Islesboro Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Islesboro holiday rentals

1 bedroom, bed sheets

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Lincolnville
8.0 out of 10, Very good, (11 reviews)
"The cabin is exactly as advertised. The dogs were happy there and we enjoyed our stay. "
United States
Becki C.
The price is HK$599
HK$1,208 total
includes taxes & fees
17 May - 18 May
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Property grounds

Cozy Cabin By The Pond, Sleeps 2

Cozy Cabin By The Pond, Sleeps 2
Waldo
10.0 out of 10, Exceptional, (204 reviews)
"Very peaceful and cozy cabin! We had a wonderful weekend getaway and will definitely be back! "
United States
Johanna W.
The price is HK$1,135
HK$1,809 total
includes taxes & fees
17 May - 18 May
Cozy Cabin By The Pond, Sleeps 2
Terrace/patio

SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature

SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Penobscot
10.0 out of 10, Exceptional, (8 reviews)
"All was fabulous!!!"
United States
Maria M.
The price is HK$1,755
HK$3,560 total
includes taxes & fees
19 May - 20 May
SeaRiver Cabin on the Bagaduce, Kayaks Included. Seals, Wildlife, Birds & Nature
Interior

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (46 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is HK$939
HK$2,099 total
includes taxes & fees
28 May - 29 May
2 Bedroom Close to Town Home
Miscellaneous

The Lewis R. French- Inn on the Harbor

The Lewis R. French- Inn on the Harbor
Stonington
9.2 out of 10, Wonderful, (10 reviews)
"Made wonderful memories and really enjoyed the beautiful oceanfront town of Stonington."
United States
Elizabeth P.
The price is HK$765
HK$1,217 total
includes taxes & fees
19 May - 20 May
The Lewis R. French- Inn on the Harbor
Terrace/patio

Starry Artsy Garage Loft

Starry Artsy Garage Loft
Sedgwick
9.8 out of 10, Exceptional, (28 reviews)
"Absolutely great stay. Wonderful home, wonderful host! I will be keeping this place in mind for when I come back to Maine! "
United States
Kellee M.
The price is HK$1,050
HK$2,458 total
includes taxes & fees
17 May - 18 May
Starry Artsy Garage Loft
Dining

Cheerful Two Bedroom Cabin - 10 minutes to Camden!

Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
10.0 out of 10, Exceptional, (13 reviews)
"This is a great place, nice and quiet, very clean and cozy. Loved it here!!"
United States
Lorna W.
The price is HK$1,376
HK$3,138 total
includes taxes & fees
15 May - 16 May
Cheerful Two Bedroom Cabin - 10 minutes to Camden!
Exterior

Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (17 reviews)
"We had never stayed in a yurt before and this one had everything you need. We ate breakfast out on the deck and enjoyed the scenery. We had a really nice time!"
United States
Karen I.
The price is HK$1,135
HK$1,781 total
includes taxes & fees
20 May - 21 May
Dome 1 - Luxury Dome at Come Spring Farm
Interior

Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
The price is HK$955
HK$3,155 total
includes taxes & fees
26 May - 27 May
Rustic Retreat Across From Lake; Family Friendly!
Lobby sitting area

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (384 reviews)
"Clean room and friendly staff "
United States
John
The price is HK$778
HK$848 total
includes taxes & fees
17 May - 18 May
Trade Winds on the Bay
Smart TV

Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.4 out of 10, Exceptional, (32 reviews)
"Great stay and host was very responsive with a forgotten item. "
United States
Yvonne T.
The price is HK$979
HK$2,099 total
includes taxes & fees
17 May - 18 May
Peaceful, Centrally Located Home with Seasonal River Views
Interior

Bayside vista

Bayside vista
Bucksport
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay in Bucksport. The apartment was comfortable, clean and had everything we needed - and the view could not be beat! "
United States
Allison M.
The price is HK$1,416
HK$2,969 total
includes taxes & fees
19 May - 20 May
Bayside vista
Property grounds

Waterfront Getaway Near Acadia w/ Spectacular View

Waterfront Getaway Near Acadia w/ Spectacular View
Deer Isle
10.0 out of 10, Exceptional, (20 reviews)
"Great location with everything we needed."
United States
Thomas P.
The price is HK$1,219
HK$3,189 total
includes taxes & fees
15 May - 16 May
Waterfront Getaway Near Acadia w/ Spectacular View
Fridge, microwave, oven, stovetop

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (29 reviews)
"Very cute house that was fully equipped for our stay. Great location for touring around Maine to see the sights. Communication was excellent with the host and we would definitely stay here again!"
United States
Elisabeth C.
The price is HK$1,092
HK$2,812 total
includes taxes & fees
18 May - 19 May
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Exterior

Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly

Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
Lincolnville
10.0 out of 10, Exceptional, (10 reviews)
"Great owner and quick night stay. "
United States
Jeanean W.
The price is HK$1,389
HK$1,728 total
includes taxes & fees
31 May - 1 Jun
Pine Grove Cottages : Cottage 6 - Studio Cottage - Pet Friendly
Exterior

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
Rockport
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,002
HK$1,980 total
includes taxes & fees
25 May - 26 May
Romantic Coastal Escape near Harbor
WiFi

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is HK$1,566
HK$2,223 total
includes taxes & fees
15 May - 16 May
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Dining

Relaxing Two Bedroom Cabin - 10 minutes to Camden!

Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Lincolnville
8.0 out of 10, Very good, (5 reviews)
"We booked this place for Memorial Weekend, and drove into Camden to explore the town. Host was so friendly and responsive, the cabin was so clean and quaint/cute, loved the location that we go that cabin feel but could drive a short distance to get into town/harbor, and overall had a great time! "
United States
Kimberly
The price is HK$1,376
HK$3,138 total
includes taxes & fees
15 May - 16 May
Relaxing Two Bedroom Cabin - 10 minutes to Camden!
Fridge, microwave, oven, stovetop

Tides' Reach - Private Waterfront King Beds

Tides' Reach - Private Waterfront King Beds
Orland
9.8 out of 10, Exceptional, (24 reviews)
"This place is an absolute treasure! Secluded but close to all the necessities need to make your vacation amazing!"
United States
Joshua G.
The price is HK$1,488
HK$4,072 total
includes taxes & fees
27 May - 28 May
Tides' Reach - Private Waterfront King Beds
Exterior

Blue Hill in the Woods

Blue Hill in the Woods
Blue Hill
8.0 out of 10, Very good, (1 review)
"Nice new apartment upstairs of the garage. It’s a spacious single room (except the bathroom of course), nicely laid out with pleasant lighting through windows looking out towards the trees. The “kitchen” is minimal: a dorm-sized fridge, microwave, toaster oven, water kettle and coffee maker. Sufficient for our needs but not enough for an extended stay. Given that the rental is a one-room studio with laminate flooring, the pet fee seemed a bit steep, but the apartment itself was a good bargain...
United States
Eric S.
The price is HK$1,078
HK$1,764 total
includes taxes & fees
15 May - 16 May
Blue Hill in the Woods
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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Top Islesboro Hotel Reviews

Colonial Gables Oceanfront Village

Colonial Gables Oceanfront Village

10/10 Excellent
"Pleasantly surprised at the accommodations and views of the bay from our cottage. The porch was great. Parking right at the cottage. Check in was easy and reception was very friendly and helpful. The cottage had a small but well equipped kitchen with everything we could need. The living room had a table and chairs, desk and plenty of furniture and a large TV. The bedroom had 2 queen beds that were comfortable but it was a bit cramped for 4 people with luggage but it worked. The shower was great and the bathroom was big. Lighting was great and the timed heater made it nice and warm for showering. The only complaint was that there was nowhere to put anything at the sink area as the sink looked pretty but no counter area at all so difficult to put anything down. We would definitely stay there again and recommend it to our friends. It was a short ride to the downtown area, stores, and restaurants."
Susan 2-night trip
Posted 5 hours ago
Colonial Gables Oceanfront Village

Find out more about Islesboro

Search for holiday rentals in Islesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Islesboro using one of the methods below:

  • View our selection of featured holiday rentals in Islesboro
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Look no further and take a look at our great range of rental properties in Islesboro!

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 8 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 Lincolnville Beach. Warren Island State Park 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.