Winter Harbor vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winter Harbor
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Harbor vacation rentals
Other great vacation rentals in Winter Harbor
Cottage in Gouldsboro
4.89 out of 5 average rating, 123 reviewsShore Haven - Oceanfront Home in Corea by the Sea
Jan 16 – 23
Cottage in Gouldsboro
4.92 out of 5 average rating, 353 reviewsTimberframe Cottage on Organic Farm
Jun 6 – 13
Cottage in Hancock
4.99 out of 5 average rating, 317 reviewsLillebo
Sep 14 – 21
Cottage in Blue Hill
4.88 out of 5 average rating, 190 reviewsBrand new cottage close to downtown Blue Hill
Apr 4 – 11
Cottage in Lincolnville
4.91 out of 5 average rating, 330 reviewsEco-friendly studio - ocean views, close to beach
Jan 5 – 12
Cottage in Trenton
4.97 out of 5 average rating, 266 reviewsNEW Whitetail Cottage, Acadia National Park 7m
Nov 7 – 12
Cottage in Mount Desert
4.97 out of 5 average rating, 171 reviewsCraney "Tree" House near Acadia
Oct 22 – 29
Cottage in Lamoine
4.96 out of 5 average rating, 106 reviewsUp Back Cottage
May 11 – 18
Other great vacation rentals in Winter Harbor
Tiny home in Sullivan
4.99 out of 5 average rating, 151 reviewsNorth Star Tiny Mansion
Nov 3 – 10
Home in Gouldsboro
4.94 out of 5 average rating, 118 reviewsSchoodic Loft Cabin "The Roost" with Kayaks
Oct 25 – Nov 1
Apartment in Ellsworth
4.99 out of 5 average rating, 112 reviewsRoomy 2nd Fl 1-bedroom apt in downtown Ellsworth
Oct 9 – 16
Apartment in Hancock
4.98 out of 5 average rating, 196 reviewsFlower Farm Loft
Nov 13 – 20
Home in Winter Harbor
4.86 out of 5 average rating, 155 reviewsCozy Waterfront Cottage. Henry Cove, Winter Harbor
Dec 15 – 22
Cabin in Steuben
4.96 out of 5 average rating, 162 reviews*Stunning Views* Oceanfront Chalet
Oct 15 – 22
Farm stay in Franklin
4.91 out of 5 average rating, 505 reviewsBoreal Blueberry Bungalow - Organic Farm Getaway
Dec 19 – 26
Cabin in Winter Harbor
5.0 out of 5 average rating, 44 reviewsSchoodic Point Cabin
Feb 16 – 23
Quick stats about vacation rentals in Winter Harbor
Total rentals
90 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
2.3K reviews
Nightly prices starting at
$50 before taxes and fees
Frequently Asked Questions
What types of vacation rentals are available in Winter Harbor?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Winter Harbor. From over 40 house rentals to over 10 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there pet-friendly vacation rentals in Winter Harbor?
Four-legged friends are welcome in Winter Harbor. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winter Harbor?
Yes! Work meets play with ease at over 40 vacation rentals in Winter Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in cottage rentals in Winter Harbor?
Experience the best of Winter Harbor with our cottage rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Winter Harbor have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Winter Harbor have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Winter Harbor?
Winter Harbor has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winter Harbor have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
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