Winter Harbor Holiday Homes from £84: 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

3 Sept - 4 Sept

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

2. House Acadia at Gallagher`s Travels

Bar Harbor

Hunter H.

includes taxes & fees

3 Sept - 4 Sept

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

3. Tranquility by the Bay!

Steuben

Amy K.

includes taxes & fees

11 Sept - 12 Sept

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

4. Sun Shed Farm Stay

Milbridge

Matthew

includes taxes & fees

9 Sept - 10 Sept

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

5. Cozy Milbridge Country Home

Milbridge

Gene B.

includes taxes & fees

3 Sept - 4 Sept

A two-story building with a wooden front porch and large windows.

6. The Colonels Suites

Northeast Harbor

includes taxes & fees

20 Sept - 21 Sept

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

7. Wildwood Cottage at Gallagher`s Travels

Bar Harbor

Andrea C.

includes taxes & fees

8 Sept - 9 Sept

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

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

Otter Creek

John S.

includes taxes & fees

23 Sept - 24 Sept

A deck with two white chairs and a stone base.

9. 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

3 Sept - 4 Sept

A lakeside setting with a fire pit and wooden chairs arranged around it.

10. Have an unforgettable getaway at a family sized beach house with private beach!

Steuben

Anonymous traveller

includes taxes & fees

18 Sept - 19 Sept

A beach with a person standing, trees in the foreground, and a calm body of water with boats.

11. Booking now for summer & fall 2026-explore Acadia, Bar Harbor, Downeast Maine

Franklin

Staci D.

includes taxes & fees

27 Sept - 28 Sept

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

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

Somesville

includes taxes & fees

8 Sept - 9 Sept

A modern kitchen with white cabinetry, a central island with bar stools, a microwave, and a coffee machine.

13. Acadia Retreat- 3 bedroom, 2 bath on two private serene acres

Lamoine

Eddie G.

includes taxes & fees

7 Sept - 8 Sept

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

14. Beautiful Bar Harbor House

Bar Harbor

includes taxes & fees

3 Sept - 4 Sept

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.

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

Southwest Harbor

Karren Y.

includes taxes & fees

30 Sept - 1 Oct

A wooden cabin interior with a loft bedroom, a living area with a sofa and chairs, and a dining table.

16. Lumberjack Cottages

Franklin

includes taxes & fees

3 Sept - 4 Sept

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a bar area with leather stools.

17. Beautiful Bar Harbor House

Bar Harbor

"The location was perfect for our goals of hiking and visiting the park and spending time in Bar Harbor. As a new rental, the only major concern occurred upon arrival when we unexpectedly found a staffer in the home. She explained she was a worker in the neighboring rentals and we learned that all the staff had access through two entrances shown in attached photo below: the laundry facility and office. The doors entered directly into the home w no means of prevention; locks were external to the...

Melanie S.

includes taxes & fees

3 Sept - 4 Sept

A two-story house with a front porch, a small garage, and a well-maintained garden with stepping stones and flowering plants.

18. “Brookshire Cottage” Acadia National Park “Pet Friendly” Mt Desert Island ME

Tremont

Krisa H.

includes taxes & fees

3 Sept - 4 Sept

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

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

southwest harbor

Michael Q.

includes taxes & fees

2 Sept - 3 Sept

A living room with a blue door, a fireplace, a sofa with cushions, a coffee table, and a television displaying a scenic view.

20. Quietside Quarterdeck: Dual King Wings, Bunk Room, Fire Patio & Pet-Friendly

Southwest Harbor

"PERFECTION, HIGHLY RECOMMEND!! This house was the absolute perfect spot for visiting Acadia and the Bar Harbor area! SW Harbor is quaint & quiet, with really great restaurants - all very walkable from the house. And then there's the house itself - from its own parking area to the homey beautifully curated decor to the functional separate wings of the house to the super fun finished basement lounge - and I could go on!!! On top of all that, the host's communication is clear, thorough, and rapid....

Rachel D.

includes taxes & fees

8 Sept - 9 Sept

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Top Winter Harbor Hotel Reviews

Comfort Inn Ellsworth - Bar Harbor

10/10 Excellent

"My stay was amazing. The room was very clean, and the staff was very nice."

Bar Harbor Manor

8/10 Good

"A good 10mins walk from the Harbor so not at all central. These are rooms in a converted building so rooms in odd places and no elevator. No pool/hottub. Breakfast and parking included. Continental Breakfast was good but no real dining facilities (just a few table and chairs) - so it was "grab and go" as opposed to sit down."

Find out more about Winter Harbor

Winter Harbor Holiday Homes information

Number of reviews	419
Accommodation	854 Holiday Homes
Lowest Price	£84
Highest Price	£999

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Harbor holiday homes

1. Water access house Acadia National Park Schoodic Point

2. House Acadia at Gallagher`s Travels

3. Tranquility by the Bay!

4. Sun Shed Farm Stay

5. Cozy Milbridge Country Home

6. The Colonels Suites

7. Wildwood Cottage at Gallagher`s Travels

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

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

10. Have an unforgettable getaway at a family sized beach house with private beach!

11. Booking now for summer & fall 2026-explore Acadia, Bar Harbor, Downeast Maine

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

13. Acadia Retreat- 3 bedroom, 2 bath on two private serene acres

14. Beautiful Bar Harbor House

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

16. Lumberjack Cottages

17. Beautiful Bar Harbor House

18. “Brookshire Cottage” Acadia National Park “Pet Friendly” Mt Desert Island ME

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

20. Quietside Quarterdeck: Dual King Wings, Bunk Room, Fire Patio & Pet-Friendly

Find holiday rentals that suit your style

Top Winter Harbor Hotel Reviews

Comfort Inn Ellsworth - Bar Harbor

The Pathmaker Hotel

Bar Harbor Manor

Main Street Motel

Wonder View Inn - Bar Harbor Collection

Acadia Gateway Motel

Terramor Outdoor Resort

Find out more about Winter Harbor

Winter Harbor Holiday Homes information

Explore a world of travel with Expedia