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Winter Harbor Vacation Rentals & Cabin Rentals - 38 Rentals Available

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38 Vacation rentals

(5)

1 / 21

Winter Harbor House

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Private garden

Responds fast! Avg. 17 minutes

$254.00

Excellent (5 reviews)

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from $254.00 / night

(4)

1 / 25

Winter Harbor House

  • 3
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 17 minutes

$221.00

Excellent (4 reviews)

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from $221.00 / night

1 / 13

Winter Harbor Cottage

  • 1
  • 2
  • 7 nights min
  • Private garden

Responds fast! Avg. 17 minutes

$221.00

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from $221.00 / night

Your search has been expanded 17.7 miles to include more rentals

(6)

1 / 8

Southwest Harbor Log cabin - 16.5 miles away

  • 2
  • 6
  • 7 nights min
  • Child friendly

Responds fast! Avg. 1 hour 17 minutes

“Great cottage to serve as a headquarters to a Mount Desert Island vacation. Kept real clean. Nice balcony for BBQ and cozy coffee in the morning. Two minutes to Pretty Marsh (Acadia National Park), a great place to view the sunset. I would give...”
- Review left on 07/25/2016

$197.00

Very Good (6 reviews)

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from $197.00 / night

1 / 8

Southwest Harbor Cottage - 14.2 miles away

  • 1
  • 2
  • 7 nights min
  • Private garden

$167.00

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from $167.00 / night

(12)

1 / 17

Mount Desert Log cabin - 14.2 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
“This is our second time at the cabin. It?s absolutely fabulous. It?s a great place to spend long mornings taking your time and watching the loons...”
- Review left on 08/18/2019

$189.00

Excellent (12 reviews)

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from $189.00 / night

(4)

1 / 11

Milbridge Cottage - 13.5 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Child friendly
  • Pet friendly
“The ocean is feet from the deck at high tide. Wonderful. Comfortable living. Bathrooms and kitchen are small and by no means fancy but well-equipped. The "master" bedroom has two twin beds, and there are two small rooms each with two bunk beds, and...”
- Review left on 09/23/2014

$195.00

Excellent (4 reviews)

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from $195.00 / night

1 / 5

Seal Cove Cottage - 16.5 miles away

  • 2
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 1 hour 45 minutes

$164.00

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from $164.00 / night

(3)

1 / 12

Southwest Harbor Apartment - 14.6 miles away

  • 1
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly

Responds fast! Avg. 1 hour 45 minutes

$224.00

Excellent (3 reviews)

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from $224.00 / night

1 / 7

Seal Cove Cottage - 16.4 miles away

  • 2
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 45 minutes

$164.00

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from $164.00 / night

(1)

1 / 6

Seal Cove Cottage - 16.4 miles away

  • 2
  • 7
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 1 hour 45 minutes

$197.00

Excellent (1 reviews)

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from $197.00 / night

(5)

1 / 28

Bar Harbor House - 6.3 miles away

  • 3
  • 7
  • min stay varies
  • Child friendly
  • Air conditioning
“This place was absolutely wonderful. The house was everything we hoped for and more. It was immaculate when we arrived. The home is new and decorated beautifully. A lot of effort was put into making this home away from home. We loved the location...”
- Review left on 10/18/2016

$298.00

Excellent (5 reviews)

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from $298.00 / night

1 / 24

Bar Harbor House - 6.3 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

$230.00

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from $230.00 / night

(2)

1 / 34

Bar Harbor House - 6.3 miles away

  • 4
  • 6
  • min stay varies
  • Child friendly
  • Pet friendly

$230.00

Excellent (2 reviews)

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from $230.00 / night

1 / 16

Southwest Harbor House - 17.7 miles away

  • 3
  • 7
  • 7 nights min
  • Child friendly
  • Private garden

Responds fast! Avg. 1 hour 56 minutes

$625.00

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from $625.00 / night

(16)

1 / 29

Southwest Harbor Cottage - 17.5 miles away

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

Responds fast! Avg. 1 hour 56 minutes

$459.00

Excellent (16 reviews)

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from $459.00 / night

(33)

1 / 31

Southwest Harbor House - 17.5 miles away

  • 4
  • 9
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

Responds fast! Avg. 1 hour 56 minutes

$516.00

Excellent (33 reviews)

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from $516.00 / night

(2)

1 / 28

Bar Harbor Cottage - 9.9 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly

$210.00

Very Good (2 reviews)

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from $210.00 / night

(6)

1 / 24

Trenton Cottage - 15.1 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Pet friendly

$240.00

Excellent (6 reviews)

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from $240.00 / night

(2)

1 / 22

Mount Desert Cottage - 14.3 miles away

  • 2
  • 8
  • 7 nights min
  • Child friendly
  • Pet friendly

$450.00

Excellent (2 reviews)

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from $450.00 / night

(12)

1 / 15

Bar Harbor Apartment - 11.9 miles away

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Pet friendly

$98.00

Excellent (12 reviews)

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from $98.00 / night

(5)

1 / 32

Bar Harbor House - 5.8 miles away

  • 6
  • 15
  • min stay varies
  • Child friendly

$375.00

Excellent (5 reviews)

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from $375.00 / night

(1)

1 / 22

Mount Desert Log cabin - 15.3 miles away

  • 2
  • 4
  • 7 nights min
  • Child friendly

$165.00

Excellent (1 reviews)

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from $165.00 / night

(13)

1 / 31

Mount Desert Cottage - 12.8 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly

$210.00

Excellent (13 reviews)

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from $210.00 / night

(4)

1 / 15

Bar Harbor House - 6.1 miles away

  • 1
  • 4
  • 7 nights min
  • Child friendly

$117.00

Very Good (4 reviews)

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from $117.00 / night

(10)

1 / 24

Bar Harbor House - 6.1 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly

$210.00

Very Good (10 reviews)

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from $210.00 / night

1 / 31

Bar Harbor Apartment - 8.2 miles away

  • 1
  • 3
  • 7 nights min
  • Child friendly

$135.00

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from $135.00 / night

(10)

1 / 21

Bar Harbor House - 13.3 miles away

  • 4
  • 6
  • 7 nights min
  • Child friendly

$256.00

Very Good (10 reviews)

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from $256.00 / night

(6)

1 / 11

Bar Harbor Apartment - 6.1 miles away

  • 2
  • 4
  • min stay varies
  • Child friendly

$165.00

Excellent (6 reviews)

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from $165.00 / night

(15)

1 / 20

Bar Harbor House - 6 miles away

  • 4
  • 10
  • 7 nights min
  • Child friendly

$225.00

Excellent (15 reviews)

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from $225.00 / night

(4)

1 / 9

Bar Harbor Apartment - 6.1 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly

$165.00

Very Good (4 reviews)

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from $165.00 / night

(2)

1 / 27

Bar Harbor House - 11.7 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

$225.00

Excellent (2 reviews)

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from $225.00 / night

(5)

1 / 17

Bar Harbor House - 6.1 miles away

  • 2
  • 5
  • 7 nights min
  • Child friendly

$165.00

Excellent (5 reviews)

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from $165.00 / night

1 / 19

Bar Harbor Apartment - 6.3 miles away

  • 1
  • 2
  • min stay varies
  • Child friendly

$132.00

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from $132.00 / night

(6)

1 / 27

Bar Harbor House - 6 miles away

  • 3
  • 8
  • 7 nights min
  • Child friendly

$233.00

Excellent (6 reviews)

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from $233.00 / night

(6)

1 / 32

Bar Harbor House - 11.3 miles away

  • 7
  • 12
  • 7 nights min
  • Child friendly

$525.00

Very Good (6 reviews)

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from $525.00 / night

(28)

1 / 24

Gouldsboro Log cabin - 5 miles away

  • 2
  • 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly

Responds fast! Avg. 1 hour 20 minutes

“We loved our stay at Tugwassa Cottage. Anne was a most friendly and accommodating host. The cottage was clean, with a distinct personality that was so comfortable and unique. The location was perfect, the views spectacular, and within easy...”
- Review left on 10/13/2015

$167.00

Excellent (28 reviews)

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from $167.00 / night

(7)

1 / 13

Hancock Cottage - 8.5 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 2 hours 44 minutes

“The cabin was a delight and we didn't want to leave. Comfortable, cozy, surprisingly roomy. In rain and shine this was a beautiful spot to spend time on the coast of Maine. Well equipped kitchen, inviting spaces, and an unsurpassed view of Mt....”
- Review left on 08/15/2016

$197.00

Excellent (7 reviews)

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from $197.00 / night