Photo by Simmie Reagor

Winter Harbor holiday lettings

We found 1,163 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:5 Jun - 12 Jun

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

8% off
Price is £8,290
for 7 nights, 1 home
£1,184 per night
includes taxes & fees
Acadia Park 5 Min~Hot Tub~Theater~Game Room~Historic Home~Dogs welcome

Find spaces that suit your style

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)
  • 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 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 considering a holiday rental in Winter Harbor, Maine, the best area to stay in is near the picturesque harbour itself. This charming neighbourhood offers a serene atmosphere with stunning waterfront views that capture the essence of coastal Maine. Staying close to the harbour provides easy access to some of the area's top attractions, such as the breathtaking Acadia National Park, which is just a short drive away. This park is renowned for its dramatic landscapes, including rugged coastlines and lush woodlands, making it a favourite spot for outdoor enthusiasts.

In addition to the natural beauty, the local area boasts quaint shops and delightful eateries that serve fresh seafood and other regional specialities. You'll find a variety of holiday rental properties here, suiting different tastes and budgets, each providing a unique opportunity to immerse yourself in the local culture.
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, the scenic waterfront along the Frenchman Bay is an excellent choice. This area offers stunning views of the surrounding islands and easy access to sandy beaches, making it ideal for beach lovers. Properties here typically come with amenities such as spacious decks for enjoying the sunset, outdoor grills for barbecuing, and fully equipped kitchens that cater to families or groups. Many rentals also feature cosy living areas with fireplaces, superb for cooler evenings.

Additionally, the nearby Schoodic Peninsula provides a more secluded experience with its rugged coastline and natural beauty. Rentals in this vicinity often include features like private beach access, garden spaces for outdoor activities, and sometimes even kayaks or bicycles for exploring the stunning landscapes. The area is known for its tranquillity and proximity to nature, with opportunities for hiking and bird-watching in the Acadia National Park.
What is the most popular type of holiday rental accomodation in Winter Harbor?
In Winter Harbor, holiday houses are the most common type of holiday rental, with around 48 available throughout the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, fully furnished kitchens, and living areas that provide a comfortable home-away-from-home experience. Many holiday houses also come with outdoor spaces, great for enjoying the picturesque views of the surrounding nature.

Cottages are another popular option, with about 21 available, offering a charming and rustic atmosphere. They often include amenities such as kitchenettes and cosy living spaces, ideal for couples or small families looking for a quaint retreat.
Are there any family house rentals in Winter Harbor?
In Winter Harbor, Maine, there are numerous family-friendly house rentals available, with around 15 options to choose from. This charming coastal town offers a variety of accommodations suitable for families, often featuring spacious living areas, fully equipped kitchens ideal for preparing meals together, and outdoor spaces great for children to play. Many properties also include amenities such as Wi-Fi and laundry facilities, ensuring a convenient and comfortable stay.

Visitors can enjoy the stunning natural beauty of the area, as Winter Harbor is located near Acadia National Park, where families can explore hiking trails, picturesque landscapes, and scenic views. Additionally, the nearby Schoodic Peninsula offers opportunities for stunning coastal walks and wildlife viewing, making it a great spot for family outings.
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 several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. This charming coastal town is known for its scenic beauty and proximity to Acadia National Park, which offers ample opportunities for outdoor adventures with your furry friends.

Many of the holiday homes in Winter Harbor come equipped with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Some properties may include features like fire pits or private decks, great for relaxing after a day of exploration.

The nearby Schoodic Peninsula, part of Acadia National Park, is particularly top for its stunning coastal views and hiking trails, allowing for enjoyable walks with pets.
Are there any remote work holiday rentals in Winter Harbor?
In Winter Harbor, there are numerous remote work holiday rentals available, with around 69 options to choose from. This picturesque coastal town offers a tranquil environment that is conducive to productivity. Many of these properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated desks, and comfortable living spaces designed for both relaxation and work.

Visitors can enjoy the stunning views of the surrounding landscapes, with the nearby Acadia National Park providing opportunities for outdoor activities during breaks. The area features charming local eateries and shops, ensuring that everything you need is within reach. 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 holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties feature decks or patios where visitors can enjoy the serene surroundings. A fireplace is a common addition, providing warmth and a cosy atmosphere during the cooler months. Onsite parking is typically available, ensuring convenience for those travelling by car. Additionally, most rentals come with a coffee and tea maker for a comforting start to the day.
When is the best time to visit Winter Harbor for a holiday rental?
The most popular time to visit Winter Harbor is during the summer months of June to August, when the coastal charm truly comes alive. This peak season invites travellers seeking outdoor adventures, with opportunities for kayaking, hiking, and exploring Acadia National Park. The weather is typically warm, with temperatures ranging from 15 to 25 degrees Celsius, making it ideal for enjoying the stunning landscapes and vibrant local culture.

July stands out as the most popular month, with a lively option as families and outdoor enthusiasts gather to soak up the sun and partake in various activities. Visitors can explore the picturesque shores, indulge in fresh seafood, and attend local events that celebrate the region's heritage.

For those who prefer a quieter experience and are looking for better value, November is an excellent choice. While the weather turns cooler, this transitional month allows for peaceful walks along the coastline and an opportunity to witness the beautiful autumn colours without the crowds. It's a great time for photography and enjoying the serene beauty of nature.

Ultimately, the best time to book your holiday rental in Winter Harbor hinges on whether you're drawn to the vibrant energy of summer or the tranquil charm of the shoulder season.
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.
What are the top attractions in Winter Harbor?
In Winter Harbor, visitors can enjoy a variety of attractions that highlight the area's natural beauty and coastal charm. A major draw is the Schoodic Peninsula, part of Acadia National Park, which offers stunning views of the rugged coastline, hiking trails, and opportunities for birdwatching. The nearby Winter Harbor Lighthouse, a picturesque landmark, is worth a visit for its scenic surroundings.

The town itself features quaint shops and galleries that showcase local art and crafts, providing a taste of the community's culture. The local seafood restaurants offer fresh catches, giving visitors a chance to indulge in the region's culinary delights. For those interested in marine activities, the nearby waters are superb for kayaking and exploring the serene bays and coves.

Additionally, the annual Winter Harbor Lobster Festival draws crowds, celebrating the local fishing industry and offering a chance to experience the vibrant community spirit.
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 cabin or a beach house, 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 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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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