The Anchorage, an oceanfront home with two private beaches on Islesboro Island

Top rated by guests
The Anchorage
kitchen
kitchen
breakfast table
sparkling water, master bedroom window
review stars
10Outstanding
(10 Ratings)
"wonderful location and great owner"
marc d.
Don't miss out! Price and availability may change
10 / 10
Outstanding(10 Ratings)

House in Islesboro, ME

9 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

The Anchorage is a spectacular oceanfront peninsula property on Islesboro's eastern rocky coast overlooking Penobscot Bay. Enjoy sunrises, sunsets, moonrises and sunny afternoons, relaxing on the new covered deck or in the hammock with a book. With two private beaches, gorgeous ocean views from the living room, dining room, and three of the four bedrooms, the property is an ideal vacation space. There are sweeping lawns for relaxing or playing games, charming gardens, a private dock, and beaches for swimming in the cove.

The home, at the end of a quiet road, is in walking distance to tennis courts and playground, and close to the island's two markets, community center, farmer's market, post office, historical society, light house, town library, health center, and ice cream shop. Fully equipped kitchen, gas grill, new paint and furnishings throughout.

Enjoy morning coffee overlooking the bay while you watch eagles and osprey soar by along with loons, cormorants, and of course seagulls. You might well spot a family of porpoise, or a seal bobbing up to say hello. Schooners and other boats dot the bay along with the occasional working lobster boat. Boats are important in Islesboro; indeed, a boat is the only way to reach the island. Our car and passenger ferry departs from Lincolnville Beach frequently. On the twenty minute ferry ride, you'll experience the lovely sense of leaving the world behind. Whether you are looking for a tranquil getaway or an ideal setting for family fun and memories, The Anchorage is a magical place.

Amenities at The Anchorage, an oceanfront home with two private beaches on Islesboro Island

Non-smoking
No pets allowed
Family friendly

Map of Islesboro, ME


Ratings and reviews

10 / 10
Outstanding(10 Ratings)
10 / 10Outstanding·Jun 2026
wonderful location and great owner
10 / 10Outstanding·May 2026
If you’re looking for a private quintessential costal Maine retreat this is it. The property which sits at the very end of Hewes Point Rd gives 180 degree views of Penobscot Bay from the northwest to the southeast. There are two beautiful beaches on each side of the large well manicured yard which extends to a narrow point about 100 yards to the north of the dwelling. The pebble beach on the west side looks like it is shared but the one just off the house’s beautiful deck is completely private. Both are useable even at high tide and they become expansive at low tide. Access to the shore in just about any place in northern Maine typically requires a climb down and this property is not an exception, The beach on the west side of the yard has a set of stairs but the bigger and more private one in the east has a rock retaining wall that has stair like qualities but small children and unsteady elderly folks will surely need a helping hand. The house has been kept up very nicely and has a solid rustic feel and the large picture windows in the spacious family and dining rooms provide stunning views of the ocean. The plumbing, hot water supply and pressure were first rate. The tap water was clear, cold, colorless and tasteless so there is no need to bring bottled water. We had no difficulties preparing meals that ranged from a multicourse Sunday dinner to hamburgers on the outdoor grill for the six adults and one toddler. All in all, a gorgeous spot and highly recommended.
10 / 10Outstanding·Oct 2025
Beautiful home on the edge of Maine. Easy ferry ride to this island paradise. Todd and Kristen have the house well appointed and are easily available for questions. We really enjoyed our peaceful stay.
10 / 10Outstanding·Aug 2025
Beautiful property. The crew from Northern Maine saw seals, sailboats, sea glass and even a full rainbow over the ocean. Best work accommodations ever!

$$$$
vrbo logo

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at The Anchorage, an oceanfront home with two private beaches on Islesboro Island. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is The Anchorage, an oceanfront home with two private beaches on Islesboro Island pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at The Anchorage, an oceanfront home with two private beaches on Islesboro Island?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.