Vacation rentals in Islesboro Island

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Top-rated vacation rentals in Islesboro Island

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Guest favorite

Cottage in Lincolnville

4.91 out of 5 average rating, 330 reviews

Eco-friendly studio - ocean views, close to beach

Ecofriendly guest cottage in the heart of Lincolnville Beach, on Rt 1 (a busy road that runs from Maine to Florida), is a sunny studio (with blinds) with a murphy bed, full bathroom, breakfast nook (sink/fridge/microwave - no oven, no stovetop) and amazing views of Penobscot Bay. It's a quick walk to one of Maine's sandy beaches, restaurants, shops, coffee roaster, and a neighborhood market. Drive a few miles to hiking trails, Mount Battie, and the towns of Belfast, Camden, Rockport + Rockland.

Jan 5 – 12

G$27,617 GYD per night

Guest favorite

Yurt in Appleton

4.96 out of 5 average rating, 227 reviews

SUMMER ROSE a Yurt for ALL Seasons

SUMMER ROSE - Overlooking the Field of Dreams pasture, and future pond, is a spacious wooden yurt with a spectacular ceiling, personal hot tub and "Hideout" a screened in sanctuary. The Appleton Retreat is situated on 120 acres of privately owned land. To the south, a short walk from Summer Rose, is the Pettengill Stream, a resource protected area where you can view wildlife or kayak; and to the north, a wooded trail leads to a secluded pond on 1,300 acres of Nature Conservancy protected land.

Dec 18 – 25

G$33,951 GYD per night

Guest favorite

Guesthouse in Lincolnville

4.97 out of 5 average rating, 327 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

Aug 14 – 21

G$32,900 GYD per night

Guest favorite

Guesthouse in Lincolnville

4.98 out of 5 average rating, 161 reviews

Peaceful Suite - Hiking, Beach, Nature

Welcome to the “East Wing”! The complete apartment is new: salt box style with beautiful views of nature (hummingbirds, fireflies, starry skies). The East Wing is first to greet the sun in the morning. Enjoy your coffee on the private deck, or sip wine at night by the fire pit. Close to Tanglewood Rd (4H camp) , Camden Hills State Park trails, and Lincolnville Beach(1 -2 miles). The area is quiet- yet just a few miles away from shopping and restaurants in Camden, Belfast, & Rockland.

Nov 14 – 21

G$33,077 GYD per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Jan 6 – 13

G$20,475 GYD per night

Guest favorite

Apartment in Belfast

4.99 out of 5 average rating, 262 reviews

Room with a Brew

Welcome to our new building. "A Room With a Brew" is located above Belfast's newest craft brewery, Frosty Bottom Brewing. A small community supported brewery open 2 days/week for 3-4 hours for beer share members. Guests can request a tour of the brewery and sample some fresh beer. Owners live in downtown Belfast and are available should any issues arise during your stay. The apartment/brewery is located 3 miles from downtown on a quiet road that offers local hiking and biking.

Jan 7 – 14

G$27,202 GYD per night

Guest favorite

Guesthouse in Sedgwick

4.96 out of 5 average rating, 235 reviews

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Apr 15 – 22

G$29,075 GYD per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 14 – 21

G$17,120 GYD per night

Guest favorite

Cottage in Rockport

4.95 out of 5 average rating, 165 reviews

Designer’s Coastal Retreat with Simple Luxuries

A designer’s stunning retreat just a short walk to Rockport harbor. This newly renovated 1920’s one bedroom cottage is tucked into a forested granite hillside with oversized windows to take in the view. Artfully furnished with a minimalist sensibility, the space has been fully winterized in order to be a year round sanctuary. A top of the line steam shower, heated bathroom floor, modern gas fire place, and pigmented plaster walls add touches of luxury.

Dec 17 – 24

G$30,230 GYD per night

Guest favorite

Tiny home in Trenton

5.0 out of 5 average rating, 135 reviews

The Tiny House with the Enormous View of Acadia

The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Dec 6 – 13

G$30,503 GYD per night

Guest favorite

Guest suite in Rockland

4.98 out of 5 average rating, 347 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes gets you to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOGS

Oct 7 – 14

G$20,489 GYD per night

Guest favorite

Cabin in Deer Isle

4.89 out of 5 average rating, 129 reviews

Long Cove Artist Cottage

Rustic little self-contained Maine cottage on mahogany deck with outdoor shower overlooking flower gardens and Long Cove. Sweet and simple. Two rooms plus galley kitchen with eating area. Walking, swimming, and boating: everything you need in one location, the perfect retreat. Your artist hosts are available in adjacent house.

May 12 – 19

G$23,257 GYD per night