Photo by Colleen Johnson

Holiday Rentals in Islesboro

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Islesboro

Fridge, microwave, oven, stovetop
Island log home in Maine with ocean views
10.0 out of 10, Exceptional, (54)
"My wife and I thought the property was fantastic. It was well maintained and very clean. If you want a nice quiet getaway I would highly recommend this place."
Island log home in Maine with ocean views
Property grounds
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
9.8 out of 10, Exceptional, (38)
"Pros: Quiet. This is it if you are looking for quiet. The cottage: The glassed-in porch is the star. The windows open too. The kitchen is updated and a pleasure to cook in. The living room is very cozy at night. There was a musky smell when we 1st arrived, but went away quickly once all windows were open and never came back, but then again the windows were open the whole vacation. Cons: The view will be obstructed soon if the owner doesn't cut down some small trees, it seems without affecting...
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
Panoramic Suite, 1 King Bed with Sofa bed, Balcony, Harbour View
Trade Winds on the Bay
3.0 star property
7.6 out of 10, Good, (39)
"Like that we can walk to everything we’ll just about, didnt like the construction that was going on at the hotel, no restaurant in hotel and bit small bathrooms but everything else was wonderful "
The price is €134
includes taxes & fees
24 May - 25 May
Trade Winds on the Bay
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
Cozy Cabin By The Pond, Sleeps 2
10.0 out of 10, Exceptional, (128)
"I had a wonderful stay at the cozy cabin. John and Barbara couldn't have been more helpful or welcoming, and the cabin itself was perfect: clean, bright, and thoughtfully arranged. It had exactly what I needed and nothing I didn't, which meant I could turn my attention to relaxing. Highly recommend!"
The price is €201
includes taxes & fees
30 May - 31 May
Cozy Cabin By The Pond, Sleeps 2
Oven, stovetop, coffee/tea maker, electric kettle
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
Beach
Oceanfront,Unobstructed Ocean Views, Onsite ocean access to a small sandy beach
10.0 out of 10, Exceptional, (88)
"Maine is spectacular in mid-October. The Primrose Apartment was the perfect location to see the colorful leaves, visit lighthouses and enjoy all both Rockland and Camden have to offer. Alex and Siobhan were gracious, thoughtful and kind hosts. The view of Glen Cove from both the kitchen window and the deck is stunning. The Primrose was the perfect property and location for our stay."
Oceanfront,Unobstructed Ocean Views, Onsite ocean access to a small sandy beach
Exterior
Waterfront cottage with deep water dock, ocean front.
9.8 out of 10, Exceptional, (67)
"We had a great stay at the Belfast cottage. It was clean & well equipped with everything we needed. The owner Jon was a pleasure. Enjoyed the back patio at night. We walked to town on the rail trail behind the house. Belfast is a great town ."
Waterfront cottage with deep water dock, ocean front.
On the beach, sun-loungers
Oceanfront, Onsite Ocean Access to a small beach. Fantastic Ocean & Island Views
9.8 out of 10, Exceptional, (87)
"We renewed our wedding vows at Children’s Chapel. The area is beautiful, beach is amazing, there is a rock on the beach that has dates and names carved all over it from the 1800’s. The host was GREAT Alex told us stories and let us hear his “Alabama accent” LOL. I could’ve talked to him all day. We had a great trip and plan on coming back."
Oceanfront, Onsite Ocean Access to a small beach. Fantastic Ocean & Island Views
Fridge, microwave, stovetop, coffee/tea maker
Cozy Cottage on Cat Cove w/ Wraparound Deck!
7.4 out of 10, Good, (8)
"Super cute cabin RIGHT on the lake. Wish it would have been warmer during our stay. The cabin is very secluded and quiet with a fire pit outside for relaxing. Be sure to have the directions ready from the property manager as your GPS won't pick the address up."
Cozy Cottage on Cat Cove w/ Wraparound Deck!
Exterior
Private cabin on the Maine coast
9.0 out of 10, Wonderful, (2)
"Great stay!"
The price is €275
includes taxes & fees
23 May - 24 May
Private cabin on the Maine coast
Property grounds
Stay at the Beach! - Private Balcony - Sunrise
9.8 out of 10, Exceptional, (55)
"We thoroughly enjoyed our stay here. It's very comfortable, has laundry facility and the host was in communicate when we called. We'll be back to stay here in the future!"
Stay at the Beach! - Private Balcony - Sunrise
Interior
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
9.8 out of 10, Exceptional, (6)
"Had the good old field of what we always called a "camp." Kitchen was well stocked with utensils and glassware, etc. The lobster processing facility made for a bit of noise and a pretty steady stream of traffic. A lot of trucks, from pickups to semis coming in and out. Didn't really bother us a whole lot but it might bother other people. Overall the view of the water was pretty nice except for the power lines and there's not much that can be done about that. Have to have electricity after all."
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Property grounds
Secluded house just minutes away from Deer Isle/Stonington villages and beaches!
10.0 out of 10, Exceptional, (27)
"The house was beautiful and exactly what we needed. Mike and Rachael were fantastic."
Secluded house just minutes away from Deer Isle/Stonington villages and beaches!
View from property
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
9.8 out of 10, Exceptional, (59)
"This home was even better than the pictures! The space is so cozy and decorated beautifully. The hosts left a huge bouquet of fresh flowers for us along with bread, chocolates, and jams. Checking in and out was super easy and the home had all the accommodations you could need. Definitely will be back!"
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Property grounds
Oceanfront retreat with sunrise views, screened porch, & deck
9.8 out of 10, Exceptional, (16)
"We visited the first week in November. The property is gorgeous, but the listings between VRBO and Vacasa (a third party that handles the actual communication for check in and such) have huge discrepancies about being dog friendly. This caused significant stress when we arrived as we had to find the original listing saying we could bring our small dog. I would definitely recommend the property, but just be sure you keep track of what you are agreeing to. Also, the bedrooms were warm enough...
Oceanfront retreat with sunrise views, screened porch, & deck
Fridge, microwave, oven, stovetop
Cabin with deck, grill & fire table on 10 private acres - near Crescent Beach
8.0 out of 10, Very good, (4)
"All of the smoke detectors need the batteries replaced. I bought batteries and replaced most of them but there was one still incessantly beeping. The house was great. We will book it again The"
Cabin with deck, grill & fire table on 10 private acres - near Crescent Beach
Property grounds
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
9.2 out of 10, Wonderful, (60)
"This house was awesome for our family to gather for my daughter's wedding. The wedding party got ready in the beautiful living room and there was plenty of room. Walkable to town and the wedding venue made this spot ideal. Seamless check in and check out."
The price is €883
includes taxes & fees
16 Jun - 17 Jun
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
On the beach, sun-loungers
Oceanfront, Unobstructed Views, Onsite Access to the water & small sandy beach.
10.0 out of 10, Exceptional, (104)
"Lovely property and the hosts could not be more accommodating. Very helpful and friendly. The view is amazing."
Oceanfront, Unobstructed Views, Onsite Access to the water & small sandy beach.
Exterior
Owls Head Village Post Office
10.0 out of 10, Exceptional, (130)
"Magical for us and our 10yo, who started asking to come back about 2 minutes after arriving."
Owls Head Village Post Office
Property grounds
Close Call - A Charming Oceanfront Cottage
6.6 out of 10, (7)
"Wonderful retreat. I enjoyed watching the tide, the birds, and the walk through the adjacent preserve."
Close Call - A Charming Oceanfront Cottage
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.

Other types of properties in Islesboro you may be interested in

Fridge, microwave, oven, stovetop
Island log home in Maine with ocean views
10.0 out of 10, Exceptional, (54)
"My wife and I thought the property was fantastic. It was well maintained and very clean. If you want a nice quiet getaway I would highly recommend this place."
Island log home in Maine with ocean views
Exterior
The Country Inn at Camden Rockport
2.5 star property
9.4 out of 10, Exceptional, (1000)
"Friendly staff, clean and beautiful!"
The price is €140
includes taxes & fees
27 May - 28 May
The Country Inn at Camden Rockport
1 King Bed w/Balcony, 3rd Floor, No Pets | View from room
Camden Riverhouse Hotel
2.5 star property
9.4 out of 10, Exceptional, (711)
"We loved our stay. Kaitlin was a wonderful host. The dining crew was great too. A nice hotel and lots of small amenities such as a fire pit and s’mores. "
The price is €140
includes taxes & fees
23 May - 24 May
Camden Riverhouse Hotel
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.

Everything you need to know about Islesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Islesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Islesboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Islesboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Islesboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islesboro holiday rentals we have selected for you start as low as €134 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Islesboro rentals

At Expedia, we put the best Islesboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Islesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Islesboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Islesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Beach and Pitcher Pond 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.

Recent reviews of Islesboro properties
Expedia verified reviews

Colonial Gables Oceanfront Village

Colonial Gables Oceanfront Village

5/5 Excellent
"Absolutely loved it!"
A verified traveller stayed at Colonial Gables Oceanfront Village
Posted 22 hours ago
Colonial Gables Oceanfront Village