A calm lake with a dock, boats, and a forested shoreline.

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Islesboro vacation homes

1. Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (4 reviews)
"The home is clean and very well stocked with anything you might need. Ty reached out to me to make sure everything was good and offered to bring anything I might need while staying there. Property is very well kept. I love the neighbors too. Bed was comfortable. We will be back next year."
United States
Sheila D.
The price is ￥30,704
￥53,236 total
includes taxes & fees
Sep 1 - Sep 2
Romantic Coastal Escape near Harbor
A covered patio with a round table and chairs, a sign reading "Life's at ease with an ocean breeze," and a view of a lake and houses in the distance.

2. Privately owned water view cottage with fabulous views of Penobscot Bay!

Privately owned water view cottage with fabulous views of Penobscot Bay!
Belfast
10.0 out of 10, Exceptional, (75 reviews)
"Lovely stay. "
United States
Anne O.
Privately owned water view cottage with fabulous views of Penobscot Bay!
A wooden dock leading to a beach with a picnic table and chairs, surrounded by greenery.

3. Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (25 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is ￥40,409
￥84,103 total
includes taxes & fees
Sep 16 - Sep 17
Waterfront Getaway Near Acadia w/ Spectacular View
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

4. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (31 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is ￥17,194
￥26,030 total
includes taxes & fees
Sep 15 - Sep 16
Simplicity-Just what you need! STR24-20
A large, light-colored house with a garage, surrounded by lush greenery and a lake.

5. Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!

Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
Penobscot
Magical Home & Setting on Reversing Falls. Kayaks, Recreation, Beauty & FUN!
A covered porch with a grill, a potted plant, and a small table.

6. Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
10.0 out of 10, Exceptional, (15 reviews)
"This is a great place, nice and quiet, very clean and cozy. Loved it here!!"
United States
Lorna W.
The price is ￥51,704
￥94,160 total
includes taxes & fees
Aug 30 - Aug 31
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
A modern kitchen with a central island, white cabinetry, and a stainless steel range hood.

7. Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (26 reviews)
"Everything was great but at this price the expectation is better and clearer coffee pot and softer toilet tissue. Three large king beds were excellent, better than expected. Bath towels also were excellent size and quality. We knew and we're able to manage with only one and half bath but if you have more people staying at the property, then only one shower may delay in every body getting ready."
United States
Anil
The price is ￥36,540
￥90,117 total
includes taxes & fees
Aug 30 - Aug 31
Tides' Reach - Private Waterfront King Beds
A wooden deck with Adirondack chairs and a grill.

8. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
8.8 out of 10, Excellent, (10 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
The price is ￥23,068
￥43,699 total
includes taxes & fees
Sep 1 - Sep 2
Bright 2-Bedroom Apartment Near Downtown Thomaston
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

9. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful house with a beautiful location!"
United States
Angel H.
The price is ￥35,329
￥82,041 total
includes taxes & fees
Aug 31 - Sep 1
Harbor/🦞 Pound Access & Views from Large Deck
A two-story house with a dark exterior, a balcony, and a well-maintained garden with rocks and plants.

10. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (70 reviews)
"Perfect home away from home. Very well stocked kitchen, the beds were very comfy and everything was just overall cozy. Such a serene location. We will definitely stay again next time we come to visit our grandkids. "
United States
Tina B.
The price is ￥28,636
￥90,172 total
includes taxes & fees
Aug 30 - Aug 31
Oceanview Bungalow Style Home in Owls Head
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

11. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (51 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is ￥24,676
￥49,629 total
includes taxes & fees
Sep 22 - Sep 23
2 Bedroom Close to Town Home
A wooden cabin-style kitchen with a central dining table, wooden cabinets, and a hanging light fixture.

12. Relaxing Two Bedroom Cabin - 10 minutes to Camden!

Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
8.0 out of 10, Very Good, (5 reviews)
"We booked this place for Memorial Weekend, and drove into Camden to explore the town. Host was so friendly and responsive, the cabin was so clean and quaint/cute, loved the location that we go that cabin feel but could drive a short distance to get into town/harbor, and overall had a great time! "
United States
Kimberly
The price is ￥51,704
￥94,160 total
includes taxes & fees
Aug 30 - Aug 31
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

13. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (38 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is ￥27,204
￥52,716 total
includes taxes & fees
Sep 15 - Sep 16
Peaceful, Centrally Located Home with Seasonal River Views
A room with a large window offering a view of a snowy landscape and a body of water.

14. Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (97 reviews)
"Great location close to town"
United States
Rich W.
The price is ￥39,773
￥71,445 total
includes taxes & fees
Sep 7 - Sep 8
Comfortable, Close to Town Home, with Oceanview.
A waterfront marina with boats docked, a large tree in the foreground, and a building with a gabled roof.

15. Maine Coast Mountain Retreat

Maine Coast Mountain Retreat
Camden
10.0 out of 10, Exceptional, (11 reviews)
"The house is beautiful, with tons of wonderful decorations. The owners are very welcoming and great to deal with. The house is located very close to downtown Camden, so we got to take a relaxing walk every day to see the sights. We had a great stay and hope to visit again. "
United States
Danielle W.
The price is ￥87,500
￥116,011 total
includes taxes & fees
Sep 2 - Sep 3
Maine Coast Mountain Retreat

16. Historic Captain's House on shore of Penobscot Bay

Historic Captain's House on shore of Penobscot Bay
Searsport
The price is ￥85,909
￥106,993 total
includes taxes & fees
Aug 31 - Sep 1
Historic Captain's House on shore of Penobscot Bay
A cozy room with a large arched window, a potted plant on a wooden side table, and two white armchairs.

17. Inkwell Suite at Spofford Lodge

Inkwell Suite at Spofford Lodge
Bucksport
10.0 out of 10, Exceptional, (18 reviews)
"Property was very nice, clean and Lisa our host was very nice and helpful. Great place, highly recommend!"
United States
brian g.
The price is ￥30,275
￥47,024 total
includes taxes & fees
Sep 14 - Sep 15
Inkwell Suite at Spofford Lodge
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

18. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (39 reviews)
"Great place at a great price! I look forward to staying there again. "
United States
Stephen H.
The price is ￥34,363
￥72,484 total
includes taxes & fees
Aug 31 - Sep 1
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A wooden deck with a grill, chairs, and a table, overlooking a forested area.

19. Waterfront Deer Isle Retreat w/ Fire Pit!

Waterfront Deer Isle Retreat w/ Fire Pit!
Deer Isle
10.0 out of 10, Exceptional, (6 reviews)
"Excellent accommodations with lovely natural surroundings."
United States
Sara
The price is ￥47,919
￥119,040 total
includes taxes & fees
Sep 20 - Sep 21
Waterfront Deer Isle Retreat w/ Fire Pit!
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

20. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.6 out of 10, Excellent, (14 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is ￥28,318
￥40,842 total
includes taxes & fees
Aug 30 - Aug 31
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Islesboro Hotel Reviews

Cedar Crest Inn

Cedar Crest Inn

10/10 Excellent
"The room was clean, the staff was great. Good location and easy parking."
Denise 1-night trip
Posted 2 hours ago
Cedar Crest Inn

Find out more about Islesboro

Islesboro Vacation Homes information

Number of reviews
610
Accommodation
560 Vacation Homes
Lowest Price
￥26,030
Highest Price
￥119,040