Photo by Colleen Johnson

Search Vacation Homes 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 457 Vacation Homes in Islesboro with updated reviews, rates, and availability.

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

9.2 out of 10, Wonderful, (15)
"This home is a gem. We had a great time! The view from the kitchen window is just beautiful. "
Stay in this beautiful home: ocean views and access to midcoast Maine's charm!

2 Bedroom Close to Town Home

9.2 out of 10, Wonderful, (27)
"Very clean and nice property as advertised."
The price is SAR 431
SAR 981 total
includes taxes & fees
1 Jun - 2 Jun
2 Bedroom Close to Town Home

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

10.0 out of 10, Exceptional, (15)
"Amazing cozy cottage with a breath taking view!"
Oceanfront home on 6 acres with multi-level deck & spectacular view

Oceanfront retreat with sunrise views, screened porch, & deck

9.8 out of 10, Exceptional, (34)
"Beautiful house with even better view of the coast/ocean! It’s hard to beat this house for the price and you won’t be disappointed! Would stay here again if given the chance."
Oceanfront retreat with sunrise views, screened porch, & deck

Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

9.8 out of 10, Exceptional, (108)
"A little out of town in a cove overlooking the ocean. Nice place to relax on the patio and a little walk down to the private beach. Rockland is a nice town - plenty of places to stroll and places to eat - a good place as a base for our trip. "
Oceanfront,Unobstructed Views Private Onsite ocean access to a small sandy beach

Secluded lakefront home with patio & firepit, fast WiFi, wood stove & W/D

9.4 out of 10, Exceptional, (29)
"Great spot to relax, kayak, and spend some good family time! Close enough to Acadia that we went every day."
Secluded lakefront home with patio & firepit, fast WiFi, wood stove & W/D

Relaxing lodge in the woods

9.8 out of 10, Exceptional, (20)
"Beautiful place to stay"
Relaxing lodge in the woods

In-town, coastal + relaxing in Rockland

10.0 out of 10, Exceptional, (23)
"The unit was impeccable as was the location: just 100 yards from Rockland Harbor and the harbor view walk. The hose was immaculate and the kitchen had everything you need to cook in. We are in our early 70s and would highly recommend a stay here. We met the owners, Jim and Wayne, who were delightful "
The price is SAR 788
SAR 1,913 total
includes taxes & fees
5 May - 6 May
In-town, coastal + relaxing in Rockland

Lovely Waterfront Owls Head Home w/ Own Beach

10.0 out of 10, Exceptional, (50)
"This house was comfortable and had an amazing view. The location was perfect!"
Lovely Waterfront Owls Head Home w/ Own Beach

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 SAR 825
SAR 1,823 total
includes taxes & fees
17 May - 18 May
Waterfront Getaway Near Acadia w/ Spectacular View

Charming Sandy Point Home

9.8 out of 10, Exceptional, (53)
"We were family of 5 with adult kids staying at c"
Charming Sandy Point Home

Remodeled Home w/ River Views in Frankfort!

Remodeled Home w/ River Views in Frankfort!

Comfortable & Charming 2-bedroom barn in peaceful Brooksville with Waterfront

10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed our stay in Brooksville. The property is beautiful and quiet, but close to local hikes. The beds were super comfortable and we loved the chefs kitchen, which is actually appointed so you can make meals easily. The property was very clean and the WiFi fast (we had to work remotely one day). Host was easy to communicate with and flexible when we needed to alter checkout. We will definitely be back when it is warmer, the path to the water would be wonderful then"
Comfortable & Charming 2-bedroom barn in peaceful Brooksville with Waterfront

Cozy cottage in woodland setting near to hiking biking and lakes

10.0 out of 10, Exceptional, (5)
"Beautiful home. We slept great in the super comfy beds and peaceful setting. We settled in and wish we could stay for another week. Conveniently located near hiking and town. A perfect stay, we’ll be back!"
Cozy cottage in woodland setting near to hiking biking and lakes

Idyllic Washington Retreat w/ Fire Pit & Yard

9.2 out of 10, Wonderful, (12)
"We stayed here because it was outside of Augusta and centered between the coast line, Moosehead Lake, and the scenic NatIonal Park."
Idyllic Washington Retreat w/ Fire Pit & Yard

Charming 3-bedroom house with AC and WiFi in Thomaston

Charming 3-bedroom house with AC and WiFi in Thomaston

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 SAR 769
SAR 1,472 total
includes taxes & fees
4 May - 5 May
Comfortable, Close to Town Home, with Oceanview.

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (69)
"We had a very cozy and comfortable stay here over the christmas holiday! We had everything we needed to hunker down for a few days. Would absolutely stay here again. "
Island log home in Maine with ocean views

Historic charming pet and family friendly 3-bedroom farmhouse in Camden.

9.2 out of 10, Wonderful, (5)
"Kate was a wonderful host. There were so many little things that she did that made it feel so welcoming and a need for nothing. The garland on the banister was a pefect holiday decoration. Comfortable beds, toiletries if they were needed. Very pleased."
Historic charming pet and family friendly 3-bedroom farmhouse in Camden.

Gorgeous Waterfront Estate In Historic Bayside

10.0 out of 10, Exceptional, (65)
"It was a beautiful home and they had everything you needed to enjoy your stay!"
Gorgeous Waterfront Estate In Historic Bayside
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.
Don't see what you're looking for?
See all available properties in Islesboro
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Islesboro

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (69)
"We had a very cozy and comfortable stay here over the christmas holiday! We had everything we needed to hunker down for a few days. Would absolutely stay here again. "
Island log home in Maine with ocean views

Trade Winds on the Bay

4.0 star property
8.2 out of 10, Very Good, (209)
"We stay here often, it’s beautiful staff is great, Pool is great! "
The price is SAR 436
SAR 475 total
includes taxes & fees
11 May - 12 May
Trade Winds on the Bay

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (167)
"Beautiful little cabin in the woods. The hosts were very friendly and accomodating."
The price is SAR 450
SAR 744 total
includes taxes & fees
4 May - 5 May
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.