7 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
The Historic Captain York House in a unique New England home that was originally one home built along side another. This allows for the house to split into a duplex. The historic Captain York House...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Bailey Island, Maine
Welcome to the Yellow Cottage !Your Private-Beach Escape on Casco BayPerched in one of Bailey Island's most desirable waterfront spots, the Yellow Cottage offers front-row views of sparkling Casco...
Created Jul 20, 2026
Apartment Vacation Rental In Harpswell, Maine
Welcome to Sunset Hideaway, a comfortable one bedroom apartment sleeping 4 guests. Perfectly located in the heart of Bailey Island within walking distance of local food options. The large lawn just...
Created Jul 20, 2026
3 Br Cottage Vacation Rental In Bailey Island, Maine
This turn of the century cottage has been lovingly preserved and updated tastefully by our family for 4 generations. Located on Merriconeag Sound, it has easy access from the back yard to the...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Bailey Island, Maine
Welcome to The Studio!Perched on Tip-Top Hillside, this charming single-story cottage offers picturesque views of Mackerel Cove and the surrounding coastline. Spend your mornings or evenings on the...
Created Jul 20, 2026
1 Br Cottage Vacation Rental In Bailey Island, Maine
Welcome to Parciak Cottage!Nestled at the end of Steamboat Road and resting directly on the pebbly shoreline of Casco Bay, Parciak Cottage offers a truly classic Maine coastal escape. Perfectly...
Created Jul 20, 2026
1 Br Apartment Vacation Rental In Bailey Island, Maine
Perched overlooking Merriconeag Sound, this newly renovated studio apartment offers an elevated deck to watch the breathtaking sunsets and a beautifully decorated interior with comfortable...
Created Jul 20, 2026
2 Br Apartment Vacation Rental In Harpswell, Maine
Cottage style apartment located at the Beach. With two designated parking spots and a private entrance leading into a two-bedroom one-bath space with a loft. Full kitchen living room area and...
Created Jul 20, 2026
4 Br Cottage Vacation Rental In Bailey Island, Maine
Enjoy all three seasons, Spring Summer and the quiet of Fall. Central heat and fireplace will keep you toasty in this traditional 1891shingle-style cottage sitting on a bluff with ocean views from...
Created Jul 20, 2026
1 Br Apartment Vacation Rental In Bailey Island, Maine
Welcome to Edgecliff!Perched at the very edge of the crashing surf in beautiful Little Harbor, Edgecliff is a bright and spacious second-floor garage apartment offering guests a true taste of...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
New Listing!Welcome to Oceanside Oasis Your Coastal Escape on Beautiful Bailey IslandSlow down to the rhythm of the tides at Oceanside, a serene island retreat where breathtaking water views, fresh...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
Welcome to West Shore House!Perched high on a scenic hillside overlooking the sparkling waters of Casco Bay, West Shore House offers some of the most captivating sunset views on Harpswell Sound....
Created Jul 20, 2026
3 Br Cottage Vacation Rental In Bailey Island, Maine
Welcome to Elroy Johnson Cottage!Perched directly above the sparkling waters of Bailey Island's Mackerel Cove, the Elroy Johnson Cottage offers an unparalleled coastal Maine experience. With...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
Welcome to the Blue House!Tucked away on one of Bailey Island's premier locations overlooking Casco Bay, this gorgeous 3-bedroom, 2-bath gem has everything you'll need for a dream vacation.Best of...
Created Jul 20, 2026
5 Br Cottage Vacation Rental In Bailey Island, Maine
JAQUISH LANEPerched on a stretch of rocky Maine coast, Jaquish Lane is a fully renovated oceanfront compound with stunning views of the sea from nearly every room. The property is well off the main...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
Welcome to A Point of View!This beautifully renovated early-1800s Cape is perched high on Bailey Island with sweeping open-ocean views of Casco Bay. From unforgettable Maine sunrises and sunsets to...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
Perched overlooking picturesque Mackerel Cove and The Back Beach, rests The Beach Rose, a beautiful coastal cottage with stunning westerly ocean views. You'll love spending your mornings on the...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
Completely renovated from the foundation up and completed in August 2011, Homeport boasts a modern design that allows you to take in stunning views of Mackerel Cove and its beach. Nestled among...
Created Jul 20, 2026
4 Br Cottage Vacation Rental In Bailey Island, Maine
Welcome to Satterthwaite!Nestled in the middle of a peaceful dead-end road in a beloved Bailey Island neighborhood, Satterthwaite is a classic New England-style cottage that captures the timeless...
Created Jul 20, 2026
3 Br Cottage Vacation Rental In Bailey Island, Maine
Welcome to Ole Greeley Cottage, a charming, classic Maine cottage with stunning ocean views over Merriconeag Sound. You'll love waking up to the sights and sounds of the ocean, exploring Harpswell...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Harpswell, Maine
Located near the south end of Bailey Island, this comfortable custom-built year-round home sits along the coast with a western view of Casco Bay and the mouth of Mackerel Cove. You can enjoy...
Created Jul 20, 2026
6 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
The well-appointed Captain Lawrence E. Johnson House is available for weekly rentals during the summer season and two-night-minimum stays in the off-season. The house is also available year-round...
Created Jul 20, 2026
4 Br Cottage Vacation Rental In Bailey Island, Maine
Welcome to Spindrift!Experience the quintessential Maine coastal getaway at Spindrift, a turn-of-the-century New England-style cottage perched right on the water's edge at the mouth of Little...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Harpswell, Maine
Welcome to Nautical Nest!One of three charming sister cottages on Bailey Island, each offering unforgettable sunsets and the true essence of Maine's coast.Step into your own little slice of...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Bailey Island, Maine
Welcome to Coastal Breezes!If you're looking for the perfect Maine family getaway you've come to the right place. This historic home is the second oldest home on Bailey Island. Though you would...
Created Jul 20, 2026
