbor for a holiday rental?
The peak season for visiting Winter Harbor is during the summer months, specifically from June to August. This is when the area comes alive with travellers seeking to enjoy the beautiful coastal scenery, explore Acadia National Park, and partake in a variety of outdoor activities such as hiking, kayaking, and birdwatching. With temperatures typically ranging from the mid-teens to low 20s Celsius, the summer months offer a comfortable climate for both relaxation and adventure.

July stands out as the most popular month, welcoming visitors who are eager to soak up the sun and engage with the vibrant local culture. Whether you're wandering along the picturesque waterfront, indulging in fresh seafood, or participating in community events, there's an infectious energy that enhances your holiday experience.

For those looking for a more budget-friendly option, consider planning your visit in November. This quieter month allows you to appreciate the serene beauty of Winter Harbor without the hustle and bustle of peak season. Crisp autumn air and stunning views create a great backdrop for leisurely walks and enjoying the tranquility of the coast.
How early should I book a Winter Harbor holiday rental?
Book your Winter Harbor holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winter Harbor home rental booking on Vrbo?
To find Winter Harbor holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winter Harbor holiday 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.

More holiday ideas

More holiday ideas