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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 360 Vacation Homes in Islesboro with updated reviews, rates, and availability.

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

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!
Oceanfront home on 6 acres with multi-level deck & spectacular view

Oceanfront home on 6 acres with multi-level deck & spectacular view

10.0 out of 10, Exceptional, (14)
"Amazing cozy cottage with a breath taking view!"
Oceanfront home on 6 acres with multi-level deck & spectacular view
Charming Camden Home in a quiet and convenient location
Back yard and Deck

Charming Camden Home in a quiet and convenient location

2.0 star property
Charming Camden Home in a quiet and convenient location
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
located on Camden Harbor , we sit behind the Marina. Walk to everything !

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… "
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Gorgeous Oceanfront Retreat on Penobscot Bay
Estate on the sea. The house has been restored to its original "shingled" look.

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 AED 4,959
AED 7,875 total
includes taxes & fees
24 Feb - 25 Feb
Gorgeous Oceanfront Retreat on Penobscot Bay
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
Small beach area located behind the house

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
Comfortable, Close to Town Home, with Oceanview.
Miscellaneous

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 AED 643
AED 1,289 total
includes taxes & fees
24 Feb - 25 Feb
Comfortable, Close to Town Home, with Oceanview.
Lovely Waterfront Owls Head Home w/ Own Beach
Owls Head Vacation Rental | 3BR | 2BA | Stairs Required | 2,560 Sq Ft

Lovely Waterfront Owls Head Home w/ Own Beach

10.0 out of 10, Exceptional, (48)
"The house is lovely, great location and situation. The shore just below the house is rocky and charming, but requires caution descending to it (in the winter anyway). Sunrise over the south end of Monroe Island is just gorgeous. Views from every room. The kitchen is great, and the most generously supplied with cookware and dishes that I've ever seen in a rental. Super."
Lovely Waterfront Owls Head Home w/ Own Beach
Relaxing lodge in the woods
Room

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
Luxury Coastal Estate w/ Private Beach Access, 45 minutes from Acadia
Looking out towards Maine coastline during fall, 5 minutes walk to quiet beach.

Luxury Coastal Estate w/ Private Beach Access, 45 minutes from Acadia

10.0 out of 10, Exceptional, (5)
"Exactly what we were looking for. The house and the surrounding area is beautiful! We definitely will return back soon. Thanks! "
Luxury Coastal Estate w/ Private Beach Access, 45 minutes from Acadia
Journeys End Loft
Interior

Journeys End Loft

9.8 out of 10, Exceptional, (20)
"Comfortable, convenient to family we were visiting."
Journeys End Loft
2 Bedroom Close to Town Home
Exterior

2 Bedroom Close to Town Home

9.0 out of 10, Wonderful, (26)
"Our primary objective was a clean cost-effective one night stay for a road trip through New England. This was right on the road, which was convenient but a little bit noisy at night."
The price is AED 386
AED 917 total
includes taxes & fees
24 Feb - 25 Feb
2 Bedroom Close to Town Home
Charming Cottage in Quaint Coastal Bayside, Maine with Waterview
Exterior

Charming Cottage in Quaint Coastal Bayside, Maine with Waterview

2.0 star property
10.0 out of 10, Exceptional, (12)
"This was a perfect, toasty warm, place for family to stay over the Christmas holiday. The open floor plan on the first floor is wonderful for communicating. The one year old enjoyed walking around this area. We enjoyed the big dinning table for meals, board games, and wrapping gifts. The beds were very comfortable. Two of the bedrooms have a water view in winter! The property managers are exceptionally attentive. They went above and beyond coming first thing in the morning to shovel snow!"
Charming Cottage in Quaint Coastal Bayside, Maine with Waterview
Sweet Home with Stunning Water Views
The Arey House

Sweet Home with Stunning Water Views

9.0 out of 10, Wonderful, (18)
"We stayed here for almost two weeks in late June/early July. The location was great for our purposes (we come to the area each summer to see family who live just minutes away), and we enjoyed walks with our preschooler down to the little beach to hunt for sea glass. We also liked the large yard and beautiful newer deck for added enjoyment outside - the view is lovely. The house is an older farmhouse with some updates; we expected and enjoyed the more vintage touches. The upstairs can get hot,...
Sweet Home with Stunning Water Views
Sunset river 3-bedroom house in amazing South Thomaston, Maine
Property grounds

Sunset river 3-bedroom house in amazing South Thomaston, Maine

2.0 star property
Sunset river 3-bedroom house in amazing South Thomaston, Maine
The RiverView
Exterior

The RiverView

9.2 out of 10, Wonderful, (12)
"The house was very clean, comfortable and quiet. We had everything we needed for a great getaway. The location was perfect for everything we wanted to do - would highly recommend!"
The price is AED 551
AED 1,121 total
includes taxes & fees
24 Feb - 25 Feb
The RiverView
Breathtaking views, total relaxation, do as much or as little as you choose
Little island, mussel ridge channel, all the boats go by the house

Breathtaking views, total relaxation, do as much or as little as you choose

9.8 out of 10, Exceptional, (82)
"My wife and I enjoyed our stay in Owls Head. It was perfect for us. Hiking trails nearby and good seafood not far away"
Breathtaking views, total relaxation, do as much or as little as you choose
Ground-floor duplex with WiFi & W/D - walk to river and downtown

Ground-floor duplex with WiFi & W/D - walk to river and downtown

9.0 out of 10, Wonderful, (14)
"This place is very clean and the rooms are large. I enjoyed the walk down to the water, which is close by. Kitchen was well stocked. I, too, felt a railing on the stairs would be helpful. I am new to the Vacasa connection, so that took some learning, but all went well. "
Ground-floor duplex with WiFi & W/D - walk to river and downtown
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Property grounds

Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

10.0 out of 10, Exceptional, (3)
"The house is new, absolutely immaculate and filled with light. The fully equipped kitchen was a joy to work in. The proximity to both Belfast and Camden was a huge plus. Our 2 dogs loved the open grassy field! A very friendly neighborhood too."
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Island log home in Maine with ocean views
Exterior

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
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, (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
Interior

Trade Winds on the Bay

3.5 star property
8.2 out of 10, Very Good, (176)
"Close to our venue and good value for the cost"
The price is AED 344
AED 375 total
includes taxes & fees
24 Feb - 25 Feb
Trade Winds on the Bay
Cozy Cabin By The Pond, Sleeps 2
Welcome to the Cozy Cabin

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (165)
"My husband, dog and I had a wonderful, quiet stay. The kitchen had everything we needed for meals and the wifi was perfect for binge watching our favorite tv shows on our laptop. I hurt my back just as we were leaving to drive the 3 hours from home to the cabin. When we arrived I was still hurting. John gave me a heating pad and ice pack to use, which was very nice and super helpful. "
The price is AED 441
AED 729 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Cabin By The Pond, Sleeps 2
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.