Winter Harbor Holiday Homes from £86: Search Holiday Homes in Winter Harbor

A coastal town with a lighthouse, rocky shoreline, dense forest, and a clear blue sky.

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Our top choices for Winter Harbor holiday homes

A two-story house with a red door and a small attached structure with windows.

1. Water access house Acadia National Park Schoodic Point

Gouldsboro

Linette

includes taxes & fees

25 Oct - 26 Oct

A wooden deck with outdoor furniture, overlooking a body of water and a distant island.

2. Take in the breathtaking views at our popular oceanside cottage with large deck.

Gouldsboro

Corey B.

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a fireplace, white furniture, and a television mounted above it.

3. House Acadia at Gallagher`s Travels

Bar Harbor

Hunter H.

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with a stainless steel refrigerator, a built-in oven, and a gas stove.

4. The Crag: On the Acadia National Park Border - Deck, Fire Pit, Steps to Trails

Otter Creek

E O.

includes taxes & fees

29 Oct - 30 Oct

A two-story house with a front porch, a small garden, and two Adirondack chairs.

5. Blueberry Basecamp: 98ft to Acadia! Hike from Home, AC, Deck, Near Bar Harbor

Otter Creek

Rachel W.

includes taxes & fees

27 Oct - 28 Oct

A modern living room with a flat-screen TV, two leather armchairs, a white coffee table, and a black entertainment unit with storage baskets.

6. Wildwood Cottage at Gallagher`s Travels

Bar Harbor

Andrea C.

includes taxes & fees

8 Nov - 9 Nov

A single-story building with a covered porch, large windows, and a small outdoor seating area.

7. Tranquility by the Bay!

Steuben

Amy K.

includes taxes & fees

19 Oct - 20 Oct

8. Cozy Cottage Surrounded by Acadia National Park

Somesville

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio with Adirondack chairs, a fire pit, and a stone wall.

9. Carriage House - Crocker House Country Inn

Hancock Point

THERESA

includes taxes & fees

19 Oct - 20 Oct

A covered outdoor area with a wooden bench, a chair, and a wicker chair.

10. Cozy Milbridge Country Home

Milbridge

Gail C.

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a sloped ceiling, a bed with floral bedding, a window, and a view of trees.

11. Sun Shed Farm Stay

Milbridge

Matthew

includes taxes & fees

22 Oct - 23 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a central island with stools.

12. Beautiful Bar Harbor House

Bar Harbor

includes taxes & fees

19 Oct - 20 Oct

A living room with a wooden ceiling, a TV, a sofa, a coffee table, and a sail wheel decoration.

13. Quietside Hideaway @Acadia National Park, A/C, Seafood, Fire pit, sleeps 12

southwest harbor

Michael Q.

includes taxes & fees

1 Nov - 2 Nov

A cozy living room with a white sofa, a wooden coffee table, and a blue ottoman. There is a brick fireplace, a white dining table with chairs, and a kitchen area in the background.

14. Charming 2-bedroom house with WiFi, AC in Southwest Harbor

Southwest Harbor

"Really enjoyed our stay in Southwest Harbor, this 2 bedroom was perfect for our family. Liked the location of in Southwest Harbor, it wasn't as busy/crowded like parts of Bar Harbor. It was a perfect launching point for our adventures in Acadia. Kitchen had all the items needed to make us feel at home and communication with the owner was excellent. Would definitely stay here again next time we visit the area."

Todd S.

includes taxes & fees

25 Oct - 26 Oct

A sunlit room with a sofa, a table, and a chair.

15. Great Harbor Inn Clarks Quarters

Southwest Harbor

Ed L.

includes taxes & fees

1 Nov - 2 Nov

A cozy cabin with wicker furniture, a large window, and a wooden ceiling.

16. Mullein Hill Cottage: Escape Crowds to MDI’s Quiet, Historic Birthplace

Somesville

includes taxes & fees

21 Oct - 22 Oct

A deck with two white chairs and a stone base.

17. Acadia View Cottage: Peaceful, Pet Friendly, Fire Pit, Near Peaks and Echo Lake

Hall Quarry

"Great stay for a weekend hiking getaway with friends! The house was clean and nicely renovated. The beds were comfortable and the AC in all the upstairs bedrooms were great for cooling the house. The free snacks and coffee were a delightful surprise! There was easy car access to the main entrance to Acadia. The neighborhood was quiet and we enjoyed the evenings at the fire pit. It’s definitely a go-to place for our group the next time we are at Acadia!"

Tanishia C.

includes taxes & fees

19 Oct - 20 Oct

A clear beach with visible rocks and a forested shoreline.

18. Sugar Maple Farm near Acadia, Bar Harbor with FirePit, Large Deck

Lamoine

Hailey W.

includes taxes & fees

19 Oct - 20 Oct

Two white Adirondack chairs and a black grill on a grassy lawn with a house in the background.

19. Historical "MAINE" Home Minutes to Acadia National Park & Downtown Bar Harbor

Bar Harbor

"I'm the type of person who feels uneasy about leaving anything less than a five-star review, so giving a one-star rating is not something I do lightly. However, in this case, I believe it is fully warranted.I'll stick to the facts and set aside my personal emotions:- This cabin/cottage is part of a two-star motel.- The motel office, which is actively used, is part of the same house you a renting.- Another section of the house includes an entrance to basement that is also actively used during the...

Dmitry S.

includes taxes & fees

19 Oct - 20 Oct