
Cottage vacation rentals in Islesboro
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Top-rated cottage rentals in Islesboro
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Popular amenities for Islesboro cottage rentals
Cottage rentals with a hot tub

Oceanfront Family Getaway - 8BR/6BA/5Acres
The most beautiful place, exceeding all expectations. The views are spectacular. We breathed in peace and tranquility. A fabulous place to celebrate my 80th birthday with the whole family -- 16 of us. Everyone was comfortable in the space. In addition to being the perfect host, Samantha provided surprise extras which was such fun! Just a few of the highlights: S'mores at the firepit, lobster dinners, seals, bald eagles and fireworks. She made our stay truly memorable. My family gives the place the highest recommendation.

Maine Cottage - HOT TUB, Dead End, 100+ft shore.
Spent quite a while here for work and saw winter turn to spring. What an amazing place to stay! Right on the water, great views, and it’s so peaceful. Thanks Craig for being so flexible! Everything was up to par and then some. I hope to come back in the summer sometime and enjoy it again!

Lakeview Cottage
Wonderful place right on the lake. Hugo was super responsive. We had a great time.

11 Cute 1Br Acadia Cottage Open Hearth Inn
We stayed here our last night while visiting Acadia. Super cute little cabin! We loved that they had a common space in the main house that was full of supplies and very welcoming. Would stay here again!

Canoe House Bungalow and Spa Retreat ,Searsport
The bungalow is cozy and comfortable. We throughly enjoyed the walk through the woods and sauna. Mayya goes above and beyond as a host! She is extremely kind and attentive. Highly recommend!

Lawn Cottage - Newly Renovated 2024
Adorable cottage, newly renovated. Perfect for two with an open space loft for one more. Kitchen is well stocked right down to the coffee. A good location if visiting Fort Knox, Mt. Barrie and not too far from Bar Harbor if that is on your list. Great stay, highly recommend. Beautiful view and private.

Nashport on the Penobscot
great stay for a relaxing weekend trip. perfect house for chilling but still drivable to Acadia. well stocked on the essentials, linens, and stunning views! host very responsive as well.

Megunticook Retreat
We’ve stayed in a lot of Airbnbs across the country and I’m not exaggerating when I say that Lydia’s place was one of the cleanest and most well-maintained homes that we’ve been in. The property and scenery are breathtaking. The numbers of birds and chipmunks that entertained us while we sat on the back deck was surprising. We ate all of our meals with the exception of lunches at the cabin and had everything we needed to prep and cook our food. This trip was all about relaxing and Lydia’s home was everything we needed.
Pet-friendly cottage rentals

Up Back Cottage
Eric is a super friendly host and he knows the local recommendations. His cabin is easy to check-in, clean and very peaceful. One sidenote is this listing doesn't provide wifi, making it ideal for people looking for an unplugged getaway. We truly enjoyed our time on the beautiful Maine coast!

Chic Farmhouse Cottage, WiFi, Private Beach, A/C
Absolutely loved our stay here! If you're someone who enjoys being close to nature and traveling with your dog, this place is perfect. The surroundings are peaceful and green. Fabiola was super friendly and made everything easy from check-in to check-out. The house rules were clear and straightforward, which made the whole experience stress-free. We felt really welcomed and comfortable the entire time. All in all, a great stay—we’d definitely come back!

Cozy, tranquil forest retreat, 10 min. to coast
(Written by Keith’s wife 🤣) : I am going to miss the conversation with Linsay! There became a point where I almost felt lost if I didn’t talk to her at least once a day! Lol 😂 We were supposed to return on 3/9, and Linsay had blocked time off for us, but plans changed and she was SO understanding!! Love her to pieces! ❤️ We will DEFINITELY be coming back just to visit - in warmer weather of course! Maine can keep their winters! 😂

Our charming,oceanfront, Bradford point cottage
Jeff’s place stood out as a beautiful relaxing and peaceful location. The cottage was exactly what was advertised. Everything we needed was available to us. Felt like our cottage in NY. Thoroughly enjoyed it. Would love to return. Response was great.

Hermit Thrush House
The Hermit Thrush House is cozy, charming, and quiet. I slept better than I have in a long time! Everything we needed was there. My mom and I visit MidCoast Maine every fall, and this was our first stay at the Hermit Thrush House. We picked a great place close to all the towns we love to visit. Very nice!

Waterscape Cottage - private waterfront
We loved staying at Ann's place! It was exactly what we wanted, close to town and to lots of activities but also felt remote and in a really gorgeous location. Great, rustic spot.

Cozy cottage close to Acadia National Park!
Such an absolutely magical place to stay! My pup and I stayed for a month while I worked and played. Gorgeous views of the Beech Hill Pond and close enough to various towns for hiking, sightseeing and enjoying local food. Spent time on Deer Isle, MDI at Bar Harbour & Acadia, and even made the trek to Lubec. if you want to experience a wee bit of winter and early spring, mid to late March into April was the perfect time. We had a few inches of snow fall within the first few days of the trip. Don't hesitate to book this cottage!

Katy's Seaside Cottage
Super comfortable. Good kitchen for cooking, nice outdoor area. Good recycling and composting, super nice neighbors. Felt right at home.
Private cottage rentals

Sunny 2 Bedroom cottage - Walk to the beach!
Megan’s Lincolnville house was peaceful and cozy, just right for a friends weekend getaway. Would have loved to stay for a week or more. Nice to stay there before the busyness of the season. We easily went between Belfast, Camden and the charming Rockport. Don’t miss Mt Battie and all the waterfront areas. You can see the water across the street and the green expanse behind the house. We liked seeing the old house next door being restored .

Stylish ocean-view home on Acadia's Schoodic Loop
The location is amazing — just down the road from Acadia, on the Schoodic Peninsula, which in my opinion is even more pristine and beautiful than the main part of the park. The cabin itself is incredible — warm, spotless, charming, and very well-stocked. Beautiful views of the water, super relaxing vibes. I especially loved the sunroom and the deck — perfect for unwinding! The host was super friendly, helpful, and incredibly responsive — made everything so easy and welcoming. We hope to be back soon!

Cozy Cottage on u pick blueberry farm.
I had to stay a extra night because of work. The host had the place cleaned and ready before returning to the house which was really nice. it a cool house with great property to walk.

Nestled between Rockland and Camden,
Our stay at Linda’s was perfect. The setting was quiet, secluded, peaceful and relaxing. Easy access to Camden, Rockport and Rockland—the perfect location. Very clean with many amenities. Linda met us on arrival and showed us around. She had fresh fruit and muffins for us and gave good restaurant and activity recommendations. She was friendly, helpful, and attentive to our needs. She is a super host and a super lady! We highly recommend her and will stay with her again on our next visit to Camden!

Andaru
Great location with beautiful views. Quiet quaint neighborhood. Cool house, remodeled well.

Cozy waterfront home on Merrymeeting Bay.
Loved our time here! It’s about a 40 minute drive from Portland and then 5-10 from Brunswick. The neighborhood is quiet and perfect, exactly what we needed to relax! We loved coming back from Portland and grabbing dinner and gelato in Brunswick, such a nice way to unwind from a long day. Highly recommend and would love to stay here again :)

Oak Grove Cottage at Sennebec Pond
I have zero complaints about Gordon's home. Everything was accurately described and the property was beautiful! it is right on the pond and the pictures do it justice. Yes, it's a little small and gets cold in the winter but it's worth it if you want to stay somewhere pretty without breaking the bank. Also, he has 3 heaters. We didn't leave them on because we were gone a lot of the time but it probably would have stayed warm if we did. This is really a great property for a couple! Highly recommended.

Short walking distance to the Town of Stonington
Words cannot express how much my husband and I enjoyed Chelsea's cottage. It was everything and more in what we were hoping for. Chelsea and her husband went out of their way to help provide us with a truly authentic experience as we wrapped up our 2 week road trip through Maine. We highly recommend without hesitation the area, the cottage and gracious hospitality we received.
Quick stats about cottage rentals in Islesboro
Total rentals
30 properties
Nightly prices starting at
G$16,786 GYD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Acadia National Park
- Pemaquid Beach
- Samoset Resort
- Pemaquid Point Lighthouse
- Northeast Harbour Golf Club
- Coastal Maine Botanical Gardens
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Spragues Beach
- Pinnacle Park
- Eaton Mountain Ski Resort
- Sand Beach
- Kebo Valley Golf Club
- Pebbly Beach
- Rockland Breakwater Light
- Narrow Place Beach
- Bear Island Beach
- Three Island Beach
- Pebble Beach
- Indian Camp Beach
- Lighthouse Beach
- Hero Beach
- Farnsworth Art Museum
- The Camden Snow Bowl