Cottage vacation rentals in Islesboro

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Popular amenities for Islesboro cottage rentals

Cottage rentals with a hot tub

Superhost
A bright living area features large windows offering views of the water and trees. A comfortable blue sofa is positioned near a wooden coffee table, while a small TV sits on a stand. Skylights provide natural light, enhancing the inviting and spacious feel.
Cottage in Cushing
4.82 out of 5 average rating, 22 reviews

Oceanfront Family Getaway - 8BR/6BA/5Acres

BarbieRating, 5 stars10 months ago
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.
Guest favorite
A serene view of a lake is captured at sunset, with vibrant shades of purple and pink reflecting off the water's surface. The shoreline is lined with trees, creating a peaceful atmosphere in this natural setting.
Cottage in Madison
4.83 out of 5 average rating, 40 reviews

Maine Cottage - HOT TUB, Dead End, 100+ft shore.

KyleighRating, 5 stars1 month ago
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!
Superhost
A wooden dock extends over calm waters, accompanied by two Adirondack chairs positioned to enjoy the view. Lush green trees frame the scene, while distant hills are visible in the background, creating a serene lakeside atmosphere.
Cottage in Ellsworth
4.94 out of 5 average rating, 49 reviews

Lakeview Cottage

NathanRating, 5 stars3 weeks ago
Wonderful place right on the lake. Hugo was super responsive. We had a great time.
Guest favorite
A row of rustic cottages is set against a backdrop of lush greenery and tall trees. Each cottage features a red door with window shutters and picnic tables positioned on a gravel path, inviting guests to enjoy the outdoors.
Cottage in Trenton
4.93 out of 5 average rating, 96 reviews

11 Cute 1Br Acadia Cottage Open Hearth Inn

BethRating, 5 stars2 weeks ago
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!
Guest favorite
A serene outdoor space features a cozy fire pit surrounded by log seating, amid a lush green forest. The rustic bungalow, with its wooden siding and large windows, sits adjacent to a wooden sauna. A patio umbrella provides shade over the entrance.
Cottage in Searsport
4.93 out of 5 average rating, 102 reviews

Canoe House Bungalow and Spa Retreat ,Searsport

MamieRating, 5 stars7 months ago
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!
Guest favorite
A vast expanse of greenery is visible beyond the wooden railing, framed by a clear blue sky. The horizon reveals a calm body of water, creating a serene backdrop against lush trees and shrubs that define the landscape.
Cottage in Belfast
4.88 out of 5 average rating, 24 reviews

Lawn Cottage - Newly Renovated 2024

CarolineRating, 5 stars1 week ago
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.
Guest favorite
The exterior of a two-story house is surrounded by a green lawn and neatly trimmed bushes. The home features multiple windows and a balcony. A flag is displayed on a pole, while trees and landscaping create a natural backdrop.
Cottage in Verona Island
4.89 out of 5 average rating, 171 reviews

Nashport on the Penobscot

DeanRating, 5 starstoday
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.
Top guest favorite
A charming cottage is nestled among vibrant autumn foliage. The exterior features a covered porch with two red chairs, a picnic table on a grassy lawn, and a nearby outdoor grill. Large windows accentuate the welcoming facade of the home.
Cottage in Camden
5 out of 5 average rating, 37 reviews

Megunticook Retreat

DebraRating, 5 stars1 week ago
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

Superhost
The cottage displays a natural wood exterior, framed by vibrant green foliage. A large screened-in porch offers access to the surroundings. A picnic table sits nearby, inviting outdoor meals. Pink rhododendron flowers add a pop of color, enhancing the serene woodland setting.
Cottage in Lamoine
4.96 out of 5 average rating, 113 reviews

Up Back Cottage

SophieRating, 5 stars1 week ago
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!
Top guest favorite
The well-maintained garden features lush greenery and a manicured lawn, with Adirondack chairs positioned for relaxation. A white picket fence encloses the space, separating a dog-friendly area. The surrounding trees add privacy and a natural backdrop to the outdoor setting.
Cottage in Blue Hill
4.97 out of 5 average rating, 116 reviews

Chic Farmhouse Cottage, WiFi, Private Beach, A/C

BálintRating, 5 stars1 week ago
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!
Guest favorite
The exterior of a charming cottage is shown, featuring a wooden facade with green accents. Flower boxes and potted plants adorn the front, adding color and life. The door is painted bright yellow, framed by two windows adorned with flowers, and a grassy area enhances the serene setting.
Cottage in Swanville
4.95 out of 5 average rating, 43 reviews

Cozy, tranquil forest retreat, 10 min. to coast

KeithRating, 5 stars3 months ago
(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! 😂
Guest favorite
A circular tree swing hangs from a sturdy branch, overlooking a spacious green yard. The view includes a serene body of water with a dock and distant islands framed by trees under a clear blue sky.
Cottage in Friendship
4.91 out of 5 average rating, 263 reviews

Our charming,oceanfront, Bradford point cottage

DeniseRating, 5 stars3 days ago
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.
Top guest favorite
The exterior of the guest house is shown, featuring a light-colored facade with large front windows. A wooden deck is accessible via steps on one side, while two garage doors are visible at the ground level. Surrounding greenery and a well-maintained lawn contribute to the inviting environment.
Cottage in South Bristol
4.97 out of 5 average rating, 103 reviews

Hermit Thrush House

KathiRating, 5 stars7 months ago
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!
Guest favorite
A charming cottage is nestled among tall trees, featuring a welcoming entrance with wooden doors. A small porch is adorned with a chair, providing a peaceful spot to enjoy the surrounding woodland. Multiple windows enhance the cabin's light-filled exterior.
Cottage in Wiscasset
4.88 out of 5 average rating, 273 reviews

Waterscape Cottage - private waterfront

SophieRating, 5 stars2 days ago
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.
Guest favorite
Cottage in Otis
4.96 out of 5 average rating, 100 reviews

Cozy cottage close to Acadia National Park!

MelissaRating, 5 stars1 month ago
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!
Guest favorite
A spacious deck features wooden chairs and a blue-striped lounge chair, providing a comfortable outdoor seating area. Light casts shadows along the gray wooden floor, with a view of the green lawn and surrounding trees in the background.
Cottage in Deer Isle
4.89 out of 5 average rating, 136 reviews

Katy's Seaside Cottage

MargaretRating, 5 stars2 weeks ago
Super comfortable. Good kitchen for cooking, nice outdoor area. Good recycling and composting, super nice neighbors. Felt right at home.

Private cottage rentals

Top guest favorite
A charming single-story cottage is surrounded by a lush green lawn. Large windows allow for ample natural light, and flower beds with colorful blooms adorn the entrance. A serene landscape with distant hills completes the tranquil scene under a partly cloudy sky.
Cottage in Lincolnville
5 out of 5 average rating, 75 reviews

Sunny 2 Bedroom cottage - Walk to the beach!

MarkRating, 5 stars4 weeks ago
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 .
Top guest favorite
Cottage in Gouldsboro
4.97 out of 5 average rating, 78 reviews

Stylish ocean-view home on Acadia's Schoodic Loop

JerryRating, 5 stars2 weeks ago
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!
Guest favorite
Cottage in Washington
4.9 out of 5 average rating, 358 reviews

Cozy Cottage on u pick blueberry farm.

RobertRating, 5 stars1 week ago
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.
Top guest favorite
The exterior of the cottage is presented, featuring a white front door framed by two charming wall lights. Vibrant potted flowers are positioned beside the entrance, while lush greenery surrounds the area, complementing the soft green siding of the house.
Cottage in Rockport
4.96 out of 5 average rating, 99 reviews

Nestled between Rockland and Camden,

MargaretRating, 5 stars9 months ago
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!
Guest favorite
Cottage in Northport
4.9 out of 5 average rating, 20 reviews

Andaru

WilliamRating, 5 stars3 weeks ago
Great location with beautiful views. Quiet quaint neighborhood. Cool house, remodeled well.
Guest favorite
A vibrant cluster of pink flowers is set against a backdrop of green trees and a scenic waterfront view. The water is visible through the foliage, with sandy beach areas outlined in the distance. Sunlight illuminates the landscape, enhancing the natural beauty.
Cottage in Topsham
4.93 out of 5 average rating, 253 reviews

Cozy waterfront home on Merrymeeting Bay.

EmilyRating, 5 stars5 days ago
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 :)
Top guest favorite
Cottage in Appleton
5 out of 5 average rating, 21 reviews

Oak Grove Cottage at Sennebec Pond

RyanRating, 5 stars8 months ago
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.
Top guest favorite
A stainless steel pot filled with freshly cooked crab claws rests on a black table. The partially visible harbor offers a view of boats and a shoreline in the background, framed by a white railing. Natural light enhances the colors of the crab and the setting.
Cottage in Stonington
5 out of 5 average rating, 19 reviews

Short walking distance to the Town of Stonington

AmyRating, 5 stars1 week ago
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

Destinations to explore

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  2. United States
  3. Maine
  4. Waldo County
  5. Islesboro
  6. Cottage rentals