Photo by Ricky Batista

Winter Harbor holiday lettings

We found 994 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 14 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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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)
  • 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 mi / 6.4 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 most popular type of holiday rental accommodation in Winter Harbour?

Houses are the most popular type of holiday rental in Winter Harbour, according to our data. Even if you have a different idea about what you want, Vrbo has properties in a variety of shapes and sizes. Look through our options to find your ideal fit.

How much does it cost to rent a holiday rental in Winter Harbour?

Property type, length of stay and time of year are some of the things that can influence the price of a holiday home. Simply add your dates of travel to find your ideal fit. From homey country cottages to plush villas, all Vrbo holiday rentals offer amazing value.

How much does it cost to rent a beach house in Winter Harbour?

When you travel and the size and style of the property will influence the cost of your beachside escape. Type in your Winter Harbour travel dates to see your options on Vrbo. Can't live without a hot tub? Use the filters to select the amenities and features you need.

Are there pet-friendly holiday rentals in Winter Harbour?

You're in luck. There are. Choose from 18 stays that roll out the welcome mat in Winter Harbour on Vrbo. Our furry best friends need a getaway too, so simply use our search function for pet-friendly holiday rentals to find a perfect pad where your puppy dog can lap up the good times.

What are popular rental amenities in Winter Harbour?

An ocean view, a barbecue grill and a beach view top the list of most popular rental amenities in Winter Harbour. Whether you're planning to travel by yourself, with a partner or as a family group, Vrbo can help you find a holiday rental that suits your tastes with all the features you're looking for.

Are there large group holiday rentals in Winter Harbour?

Take your pick of 12 Vrbo holiday homes in Winter Harbour that can host five or more people. You'll get all the room and privacy you need to relax with your favourite people — and no one else.

Are there holiday rentals in Winter Harbour that welcome kids?

Winter Harbour has 18 family-friendly holiday rentals to pick from. And tracking down a stay that welcomes little ones is simple with our "Properties good for families" filter. As well as having the whole place to yourselves, you'll also enjoy access to perks and conveniences such as dining rooms, private pools and yards.

What are the top attractions for families in Winter Harbour?

Keep the kids entertained at these top family-friendly attractions in Winter Harbour:

  • Bar Harbour Whale Watching
  • Bar Harbour Historical Society
  • College of the Atlantic Natural History Museum

Are there one-bedroom holiday rentals in Winter Harbour?

Yes, Winter Harbour has two one-bedroom rentals available. Often located in popular spots due to their smaller size, a one-bedroom holiday rental is perfect if you're getting away with a pal or your partner. And with plenty of home comforts like wireless internet and more privacy than a standard hotel, you'll be able to kick back and relax while discovering this exciting destination.

Can I find two-bedroom holiday rentals in Winter Harbour?

Gather your besties and enjoy peace, privacy and comfort in one of the five two-bedroom holiday properties Winter Harbour has to offer.

Are there holiday rentals with WiFi in Winter Harbour?

Whether you want to stay in touch with world events, send some emails or surf social media, there are 10 holiday homes with WiFi in Winter Harbour. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How can I find holiday rentals with air conditioning in Winter Harbour?

There are six holiday rentals with air conditioning in Winter Harbour providing that gentle, cool breeze and extra bit of comfort. Just enter your preferred dates of travel and then take advantage of our filter tool to help you book properties with air conditioning.

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