Find Vacation Rentals in Winter Harbor

We have 34 properties to choose from
Winter Harbor
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Popular Winter Harbor Vacation Rentals

Find the perfect Winter Harbor vacation rental

House Winter Harbor
$229 per night
House ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (140 ratings)
Winter Harbor, Hancock County, Maine, United States
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Vrbo
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House Winter Harbor
$237 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (76 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
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House Winter Harbor
$385 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (101 ratings)
Winter Harbor, Hancock County, Maine, United States
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Vrbo
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Cottage Winter Harbor
$280 per night
Cottage ∙ 2 guests ∙ 2 bedrooms
Winter Harbor, Hancock County, Maine, United States
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Vrbo
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Cottage Winter Harbor
$249 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (53 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
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House Winter Harbor
$181 per night
House ∙ 7 guests ∙ 3 bedrooms
4.6
"Outstanding" (140 ratings)
Winter Harbor, Hancock County, Maine, United States
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Vrbo
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House Winter Harbor
$353 per night
House ∙ 6 guests ∙ 3 bedrooms
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
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House Winter Harbor
$484 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
"Excellent" (52 ratings)
Winter Harbor, Hancock County, Maine, United States
Details
Vrbo
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House Winter Harbor
$310 per night
House ∙ 5 guests ∙ 3 bedrooms
Winter Harbor, Hancock County, Maine, United States
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Vrbo
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Recommended Rentals With Pools

Apartment Pool Winter Harbor
$124 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.9
"Excellent" (150 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Details
Vrbo
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House Pool Winter Harbor
$210 per night
House ∙ 3 guests ∙ 1 bedroom
5.0
"Excellent" (81 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Details
Vrbo
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House Pool Winter Harbor
$227 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (109 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

Cottage Pet-friendly Winter Harbor
$309 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (26 ratings)
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
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Vrbo
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Cabin Pet-friendly Winter Harbor
$170 per night
Cabin ∙ 2 guests ∙ 1 bedroom
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
Details
Vrbo
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House Pet-friendly Winter Harbor
$3,561 per night
House ∙ 24 guests ∙ 9 bedrooms
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
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Vrbo
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Vacation homes and rentals with a yard

Cottage Yard Winter Harbor
$138 per night
Cottage ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (110 ratings)
Winter Harbor, Hancock County, Maine, United States
Yard
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Vrbo
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Farmhouse Yard Winter Harbor
$271 per night
Farmhouse ∙ 4 guests ∙ 3 bedrooms
4.8
"Excellent" (61 ratings)
Winter Harbor, Hancock County, Maine, United States
Yard
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Vrbo
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Cottage Yard Winter Harbor
$131 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (81 ratings)
Winter Harbor, Hancock County, Maine, United States
Yard
Details
Vrbo
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Details
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Frequently Asked Questions

Can I find cheap vacation rentals in Winter Harbor?

In Winter Harbor, vacation rentals start at $122 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 34 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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