Find Vacation Rentals in Winter Harbor

We have 32 properties to choose from
Winter Harbor
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Winter Harbor
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Popular Winter Harbor Vacation Rentals

Find the perfect Winter Harbor vacation rental

House Winter Harbor
$466 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding (59 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
Details
Details
Cottage Winter Harbor
$279 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (46 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
Details
Details
House Winter Harbor
$480 per night
House ∙ 4 guests ∙ 3 bedrooms
4.9
Outstanding (131 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
Details
Details
House Winter Harbor
$961 per night
House ∙ 20 guests ∙ 7 bedrooms
5.0
Outstanding (20 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
Details
Details
House Winter Harbor
$248 per night
House ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding (163 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
Details
Details
Cottage Winter Harbor
$255 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (69 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
Details
Details
House Winter Harbor
$205 per night
House ∙ 7 guests ∙ 3 bedrooms
4.5
Excellent (145 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
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Details
Cabin Winter Harbor
$206 per night
Cabin ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (14 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
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Details
Cottage Winter Harbor
$284 per night
Cottage ∙ 2 guests ∙ 2 bedrooms
5.0
Outstanding (12 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
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Recommended Rentals With Pools

House  Winter Harbor
$241 per night
House ∙ 5 guests ∙ 3 bedrooms
4.9
Outstanding (80 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Details
Vrbo
Details
Details
House  Winter Harbor
$326 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (92 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Details
Vrbo
Details
Details
House  Winter Harbor
$670 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding (24 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Details
Vrbo
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Pet-Friendly Homes and Apartments

Cottage  Winter Harbor
$316 per night
Cottage ∙ 7 guests ∙ 2 bedrooms
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
Details
HomeToGo
Details
Details
House  Winter Harbor
$309 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (16 ratings)
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Winter Harbor
$139 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (50 ratings)
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
Details
Vrbo
Details
Details
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Vacation Homes With Terraces

House  Winter Harbor
$362 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (106 ratings)
Winter Harbor, Hancock County, Maine, United States
Balcony/Patio
Details
Vrbo
Details
Details
House  Winter Harbor
$216 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (22 ratings)
Winter Harbor, Hancock County, Maine, United States
Balcony/Patio
Details
Vrbo
Details
Details
Resort  Winter Harbor
$155 per night
Resort ∙ 3 guests ∙ 1 bedroom
4.8
Outstanding (40 ratings)
Winter Harbor, Hancock County, Maine, United States
Balcony/Patio
Details
Vrbo
Details
Details
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Frequently Asked Questions

Can I find cheap vacation rentals in Winter Harbor?

In Winter Harbor, vacation rentals start at $121 per night.

Are there any vacation rentals available to book in Winter Harbor?

Our large collection of vacation homes makes it easy to filter and compare 32 offers in Winter Harbor.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Winter Harbor

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Winter Harbor offers 86 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Winter Harbor start at an average price of $207 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 82 of Winter Harbor’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 2 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 71 vacation home rentals. Traveling with your dog or cat? Choose from 29 pet-friendly rentals in Winter Harbor that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 3 vacation rental sites in Winter Harbor where the top providers in that area are HomeAway, TripAdvisor, and Expedia. There are 61 HomeAway rentals, 19 TripAdvisor short term rentals and 6 Expedia vacation rentals.

Popular Day Trips Near Winter Harbor

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