Photo by Colleen Johnson

Islesboro Holiday Rentals

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Holiday Rentals in Islesboro

Island log home in Maine with ocean views
Fridge, microwave, oven, stovetop
Island log home in Maine with ocean views
10.0 out of 10, Exceptional, (64)
"The cabin was perfect. Wedding weekend for a friend on the island. Cabin was perfect spot for family - comfortable, clean and close to all we needed. "
Island log home in Maine with ocean views
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
Property grounds
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
9.8 out of 10, Exceptional, (43)
"Cabin was welcoming, very clean, relaxful, and very quiet. The ocean views from the porches were spectacular. The stairs to get to the beach were scary but worth it. Over-all the stay was memorable. "
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
Trade Winds on the Bay
Reception
Trade Winds on the Bay
3.0 star property
7.8 out of 10, Good, (104)
"I like everything "
The price is AU$299
includes taxes & fees
3 Oct - 4 Oct
Trade Winds on the Bay
Cozy Cabin By The Pond, Sleeps 2
Exterior
Cozy Cabin By The Pond, Sleeps 2
10.0 out of 10, Exceptional, (150)
"Our stay a the Cozy Cabin was just what we needed. Thank you and hope to do it again next year!"
The price is AU$310
includes taxes & fees
14 Oct - 15 Oct
Cozy Cabin By The Pond, Sleeps 2
Cozy Cabin on Blue Hill Farm
Interior
Cozy Cabin on Blue Hill Farm
9.8 out of 10, Exceptional, (23)
"We enjoyed our stay very much. If it had been warm enough to enjoy all of our meals outside that would have been wonderful. We didn’t plan or pack for any rain but when it poured for a solid day, we were thankful for the cabin’s shelter and wifi and umbrella when we went out. Although we brought an infant and a 2.5yo, I wouldn’t necessarily recommend this property for such little/young kids unless you’re prepared for spotting them up and down the ladder. We loved the hanging indoor swing and our...
Cozy Cabin on Blue Hill Farm
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
On the beach, sun-loungers
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
9.8 out of 10, Exceptional, (105)
"Centrally located - 2 hrs from the Portland airport and 2 hours from Acadia National Park. Alex is very warm and he and Siobahn were very responsive."
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach
Waterfront cottage with deep water dock, ocean front.
Exterior
Waterfront cottage with deep water dock, ocean front.
9.8 out of 10, Exceptional, (80)
"We stayed two weeks at this property and very much enjoyed it. The cottage is near the Belfast rail trail and we walked on this every day. We liked that the location felt very private yet it was only about a mile walk on the rail trail to Belfast harbor. The other great thing about this property is proximity to the Passagassawakeag River. It's just at the backside of the property and the owners have a very nice dock that was available for our use. The cottage had everything we needed and was...
Waterfront cottage with deep water dock, ocean front.
Private cabin on the Maine coast
Exterior
Private cabin on the Maine coast
9.4 out of 10, Exceptional, (18)
"Cabin was comfortable and clean - just as advertised!"
The price is AU$478
includes taxes & fees
28 Oct - 29 Oct
Private cabin on the Maine coast
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
On the beach, sun-loungers
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
9.8 out of 10, Exceptional, (108)
"Such a beautiful property! Our flight got a bit late and Alex and Siobhán were gracious and kind. They met us with the keys and went over the information needed. Because it was dark when we arrived, we were so amazed to see the beautiful views when we awoke. We were close to shops and amazing restaurants. I would definitely recommend!"
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
Cozy Cottage on Cat Cove w/ Wraparound Deck!
Fridge, microwave, stovetop, coffee/tea maker
Cozy Cottage on Cat Cove w/ Wraparound Deck!
7.4 out of 10, Good, (12)
"Grill did not work. "
Cozy Cottage on Cat Cove w/ Wraparound Deck!
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
TV, books, streaming services
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
9.6 out of 10, Exceptional, (14)
"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
Overlook Cottage, Toddy Pond!
Beach nearby
Overlook Cottage, Toddy Pond!
9.0 out of 10, Wonderful, (42)
"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!
Oceanfront retreat with sunrise views, screened porch, & deck
Property grounds
Oceanfront retreat with sunrise views, screened porch, & deck
9.8 out of 10, Exceptional, (30)
"A beautiful cottage on the water that was well appointed. It was a perfect place for our visit to Maine. The only disappointment was we were never connected to WiFi."
Oceanfront retreat with sunrise views, screened porch, & deck
Visit for Fall Foliage AND the Beach
Property grounds
Visit for Fall Foliage AND the Beach
9.8 out of 10, Exceptional, (65)
"It was a nice change."
Visit for Fall Foliage AND the Beach
Secluded house just minutes away from Deer Isle/Stonington villages and beaches!
Outdoor dining
Secluded house just minutes away from Deer Isle/Stonington villages and beaches!
10.0 out of 10, Exceptional, (41)
"Delightful house in a peaceful and quiet setting. The house is immaculate, comfortable, and full of regional decorations. Appliances are outstanding. The large deck overlooks a beautiful lawn. "
Secluded house just minutes away from Deer Isle/Stonington villages and beaches!
Batten's ReTreat (formerly Close Call Cottage)
Property grounds
Batten's ReTreat (formerly Close Call Cottage)
7.2 out of 10, Good, (9)
"Very easy to use the cottage. Restful and quiet. Enjoyed it every day and night."
Batten's ReTreat (formerly Close Call Cottage)
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
View from property
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
9.8 out of 10, Exceptional, (64)
"Beautiful and very cozy stay close to everything you’d want to do, hike, explore, enjoy. Whirlpool jets in the tub was great after a long hike and we loved stargazing on the terrace. "
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres
2 bedrooms, desk, free Internet, bed sheets
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres
9.8 out of 10, Exceptional, (72)
"WE had a great time at the cabin, it had everything we need for our 4 nights stay. Only 15min away from Belfast ME."
Rustic Searsport Cabin: Loft + Sunroom on 10 Acres
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Property grounds
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
9.2 out of 10, Wonderful, (66)
"Our family really enjoyed their stay at this home while in town for a wedding, and it felt great to have space for everyone! The cousins shared the double bed rooms and parents got the main rooms. Two bathrooms, one being on-suite, was a bit of a challenge when it came time to get ready for bed, get ready in the morning and get ready for a wedding (also, one low quality hair dryer for the entire home and nearly empty soap bottles when we arrived) but having a well stocked kitchen and dining...
The price is AU$1,090
includes taxes & fees
27 Oct - 28 Oct
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Waterfront Getaway Near Acadia w/ Spectacular View
On the beach, beach towels
Waterfront Getaway Near Acadia w/ Spectacular View
10.0 out of 10, Exceptional, (12)
"located gave easy access to explore the area"
The price is AU$609
includes taxes & fees
3 Oct - 4 Oct
Waterfront Getaway Near Acadia w/ Spectacular View
Don't see what you're looking for?
See all available properties in Islesboro
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 types of properties in Islesboro you may be interested in

Island log home in Maine with ocean views
Fridge, microwave, oven, stovetop
Island log home in Maine with ocean views
10.0 out of 10, Exceptional, (64)
"The cabin was perfect. Wedding weekend for a friend on the island. Cabin was perfect spot for family - comfortable, clean and close to all we needed. "
Island log home in Maine with ocean views
The Country Inn at Camden Rockport
Exterior
The Country Inn at Camden Rockport
2.5 star property
9.4 out of 10, Exceptional, (1004)
"Very spacious pleasant rooms. Very nice breakfast and near excellent dining spots. One negative for me: all the many pillows were large and hard. How about at least one soft."
The price is AU$235
includes taxes & fees
29 Oct - 30 Oct
The Country Inn at Camden Rockport
Belfast Harbor Inn
Indoor pool, seasonal outdoor pool
Belfast Harbor Inn
3.5 star property
9.6 out of 10, Exceptional, (1002)
"Breakfast staff were very accommodating with a good attitude. Nice view of the harbor if room on back side. My room had a slight odor, possibly some leftover construction odors. Very attractive building and room. "
The price is AU$235
includes taxes & fees
28 Oct - 29 Oct
Belfast Harbor Inn
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

Can I find a holiday rental in Islesboro?

Yes, there are holiday rentals close to the most popular sights in Islesboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Islesboro has to offer?

Island log home in Maine with ocean views: This highly rated holiday home rental in Islesboro offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Islesboro?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Islesboro stay.

What’s there to see and do in Islesboro?

While exploring the area, visit family-friendly sights like Penobscot Marine Museum, or get outside and enjoy nature at Warren Island State Park. Lincolnville Ferry Terminal and Lincolnville Beach are a couple of places you'll find in the wider area.

What’s a holiday rental in Islesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islesboro. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for families.