Photo by Ricky Batista

Winter Harbor vacation rentals

We found 1,091 vacation rentals — enter your dates for availability

Discover a selection of 16 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.
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Find out more about Winter Harbor

Find out more about Winter Harbor

Why visit Winter Harbor

  1. Outdoor Adventures: Enjoy hiking, biking, and exploring the stunning landscapes of nearby national parks and beautiful lakes.
  2. Charming Neighborhoods: Discover friendly, family-oriented communities perfect for leisurely strolls and local experiences.
  3. Scenic Coastline: Take in breathtaking ocean views and explore New England's picturesque coastline.
  4. Cozy Accommodations: Stay in charming oceanside cottages or private vacation homes with stunning water views.
  5. Local Cuisine: Indulge in delicious seafood and regional specialties at local eateries.

Popular types of accommodation in Winter Harbor

Planning a getaway to Winter Harbor? You're in for a treat! Explore a variety of popular vacation rentals, including charming oceanside cottages, houses, and cozy apartments. Whether you’re looking for stunning water views or the comfort of a whole home, Badger's Cottage welcomes you to unwind. Enjoy sought-after amenities and create unforgettable memories in this picturesque destination. Start your adventure now!

  • Cottages: Cottages are the top choice for vacation rentals in Winter Harbor, offering a cozy and charming atmosphere for your stay.
  • Houses: Ideal for families and groups, houses provide spacious and comfortable accommodations for a relaxing getaway.
  • Apartments: Apartments are a convenient option, perfect for couples or solo travelers seeking a home-like experience.
  • Cabins: Rustic and inviting, cabins offer a unique escape into nature while still providing modern amenities.
  • Condos: Condos combine comfort and convenience, often located near local attractions for an enjoyable vacation.**

Top attractions in Winter Harbor

Winter Harbor, Maine, is an ideal destination for outdoor and adventure enthusiasts, offering stunning scenery and a variety of attractions. Visitors can explore beautiful lakes, the nearby national park, and the local visitor center. Whether you're seeking a cultural experience, a beach getaway, or outdoor activities, Winter Harbor has something for everyone, making it a perfect spot for a memorable vacation.

  1. Acadia National Park: Located 10 miles from Winter Harbor, this national park offers breathtaking scenery and a plethora of outdoor activities. Explore its rugged coastline, hike scenic trails, and enjoy panoramic views of the Atlantic Ocean.
  2. Cadillac Mountain: Only 8 miles away, Cadillac Mountain is renowned for its stunning vistas and hiking opportunities. Experience the thrill of reaching the summit, which is one of the first places in the U.S. to see the sunrise.
  3. Village Green: Just 6 miles from Winter Harbor, this urban park is perfect for families. Enjoy its lush green spaces, walking paths, and a vibrant atmosphere that captures the essence of city life combined with outdoor enjoyment.

Things to do recommended for couples

For a romantic getaway in Winter Harbor, embark on a thrilling Bar Harbor Whale Watching tour just 6 miles away, savor fine wines at Bartlett Maine Estate Winery, and enjoy a fun-filled round of mini-golf at Pirate's Cove, located 9 miles from your stay. Perfect for couples!

Things to do recommended for families

Your family will enjoy the serene vibes at Sieur de Mont Nature Center, just 7 miles from Winter Harbor. For thrilling fun, head to Wild Acadia Fun Park, 16 miles away, or explore the scenic Indian Point Trailhead, located 19 miles from your base.

Things to do recommended for groups

In Winter Harbor, groups can hike the scenic Shore Path, play a round at Grindstone Neck Golf Course, or enjoy a show at the Criterion Theater, all while soaking in the local culture, outdoor adventures, and family-friendly entertainment options.

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

When traveling with a group, family, pets, or planning for an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Winter Harbor with a group: Think about how many bedrooms you require, as well as additional features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Winter Harbor with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winter Harbor: For many families, a vacation wouldn't be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels 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 month-long stays, 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Winter Harbor

Winter Harbor, Maine, offers a perfect blend of outdoor adventure and serene landscapes for an unforgettable vacation. Explore the charming neighborhoods, where family-friendly vibes meet relaxing excursions. Discover the beauty of New England's coastline, indulge in local cuisine, and soak in the secluded atmosphere. Whether you're seeking a winter getaway or summer escape, Winter Harbor and its surrounding areas promise a delightful experience filled with friendly locals and breathtaking scenery.

  • South Gouldsboro: Located only 3 miles from Winter Harbor, South Gouldsboro is a charming coastal community that offers a rich outdoor experience. This picturesque area is perfect for those seeking adventure, featuring an array of hiking trails and recreational areas that highlight the scenic beauty of Maine. Golf enthusiasts can also enjoy local courses amidst stunning landscapes. The proximity to a national state park and a captivating cape makes South Gouldsboro a must-visit for nature lovers and outdoor enthusiasts.
  • Prospect Harbor: Also situated just 3 miles from Winter Harbor, Prospect Harbor is renowned for its breathtaking scenery and vibrant outdoor activities. Visitors can engage in various water sports or explore the numerous hiking trails that wind through the area. With easy access to national parks and coastal attractions, this charming harbor town is ideal for adventure seekers looking to immerse themselves in Maine’s natural beauty while enjoying the tranquil coastal atmosphere.
  • Birch Harbor: Birch Harbor, a gem located 3 miles from Winter Harbor, invites travelers to explore its stunning landscapes and outdoor recreation options. This peaceful community is perfect for hiking and offers ample opportunities to connect with nature in its beautiful recreational areas. Birch Harbor is also neighboring national parks and picturesque capes, making it a great base for those looking to experience the breathtaking coastal environment of Maine while enjoying a variety of outdoor adventures.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January24.3°F (-4.3°C)Light RainMostly CloudyModerately LowAverage
February25.2°F (-3.8°C)Light RainMostly CloudyAverageModerately Low
March31.6°F (-0.2°C)Light RainMostly CloudyAverageModerately 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 HighModerately High
July66.4°F (19.1°C)Light RainMostly SunnyModerately HighModerately High
August66.2°F (19.0°C)Light RainMostly SunnyModerately HighModerately 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 LowModerately Low

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner certainly has its perks! When you join our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash™ on eligible reservations. Sign up today and begin reaping the benefits!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your travels. You can easily create new trips, resume planning from where you left off, or organize your existing plans. Your saved or booked properties will be neatly categorized under Potential, Upcoming, or Current Trips for your convenience. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • 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)
  • 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 most popular type of vacation rental accommodation in Winter Harbor?
Based on our data, cottages are the most sought-after type of vacation rental in Winter Harbor. But that goes without saying, everyone’s idea of an epic stay isn’t the same. Vrbo has vacation rentals of all sizes and shapes, and we’ll help you to find the perfect match.
How much does it cost to rent a vacation rental in Winter Harbor?
The average price for a vacation rental in Winter Harbor is based on a number of factors, like season, length of stay and property type. Whether you’d like a sprawling house with room for friends and family or an apartment perfect for just you and the kids, just add your travel dates to see stays with great value.
How much does it cost to rent a beach house in Winter Harbor?
The average price for a vacation home close to the beach in Winter Harbor depends on when you’re visiting the area and the style and size of property you’re looking for. You can easily and quickly find prices on Vrbo by entering your destination and preferred travel dates. Then make use of the filter tool to select the number of bedrooms and amenities that you prefer, such as a pool, air conditioning and WiFi.
Are there pet-friendly vacation rentals in Winter Harbor?
Yes. Pick from 20 vacation homes that roll out the welcome mat in Winter Harbor on Vrbo. Our furry kids also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to find a pad where your pup can lap up the fun.
What are popular rental amenities in Winter Harbor?
A nearby waterfront, a barbecue grill and an ocean view are rated the most popular rental amenities in Winter Harbor. Whether you’re taking a trip alone, with your sweetheart or a group of dear friends, Vrbo will help you find a vacation home that matches your tastes with all the extras you’re looking for.
Are there large group vacation rentals in Winter Harbor?
Yes, there are 13 vacation rentals in Winter Harbor that can host five or more guests. From family reunions to special occasions, these stays have ample space to hang out with the people that matter the most.
Are there vacation rentals in Winter Harbor that welcome kids?
Bring the whole group together for a memorable adventure in Winter Harbor at one of our 20 family-friendly vacation homes. Lots of these stays provide amenities that are great for getaways with the kids, like laundries, extra bedrooms and patios. Just check the “Properties good for families” filter and pick out your favorite.
What are the top attractions for families in Winter Harbor?
If you’re vacationing with the kids, make sure you put these family-friendly attractions in Winter Harbor on your to-do list:

  • Schoodic Peninsula
  • Grindstone Neck Golf Course

Are there one-bedroom vacation rentals in Winter Harbor?
Yes, Winter Harbor has four one-bedroom rentals on offer. Usually situated in popular spots thanks to their smaller size, a one-bedroom property is great if you’re traveling with your partner or a buddy. And with comforts such as kitchens and more privacy than a standard hotel, you’ll be able to kick back and relax while discovering this fabulous destination.
Can I find two-bedroom vacation rentals in Winter Harbor?
Gather your besties and enjoy total privacy and comfort in one of the five two-bedroom vacation properties Winter Harbor has to offer.
Are there vacation rentals with WiFi in Winter Harbor?
Winter Harbor has 12 vacation rentals with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to writing and sending emails, these Vrbo homes make it a cinch to go online.
How can I find vacation rentals with air conditioning in Winter Harbor?
Winter Harbor has seven vacation rentals where you can relax and recharge in air-conditioned comfort. To book a stay on Vrbo that offers this amenity, enter your desired travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Winter Harbor?
You’ll have to check with the Winter Harbor vacation home you’d like on Vrbo as age restrictions vary. However, it’s normally 16, 18 or 21.
How long can I rent a vacation rental in Winter Harbor for?
It’s really down to the Winter Harbor property. To view a list of options offering extended stays, simply type your travel dates and guest number into Vrbo’s search page. Enjoy having the entire property to yourself, along with the comforts of home like a fully-equipped kitchen and an outdoor space to play in. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Winter Harbor?
In Winter Harbor, you’ll find some fantastic bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it’s a weekend escape or a much longer stay, we’ve got plenty of options that’ll suit your style.

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