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Compare 148 Cottages in Islesboro with updated reviews, rates, and availability.

Waterfront cottage with deep water dock, ocean front.
Exterior

Waterfront cottage with deep water dock, ocean front.

10.0 out of 10, Exceptional, (88)
"We thoroughly enjoyed our stay at the cabin. It had all we needed and the radiant heat in the floor was a plus! We enjoyed the town and plan to return in the future ! Thanks Jon !"
Waterfront cottage with deep water dock, ocean front.
Pine Grove Cottages
Property grounds

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (86)
"It was a wonderful and relaxing time! Great communication between staff. "
Pine Grove Cottages
2 bedroom cottage house at Pond Hill Farms
Miscellaneous

2 bedroom cottage house at Pond Hill Farms

10.0 out of 10, Exceptional, (5)
"We love to support small farms when we travel and this was a convenient location in between our plans in Portland and Acadia. The cottage is at the top of the hill with panoramic views. We woke up to thick fog which blanketed the scenery in clouds and made for scenery which we don't often get to see. The cottage is brand new and very clean and comfortable. We were sad we only stayed one night. The driveway is a bit steep and not paved. Our SUV handled it fine but a smaller car may have a bit of...
2 bedroom cottage house at Pond Hill Farms
Oceanfront and Pet Friendly Cottage

Oceanfront and Pet Friendly Cottage

9.6 out of 10, Exceptional, (7)
"The quiet relaxing cottage and area was what I need to escape the AZ heat for a week! Enjoyed taking my dog for walks on the beach and everyone was very friendly. The cottage was very clean and once I was able to get the WiFi connected it was a great place to get some work done while having the ocean view. Would have stayed longer if there was an option to do laundry as other Vrbo’s in the area have."
Oceanfront and Pet Friendly Cottage
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range

9.0 out of 10, Wonderful, (17)
"For a small cottage it was spacious, had modern amenities. The listing says harbor view but you have to look thru power lines, power poles and a lobster processing plant. The side stone steps are overgrown with vegetation making it hard to maneuver. All in all a good experience."
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Cozy Cottage on Blue Hill Farm
King in loft

Cozy Cottage on Blue Hill Farm

9.6 out of 10, Exceptional, (73)
"Amazing cottage with all the amenities! It was our first visit to Blue Hills and it was so Much fun! I would highly recommend this lovely cottage on the farm!!!"
Cozy Cottage on Blue Hill Farm
Breathtaking Oceanfront Private Cottage
Beach

Breathtaking Oceanfront Private Cottage

10.0 out of 10, Exceptional, (60)
"Stayed for a longweekend in November. The cottage by the sea is literally right on the sea, the views are breathtaking, the sunrise gorgeous and we were lucky to have beautiful weather. The host thought of everything, the cottage has everything you need to make a wonderful stay. Would definitely return. Rockland is about a 15 min drive and a great place to visit."
Breathtaking Oceanfront Private Cottage
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
Interior

~ Peaceful And Quaint Family Cottage On An Island In Maine ~

9.8 out of 10, Exceptional, (44)
"We just finished a five-night stay at this property. Rustic is the perfect way to describe it along with offering modern amenities like 1 and 1/2 baths, a complete kitchen, washer dryer and great internet. It's a great secluded location with the General Store just a five minute drive away."
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
Quiet & Lovely Lakefront Cottage for Families!
Union Vacation Rental | 3BR | 1BA | 1-Story Cottage | Stairs Required for Access

Quiet & Lovely Lakefront Cottage for Families!

9.6 out of 10, Exceptional, (13)
"Loved this spot. The lake was beautiful. We had a wonderful time even though the weather was bad a few days. The cabin was so cute and decorated very nice. The kitchen was stocked well. We had everything we needed. Loved hearing the loons at night. It wasn't too far from Camden that we visited frequently. I hope to come back there some day."
Quiet & Lovely Lakefront Cottage for Families!
A Cozy Nautical Nest on Lincolnville Beach
Pick up your favorite wine at Cellardoor Winery just 7 minutes from the Nest!

A Cozy Nautical Nest on Lincolnville Beach

9.6 out of 10, Exceptional, (4)
"We loved the location. Close to great hiking, restaurants and sites. "
A Cozy Nautical Nest on Lincolnville Beach
Cozy cottage-Winter Special. Book 3 nights in Dec-Feb and receive 150 cash back.
Terrace/patio

Cozy cottage-Winter Special. Book 3 nights in Dec-Feb and receive 150 cash back.

10.0 out of 10, Exceptional, (12)
"A beautifully built and decorated cottage in an awesome setting. Pictures don’t do it justice. All of the amenities and then some were provided. Lindsey and Michael made sure we had complete details on how to reach the cottage and checked in regularly to be sure we had no questions or concerns. Then there were the amazing treats and special Maine treat they also left for us. If there was a 10 star rating we would have given that. Lindsey and Michael should be considered superhosts. ...
Cozy cottage-Winter Special. Book 3 nights in Dec-Feb and receive 150 cash back.
Oak Point Cottage - Waterfront with a great beach
Exterior

Oak Point Cottage - Waterfront with a great beach

9.8 out of 10, Exceptional, (9)
"Loved the house and the location,but the house was not cleaned from the previous guests..fortunately the folks who rented before us weren't messy..i had to put my girlfriend to work cleaning toilets,making beds and doing the last guests laundry, but other than that house and property were awesomr"
Oak Point Cottage - Waterfront with a great beach
Back to basics small simple cottage just a two minute drive to the beach.
Room

Back to basics small simple cottage just a two minute drive to the beach.

Back to basics small simple cottage just a two minute drive to the beach.
Secluded Orland Cottage w/ Grill, Near State Parks
Living area

Secluded Orland Cottage w/ Grill, Near State Parks

3.0 star property
Secluded Orland Cottage w/ Grill, Near State Parks
Cozy Cottage on Cat Cove w/ Wraparound Deck!
Stonington Vacation Rental | 3BR | 1BA | Step-Free Access | Steep Hill to Water

Cozy Cottage on Cat Cove w/ Wraparound Deck!

7.6 out of 10, Good, (10)
"Grill did not work. "
Cozy Cottage on Cat Cove w/ Wraparound Deck!
Overlook Cottage, Toddy Pond!
Beach

Overlook Cottage, Toddy Pond!

8.8 out of 10, Excellent, (44)
"We had a wonderful stay at the Overlook. The view was fantastic, use of kayaks & fire pit was great & we totally relaxed with our pup. The only thing we could have used was info on where the transfer station was, how to get the bedroom TV to work (we figured it out, though) & a starter roll of paper towels. Aside from these minute issues, this is a wonderful cabin to escape to! I’d definitely stay here again! "
Overlook Cottage, Toddy Pond!
Winter Rate: 1k month Nov -Mid May. Convo for details!
You've Arrived! Street view of Crabapple Cottage

Winter Rate: 1k month Nov -Mid May. Convo for details!

9.8 out of 10, Exceptional, (22)
"Great place. Everything's just as described. "
Winter Rate: 1k month Nov -Mid May. Convo for details!
Quaint Cottage on Swan Lake
Property grounds

Quaint Cottage on Swan Lake

9.8 out of 10, Exceptional, (6)
"We were here for a week and had a great time! The house is quite small but well equipped for a short stay. The lake is beautiful and we had fun swimming as well as putting the kayaks to use. Pretty close to a local grocery and about 20 minutes to Belfast."
Quaint Cottage on Swan Lake
House At The Point - Rustic Cottage on Ocean's Edge
Terrace/patio

House At The Point - Rustic Cottage on Ocean's Edge

9.8 out of 10, Exceptional, (16)
"We had the most amazing time at this little cabin. Great trips are made by their location and this cabin has the most incredible location. We will definitely stay here again! "
House At The Point - Rustic Cottage on Ocean's Edge
Superb Location! 5min walk to town & EV charger port
Living room guest comfortable pull out bed/ couch

Superb Location! 5min walk to town & EV charger port

9.6 out of 10, Exceptional, (52)
"The cottage is a former "garage-barn" (2 floors) that's been lovingly re-crafted into a cottage that's nicely decorated with sea-themed and comfy decor. The locale is great if you'd like to ditch your car and walk to restaurants; and bike on nearby trails! We are only cautioning that IF you plan to cook your own meals, the kitchen set-up is on the 2nd floor with the bedroom. It's OK for short, quick meals (e.g microwaveable meals) you wish to prepare, but inconvenient for anything fancier. The...
Superb Location! 5min walk to town & EV charger port
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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Other property types in Islesboro

Island log home in Maine with ocean views
Exterior

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (66)
"A nice quiet spot tucked off the beaten path. All you need - coffee galore, a comfy bed and the space to relax. "
Island log home in Maine with ocean views
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
Interior

~ Peaceful And Quaint Family Cottage On An Island In Maine ~

9.8 out of 10, Exceptional, (44)
"We just finished a five-night stay at this property. Rustic is the perfect way to describe it along with offering modern amenities like 1 and 1/2 baths, a complete kitchen, washer dryer and great internet. It's a great secluded location with the General Store just a five minute drive away."
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
Trade Winds on the Bay
Interior

Trade Winds on the Bay

3.5 star property
8.2 out of 10, Very Good, (147)
"We got in very late. They had a lock box for us to get our keys after hours (texted us the code) and then checked on us the next day to make sure we made it safely. "
The price is SAR 394
SAR 468 total
includes taxes & fees
5 Jan - 6 January 2025
Trade Winds on the Bay
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.

Frequently asked questions

How much do cottages in Islesboro cost?
Expect to pay between and per night for cottages in Islesboro. No matter your budget, an ideal stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Islesboro?
Take your pick of 148 cottages in Islesboro. Whether you’re traveling with the kids or planning a weekend break with your pals, Expedia can help you find the ideal space to enjoy nature’s beauty.
Why book your cottage in Islesboro with Expedia?
Expedia has some terrific cottages in Islesboro, so get ready for a memorable stay close to nature. If you have a fixed budget, select how much you’re willing to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a pool. We’ll help you find the right place whatever your bank balance or plans.
How can I find cheap cottages in Islesboro?
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