Photo by Colleen Johnson

Holiday Rentals in Islesboro

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Check prices for these dates

Tonight
16 Feb - 17 Feb
Tomorrow
17 Feb - 18 Feb
Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar

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, (68)
"Cozy, quiet cabin with a good layout and nice view on the water. Easy check-in and check-out process. Host is very responsive. "
Island log home in Maine with ocean views
Trade Winds on the Bay
Reception

Trade Winds on the Bay

3.5 star property
8.2 out of 10, Very good, (172)
"Close to our venue and good value for the cost"
The price is €97
includes taxes & fees
17 Feb - 18 Feb
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, (164)
"Beautiful little cabin in the woods. The hosts were very friendly and accomodating."
The price is €194
includes taxes & fees
17 Feb - 18 Feb
Cozy Cabin By The Pond, Sleeps 2
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Marina

Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

9.2 out of 10, Wonderful, (70)
"Very spacious and cozy. We had a lovely time, just a few housekeeping issues. Other than that, the host was very quick to reply. We arrived to fresh flowers , a bottle of wine, chocolate ,coffee and a welcome note… "
The price is €609
includes taxes & fees
17 Feb - 18 Feb
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Point Lookout
Exterior

Point Lookout

3.0 star property
Point Lookout
Waterfront cottage with deep water dock, ocean front.
Exterior

Waterfront cottage with deep water dock, ocean front.

10.0 out of 10, Exceptional, (89)
"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.
House At The Point - Rustic Cottage on Ocean's Edge
Exterior

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
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

10.0 out of 10, Exceptional, (109)
"I was traveling with my 4 sisters. We enjoyed our stay very much. Hosts were very helpful with technical things and recommendations for places to eat and things to do. The cove on the ocean is great for sunrises and peaceful mornings. Beds were comfortable, Great place to wind down after a busy day!"
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
1812 Pierce House
Front of property

1812 Pierce House

3.5 star property
The price is €258
includes taxes & fees
17 Feb - 18 Feb
1812 Pierce House
Oceanfront retreat with sunrise views, screened porch, & deck
Dining

Oceanfront retreat with sunrise views, screened porch, & deck

9.8 out of 10, Exceptional, (34)
"Arrived to a clean, well decorated cottage. Smaller than expected for four adults. The view made up for any shortcomings. A small screened in porch, a deck, large flat granite rocks, the outside seating options are numerous. Best part of our day, coffee on the deck watching lobster boats, hearing loons, marveling at the sunrise. Be aware the use of the fireplace is prohibited. Would have been great on a rainy day. Location is good with proximity to Ellsworth for groceries, Bucklyn coffee in...
Oceanfront retreat with sunrise views, screened porch, & deck
Gorgeous Oceanfront Retreat on Penobscot Bay
Property grounds

Gorgeous Oceanfront Retreat on Penobscot Bay

9.8 out of 10, Exceptional, (58)
"Such a wonderful spot to sit relax and catch up! "
The price is €2,095
includes taxes & fees
17 Feb - 18 Feb
Gorgeous Oceanfront Retreat on Penobscot Bay
Gorgeous Waterfront Estate In Historic Bayside
Outdoor spa tub

Gorgeous Waterfront Estate In Historic Bayside

10.0 out of 10, Exceptional, (65)
"Our stay was perfect and we wouldn’t change a thing. Plenty of space as far as bedrooms and bathrooms go. So much common space to enjoy a fire, meals, and outdoor space. The beach is very wide during low tide and an added perk. Beds and pillows are very comfortable. We can’t wait to plan a return trip."
Gorgeous Waterfront Estate In Historic Bayside
Relaxing lodge in the woods
Exterior

Relaxing lodge in the woods

9.8 out of 10, Exceptional, (20)
"My grandson was so excited to see the bobcat in the yard. We’re no strangers to wild animals what a great home you have. Thanks for sharing your home with us. We would like to come back "
Relaxing lodge in the woods
Waterfront stay with scenic deck, grill, smart TVs, shore access - dog-friendly
Aerial view

Waterfront stay with scenic deck, grill, smart TVs, shore access - dog-friendly

9.6 out of 10, Exceptional, (18)
"Conveniently located near MMA. Nicely equipped, clean house. So appreciate that the house is pet friendly. Sometimes worry that pet friendly places will smell like dog ( pet friendly hotel rooms are the worst). Not this house. Very well maintained. Yard and rocky beach are beautiful. Very easy check-in. Loved the back deck, stargazing at night was beautiful. Lots of wildlife; saw deer every evening and an eagle. Thank you for a great family stay. "
Waterfront stay with scenic deck, grill, smart TVs, shore access - dog-friendly
Stay in this beautiful home: ocean views and access to midcoast Maine's charm!
Fridge, microwave, oven, stovetop

Stay in this beautiful home: ocean views and access to midcoast Maine's charm!

9.8 out of 10, Exceptional, (9)
"lovely little winer getaway. Cabin was everything we could have wanted. "
Stay in this beautiful home: ocean views and access to midcoast Maine's charm!
Comfortable, Close to Town Home, with Oceanview.
Interior

Comfortable, Close to Town Home, with Oceanview.

9.6 out of 10, Exceptional, (66)
"Great management, very clean, had everything in the kitchen, comfortable beds, even a pen for a dog. The sky was beautiful at night. It was very quiet. We were very close to hiking trails and the lighthouse. We had a nice time at Christmas."
The price is €343
includes taxes & fees
17 Feb - 18 Feb
Comfortable, Close to Town Home, with Oceanview.
Cozy cottage -Close to Downtown Camden!
2 bedrooms, WiFi, bed sheets

Cozy cottage -Close to Downtown Camden!

2.0 star property
9.6 out of 10, Exceptional, (5)
"A very clean and sweet little place no where near walking to downtown Camden"
The price is €481
includes taxes & fees
17 Feb - 18 Feb
Cozy cottage -Close to Downtown Camden!
Peacefull house on the water
Beach

Peacefull house on the water

9.6 out of 10, Exceptional, (26)
"This cozy home had everything we needed for our Thanksgiving getaway. It's beautifully updated, warm, comfortable, and centrally located to what we wanted to do. It's located in a quiet, riverfront area for a peaceful stay. Only the turkeys, squirrels, and an occasional lobster boat to get your attention. Just perfect. I highly recommend this property."
Peacefull house on the water
Apt 1 Studio apartments in downtown Stonington
Interior

Apt 1 Studio apartments in downtown Stonington

9.8 out of 10, Exceptional, (59)
"My husband and I stayed 2 nights here on our 2 week road trip and I cannot express how happy we were with our stay. The apartment was super clean and cute, the town was like a Hallmark movie. We would definitely love to come stay for a longer visit in the future!"
The price is €202
includes taxes & fees
18 Feb - 19 Feb
Apt 1 Studio apartments in downtown Stonington
Bring the Family - Private Balconies - Water Views
Interior

Bring the Family - Private Balconies - Water Views

10.0 out of 10, Exceptional, (47)
"This apartment was just beautiful. A unique lay out, spacious, two decks, jacuzzi tub, etc. THE VIEW IS JUST BREATHTAKING. Excellent spot with picturesque ocean views in our incredible state. "
Bring the Family - Private Balconies - Water Views
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, (68)
"Cozy, quiet cabin with a good layout and nice view on the water. Easy check-in and check-out process. Host is very responsive. "
Island log home in Maine with ocean views
Trade Winds on the Bay
Reception

Trade Winds on the Bay

3.5 star property
8.2 out of 10, Very good, (172)
"Close to our venue and good value for the cost"
The price is €97
includes taxes & fees
17 Feb - 18 Feb
Trade Winds on the Bay
The Country Inn at Camden Rockport
Lobby

The Country Inn at Camden Rockport

2.5 star property
9.6 out of 10, Exceptional, (1002)
"This place was amazing. It was the cleanest hotel we have ever stayed in. Breakfast was a plus!"
The price is €124
includes taxes & fees
2 Mar - 3 Mar
The Country Inn at Camden Rockport
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 9 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 Camden Hills State Park 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.