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
4.92 out of 5 average rating, 353 reviewsTimberframe Cottage on Organic Farm
Jun 8 – 15
Cottage in Gouldsboro
4.89 out of 5 average rating, 123 reviewsShore Haven - Oceanfront Home in Corea by the Sea
Apr 22 – 29
Cottage in Waltham
4.95 out of 5 average rating, 675 reviewsQuiet lakefront cottage on Graham Lake
Jan 24 – 31
Cottage in Hancock
4.99 out of 5 average rating, 317 reviewsLillebo
Sep 25 – Oct 2
Cottage in Blue Hill
4.88 out of 5 average rating, 190 reviewsBrand new cottage close to downtown Blue Hill
Mar 7 – 14
Cottage in Lincolnville
4.91 out of 5 average rating, 332 reviewsEco-friendly studio - ocean views, close to beach
Nov 21 – 28
Cottage in Mount Desert
4.97 out of 5 average rating, 171 reviewsCraney "Tree" House near Acadia
Nov 3 – 10
Cottage in Hampden
4.98 out of 5 average rating, 229 reviewsMaineStay Cottage #5 Full Kitchen Hampden/Bangor
Nov 27 – Dec 4
Other great vacation rentals in Winter Harbor
Apartment in Bar Harbor
4.99 out of 5 average rating, 141 reviewsHuckleberry Suite - Intown Bar Harbor
Mar 31 – Apr 7
Tiny home in Sullivan
4.99 out of 5 average rating, 151 reviewsNorth Star Tiny Mansion
Dec 24 – 31
Apartment in Hancock
4.98 out of 5 average rating, 197 reviewsFlower Farm Loft
Mar 27 – Apr 3
Cabin in Steuben
4.96 out of 5 average rating, 163 reviews*Stunning Views* Oceanfront Chalet
Dec 10 – 17
Apartment in Ellsworth
4.99 out of 5 average rating, 112 reviewsRoomy 2nd Fl 1-bedroom apt in downtown Ellsworth
Oct 8 – 15
Cabin in Eastbrook
4.95 out of 5 average rating, 184 reviewsHemlock Cabin.
Jan 6 – 13
Apartment in Southwest Harbor
4.94 out of 5 average rating, 119 reviewsThe Snuggery - Downtown Southwest Harbor - Acadia
Jan 30 – Feb 6
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
ﺩ.ﺇ184 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.
Destinations to explore
- Bar Harbor Vacation rentals
- Bangor Vacation rentals
- Acadia National Park Pond Vacation rentals
- St. Andrews Vacation rentals
- Camden Vacation rentals
- Grand Manan Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Halifax Vacation rentals
- Moncton Vacation rentals
- Waterfront rentals Winter Harbor
- Rentals with outdoor seating Winter Harbor
- Monthly Rentals Winter Harbor
- House rentals Winter Harbor
- Rentals with a patio Winter Harbor
- Rentals with a fire pit Winter Harbor
- Rentals with a washer and dryer Winter Harbor
- Family-friendly rentals Winter Harbor
- Pet-friendly rentals Winter Harbor
- Rentals with a fireplace Winter Harbor
- Rentals with beach access Winter Harbor
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom