
Vacation rentals in Winter Harbor
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Top-rated vacation rentals in Winter Harbor
Guests agree: these stays 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
Winter Harbor cottage rentals

Ellie's Cottage—lovely, bright, and tasteful

Cozy Cottage on Frenchman Bay

Quiet lakefront cottage on Graham Lake

Meadow Point Cottage

Shore Haven - Oceanfront Home in Corea by the Sea

Fall Foliage 2025 Waterfront! Hi-Speed Wifi

Islesboro Boathouse

Cozy Seal Harbor Cottage
Other great vacation rentals in Winter Harbor

Bayview Cottage on the Atlantic

'Tugwassa' On Down East Jones Pond- poet's cottage

East of Acadia - A Spacious Waterfront Cottage

Perfect 3 bedroom New England home.

Wonderful Winter Harbor Retreat!

Seaswept Cottage

Downeast Oceanside Retreat on the Atlantic

Magnificent Oceanfront Modern, 8 Guests 4 Bedrooms
Quick stats about vacation rentals in Winter Harbor
Total rentals
110 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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 10 cottage rentals to over 60 house rentals, we've got you covered.
Are there pet-friendly vacation rentals in Winter Harbor?
Four-legged friends are welcome in Winter Harbor. Choose from more than 30 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 60 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 $260 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 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.
Do house rentals in Winter Harbor have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winter Harbor?
Winter Harbor has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Family-friendly rentals Winter Harbor
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- Rentals with a fireplace Winter Harbor
- Acadia National Park
- Northeast Harbour Golf Club
- Sandy Point Beach
- Bear Island Beach
- Sand Beach
- Kebo Valley Golf Club
- Spragues Beach
- Three Island Beach
- Wadsworth Cove Beach
- Narrow Place Beach
- Driftwood Beach
- North Point Beach
- Islesboro Town Beach
- Lighthouse Beach
- Hero Beach
- Hunters Beach
- Billys Shore
- Gilley Beach
- Pebble Beach
- Cellardoor Winery
- Bar Harbor Cellars
- Penobscot Valley Country Club
- Bartlett Maine Estate Winery and Distillery
- Great Beach