Find Vacation Rentals in Winter Harbor

We have 59 properties to choose from
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Popular Winter Harbor Vacation Rentals

Find the perfect Winter Harbor vacation rental

Resort Winter Harbor
from $147 per night
3 guests ∙ 1 bedroom

Resort

4.9
Outstanding(38 ratings)
Winter Harbor, Hancock County, Maine, United States
Vrbo
Details
House Winter Harbor
from $293 per night
House ∙ 6 guests ∙ 4 bedrooms

107 m² House

5.0
Outstanding(94 ratings)
Winter Harbor, Hancock County, Maine, United States
Vrbo
Details
Cottage Winter Harbor
from $291 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

134 m² Cottage

5.0
Outstanding(47 ratings)
Winter Harbor, Hancock County, Maine, United States
Vrbo
Details
Cottage Winter Harbor
from $274 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

121 m² Cottage

5.0
Outstanding(67 ratings)
Winter Harbor, Hancock County, Maine, United States
Vrbo
Details
House Winter Harbor
from $347 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(8 ratings)
Winter Harbor, Hancock County, Maine, United States
Vrbo
Details
House Winter Harbor
from $1,505 per night
8 guests ∙ 5 bedrooms

House

Winter Harbor, Hancock County, Maine, United States
Vrbo
Details
House Winter Harbor
from $608 per night
House ∙ 12 guests ∙ 3 bedrooms

222 m² House

5.0
Outstanding(3 ratings)
Winter Harbor, Hancock County, Maine, United States
HomeToGo
Details
Cottage Winter Harbor
from $359 per night
Cottage ∙ 7 guests ∙ 2 bedrooms

130 m² Cottage

5.0
Outstanding(1 rating)
Winter Harbor, Hancock County, Maine, United States
HomeToGo
Details
House Winter Harbor
from $135 per night
House ∙ 7 guests ∙ 4 bedrooms

116 m² House

4.6
Excellent(141 ratings)
Winter Harbor, Hancock County, Maine, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Winter Harbor
from $325 per night
House ∙ 2 guests ∙ 1 bedroom

70 m² House

5.0
Outstanding(84 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Vrbo
Details
House  Winter Harbor
from $354 per night
House ∙ 5 guests ∙ 3 bedrooms

92 m² House

4.9
Outstanding(107 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Vrbo
Details
House  Winter Harbor
from $623 per night
House ∙ 14 guests ∙ 8 bedrooms

251 m² House

5.0
Outstanding(26 ratings)
Winter Harbor, Hancock County, Maine, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Winter Harbor
from $258 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(3 ratings)
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
Vrbo
Details
Cabin  Winter Harbor
from $210 per night
2 guests ∙ 1 bedroom

Cabin

4.8
Outstanding(18 ratings)
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
Vrbo
Details
House  Winter Harbor
from $265 per night
House ∙ 5 guests ∙ 3 bedrooms

139 m² House

4.9
Outstanding(176 ratings)
Winter Harbor, Hancock County, Maine, United States
Pet-friendly
Vrbo
Details
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Vacation homes and rentals with a yard

House  Winter Harbor
from $1,111 per night
House ∙ 8 guests ∙ 4 bedrooms

223 m² House

Winter Harbor, Hancock County, Maine, United States
Yard
Vio.com
Details
House  Winter Harbor
from $231 per night
2 guests ∙ 1 bedroom

House

Winter Harbor, Hancock County, Maine, United States
Yard
Vio.com
Details
House  Winter Harbor
from $345 per night
House ∙ 6 guests ∙ 4 bedrooms

107 m² House

Winter Harbor, Hancock County, Maine, United States
Yard
Vio.com
Details
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Frequently Asked Questions

Can I find cheap vacation rentals in Winter Harbor?

In Winter Harbor, vacation rentals start at $134 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 59 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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