Holiday rentals in Islesboro

Cute Midcoast Cottage w Hot Tub

Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

Location · Family · Air conditioning

Milk House

nice little cottage in Dark Harbor, near to everything. queen bed, so sleeps up to two in a quiet location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speed excellent, though I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, we are on an island, which must be accessed by boat or ferry, so service can be interrupted. there's a gym at the Community Center, $10/day pass.

Location · Family · Kitchen

Birch Cottage · Just You & Quantabacook Lake

Kick back and relax in this serene, stylish, and newly renovated space. Birch Cottage is the perfect rustic waterfront getaway--a retreat for couples and solitude seekers. Unwind and escape to this enchanting, woodsy, lakefront property on gorgeous Quantabacook Lake. Cottage is ideal for both romantic couple retreats and peaceful solo excursions. Nestled among tall pines and just feet from shore, this magical haven offers breathtaking views and a tranquil atmosphere for your holiday getaway.

Value · Location · Comfort

Sunlit Cottage on Crockett Cove

Heron Cottage on Crockett Cove Cove Meadow, Stonington Maine Rare summer opening: August 3 - 6 (3 nights) * 1 Queen Bedroom/ 1 Full Bath with high quality linens * 2.5 Acres on Crockett Cove's Tidal Estuary * Tandem kayak included! * Firepit, hammock and seating area by the water * 8 minutes to Mailboat Ferry to Isle au Haut (Acadia) * 5 minutes to Aragosta & Barred Island Preserve * Follow us: @covemeadowcottage Also available during the Winter & Spring- please see my separate listing

Location · TV · Access

Queen bed cabin, The Anchorage 4

Cabin 4 is perfect for a couple with a queen size bed, Keurig and complimentary coffee pods. While she doesn't have a porch, guests are welcome to enjoy the common area by the creek. When permits allow, we will try and setup a fire. Are you looking for a different size cabin or your preferred dates aren't available? Visit our host profile to see all of our cottages at The Anchorage. Just click on our profile picture twice (x2) and scroll to the bottom to see our other 10 cabin options.

Location · Hospitality · Beach

"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 from 8 am to 4 pm everyday! We are closed for Winter, will re-open Mid-April. Thank you.

Value · Family · Amenities

Sunny 2 Bedroom cottage - Walk to the beach!

Single story cottage in the heart of Midcoast Maine! This 2 bedroom cottage is in the Lincolnville Beach area. Located within eyesight and walking distance of the public beach, the Islesboro Ferry terminal, McLaughlin’s restaurant, and the Beach Store. Property is located on US route 1- just 6 miles north of Camden (8 minute drive), and less than 15 minutes south of Belfast. This year-round cottage provides a lovely retreat for resting while exploring all the Midcoast has to offer.

Value · Family · Indoor spaces

"Eagles Nest" Waterfront Cottage

Escape to our delightful waterfront cottage nestled along the rugged and breathtakingly beautiful coast of Maine. This charming and cozy retreat offers expansive water views and serene surroundings - ensuring the perfect blend of comfort and tranquility. Take in the fresh salty air, the soothing sounds of waves lapping the shore, and create lasting memories to cherish in this memorable seaside sanctuary. Book your stay with us and experience the enchanting beauty of Penobscot Bay.

Location · Kitchen · Layout

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and character of the home while integrating sophisticated elements throughout. Prime location within walking distance to local coffee shop, ice cream parlor and charming gift shop. All points of island are within a 10 minute drive of the home. Massive, private bedrooms perfect for multiple couples or families. Reach out with any questions or concerns you may have!

Family · Location · Bathroom

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Location · Family · Outdoor spaces

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Family · Value · Cleanliness

Tiny Treehouse Cabin 100 Acres Kayaks

Snuggle up with your favorite person or pet in this tiny treehouse cabin in the woods. A comfortable queen bed, mini woodstove, and tiny kitchenette are all inside! Get cozy in the Maine woods, but stay close enough for cell service and a quick trip to the store. Outside the treehouse there are 100 acres of trails for you to hike, ski or snowshoe. In the warmer months, use the canoe or kayaks for a paddle or fishing!

Location · Heating · Accuracy