Bailey Island Rentals
From $496 per night (USD)VRBO
Wake to Sunrise on the Ocean
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy all three seasons, Spring Summer and the quiet of Fall. Central heat and fireplace will keep you toasty in this tr ...
From $496 per night (USD)VRBO
From $1036 per night (USD)Expedia
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
The well-appointed Captain Lawrence E. Johnson House is available for weekly rentals during the summer season and two-ni ...
From $1036 per night (USD)Expedia
Click For PricingVRBO
Enjoy breathtaking sunsets from this newly renovated studio on Bailey Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perched overlooking Merriconeag Sound, this newly renovated studio apartment offers an elevated deck to watch the breath ...
Click For PricingVRBO
From $804 per night (USD)VRBO
The Captain York House
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 12
The Historic Captain York House in a unique New England home that was originally one home built along side another. Thi ...
From $804 per night (USD)VRBO
From $459 per night (USD)VRBO
Johnson Homestead. One level living, ocean view with semi-private beach access.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Johnson Homestead is located on the south end of Bailey Island looking out at the entrance to Mackerel Cove. With on ...
From $459 per night (USD)VRBO
From $367 per night (USD)VRBO
Turn-of-the-Century Classic Maine Cottage with Sweeping Southeasterly Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Spindrift! Experience the quintessential Maine coastal getaway at Spindrift, a turn-of-the-century New Engla ...
From $367 per night (USD)VRBO
From $706 per night (USD)VRBO
Nautical themed Oceanfront Cottage located at the Mouth of picturesque Mackerel Cove!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Nautical Nest! One of three charming sister cottages on Bailey Island, each offering unforgettable sunsets a ...
From $706 per night (USD)VRBO
From $349 per night (USD)VRBO
Enjoy spectacular sunset and water views from the deck and balconies with water access.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to West Shore House! Perched high on a scenic hillside overlooking the sparkling waters of Casco Bay, West Shor ...
From $349 per night (USD)VRBO
From $259 per night (USD)VRBO
Classic Maine Cottage with astonishing views located within walking distance to Cedar Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Blue Heron! Breathe in the fresh Atlantic air and start your day with easterly sunrise views from the spaciou ...
From $259 per night (USD)VRBO
From $308 per night (USD)VRBO
The Nugget- Perfect 1 bedroom cottage. Across from Mackerel Cove, Johnson Field.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Nugget is a fully renovated 1 bedroom cottage with bathroom, kitchen and washer/dryer. Perfect for 2 people. Views o ...
From $308 per night (USD)VRBO
From $262 per night (USD)VRBO
Juniper Cottage on Bailey Island – A Peaceful, Relaxing, CLEAN Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Juniper Cottage on Bailey Island is ready to be your oasis in the coming summer months. This charming shake shingle summ ...
From $262 per night (USD)VRBO
From $227 per night (USD)VRBO
Perfect spot for a couples get-away, ocean views from the balcony and sitting area
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Goldsmith Apartment! Escape to the serene beauty of coastal Maine at Goldsmith Apartment, a charming studio ...
From $227 per night (USD)VRBO
From $479 per night (USD)VRBO
Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Friendly Cottage on Oceanside, Bailey Island is now available for your seaside vacation, no matter the season. This well ...
From $479 per night (USD)VRBO
From $420 per night (USD)Expedia
Rudman's Retreat. Deep waterfront 2 Bedroom home with spectacular sunset views.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located near the south end of Bailey Island, this comfortable custom-built year-round home sits along the coast with a w ...
From $420 per night (USD)Expedia
From $253 per night (USD)VRBO
Sweet 1 bedroom cottage tucked along Harpswell Sound' shore, quiet location and wonderful views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Garrison Cove! If you're dreaming of a peaceful and romantic coastal escape, Garrison Cove is the perfect re ...
From $253 per night (USD)VRBO
From $241 per night (USD)VRBO
Lovely deck to watch the boats come and go, and incredible sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Whitesail's Cottage! Tucked near the very end of picturesque Bailey Island, Whitesail's Cottage is the perfe ...
From $241 per night (USD)VRBO
From $371 per night (USD)VRBO
3 bedroom, 2 bathroom classic Maine cottage with ocean views into Mackerel Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sherrill's Seaside Cottage! Perched gracefully on a high point of the island, Sherrill's Seaside Cottage off ...
From $371 per night (USD)VRBO
From $301 per night (USD)VRBO
Historic cottage with right of way to Little Harbor!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Hay! Step back in time and enjoy the charm of coastal Maine at Hay, a rustic yet comfortable three-bedroom co ...
From $301 per night (USD)VRBO
From $264 per night (USD)VRBO
This sweet cottage offers a shared pebbly beachfront and gorgeous sunset views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Parciak Cottage! Nestled at the end of Steamboat Road and resting directly on the pebbly shoreline of Casco ...
From $264 per night (USD)VRBO
From $306 per night (USD)VRBO
Charming 4 bedroom Classic Maine Cottage located near the giant stairs.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Satterthwaite! Nestled in the middle of a peaceful dead-end road in a beloved Bailey Island neighborhood, Sa ...
From $306 per night (USD)VRBO
From $424 per night (USD)VRBO
This spacious home offers a FANTASTIC covered porch, perfect to spend your days gazing at the ocean!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sunset Shore House! Perched on the hillside of West Shore Road with sweeping views of Harpswell Sound, Sunse ...
From $424 per night (USD)VRBO
From $409 per night (USD)VRBO
Cozy 2 bedroom cottage with beautiful views of Mackerel Cove!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to The Studio! Perched on Tip-Top Hillside, this charming single-story cottage offers picturesque views of Mack ...
From $409 per night (USD)VRBO
From $340 per night (USD)VRBO
This spacious 2nd floor garage apartment offers phenomenal open ocean views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Edgecliff! Perched at the very edge of the crashing surf in beautiful Little Harbor, Edgecliff is a bright a ...
From $340 per night (USD)VRBO
From $1633 per night (USD)VRBO
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
JAQUISH LANE Perched on a stretch of rocky Maine coast, Jaquish Lane is a fully renovated oceanfront compound with stun ...
From $1633 per night (USD)VRBO
From $360 per night (USD)VRBO
Recently updated cottage featuring beautiful easterly views of Casco Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Cedar Ledge Cottage! This recently updated, bright cottage features beautiful easterly views of Casco Bay, op ...
From $360 per night (USD)VRBO
From $480 per night (USD)Expedia
Conveniently located, spacious home located on Bailey Island in Harpswell!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming , comfortable home, 2 full bedrooms plus 1 loft style bedroom, 2.5 bath, Very Close to Fresh Maine seafood! Now ...
From $480 per night (USD)Expedia
From $1103 per night (USD)VRBO
Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Experience charming, picturesque Bailey Island, a Maine Casco Bay Coastal Island destination for vacationers from all ov ...
From $1103 per night (USD)VRBO
From $711 per night (USD)Expedia
PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
HISTORIC ISLAND COTTAGE Built in 1918, The Gills is an original summer cottage perched above the sea at the very end of ...
From $711 per night (USD)Expedia
From $774 per night (USD)VRBO
THIS IS THE PLACE - Intimate cottage with oceanfront views and AC!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
THE RED HOUSE The 116 year old Red House at the head of Mackerel Cove was built when most of Bailey Island was wild and ...
From $774 per night (USD)VRBO
From $333 per night (USD)VRBO
Authentic maine cottage with direct water frontage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This turn of the century cottage has been lovingly preserved and updated tastefully by our family for 4 generations. Lo ...
From $333 per night (USD)VRBO
From $469 per night (USD)VRBO
Summer Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Peak Summer Weekly Rentals, Friday-Friday June 23 --> September 8 Shoulder Season Rentals June 2nd --> 19 September 6- ...
From $469 per night (USD)VRBO
From $626 per night (USD)Expedia
The Beach Rose - 3BR, 2BA home perched overlooking picturesque Mackerel Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Perched overlooking picturesque Mackerel Cove and The Back Beach, rests The Beach Rose, a beautiful coastal cottage with ...
From $626 per night (USD)Expedia
From $574 per night (USD)VRBO
Homeport - Modern oceanfront cottage overlooking quintessential Mackerel Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Completely renovated from the foundation up and completed in August 2011, Homeport boasts a modern design that allows yo ...
From $574 per night (USD)VRBO
From $465 per night (USD)Expedia
Little Harbor - Crashing surf, sunrise views from this perfect Maine getaway.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Little Harbor – A True Maine Escape Nestled on the pristine shores of Bailey Island, this cozy yet rustic oceanfront co ...
From $465 per night (USD)Expedia
From $436 per night (USD)VRBO
Sunset Cottage - Capture Breathtaking Sunsets from this Beautiful Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perched overlooking Merriconeag Sound rests this charming, beautifully furnished 2BR, 1.5 BA Bailey Island cottage. Perf ...
From $436 per night (USD)VRBO
From $1012 per night (USD)Expedia
The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perched on the water's edge, The Overlook offers commanding views of Merriconeag Sound to Casco Bay and its islands. You ...
From $1012 per night (USD)Expedia
From $604 per night (USD)VRBO
Sea Spray - Beautiful 2BR, 1BA cottage with expansive views of Casco Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Resting on the beautiful, rugged Bailey Island coastline is this well-appointed 2BR, 1 BA cottage offering stunning ocea ...
From $604 per night (USD)VRBO
From $394 per night (USD)Expedia
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The perfect seaside retreat, The Bailey Island Condo is conveniently located on Bailey Island overlooking scenic Mackere ...
From $394 per night (USD)Expedia
From $429 per night (USD)VRBO
Panoramic ocean views from sunrise to sunset!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to A Point of View! This beautifully renovated early-1800s Cape is perched high on Bailey Island with sweeping o ...
From $429 per night (USD)VRBO
Click For PricingExpedia
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Ole Greeley Cottage, a charming, classic Maine cottage with stunning ocean views over Merriconeag Sound. You' ...
Click For PricingExpedia
From $225 per night (USD)VRBO
Sunset Hideaway on Bailey Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Sunset Hideaway, a comfortable one bedroom apartment sleeping 4 guests. Perfectly located in the heart of Bai ...
From $225 per night (USD)VRBO
From $482 per night (USD)Expedia
Orchid Harbor, Bailey Island 3BR
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Orchid Harbor, a classic New England-style cottage home with stunning southerly views of Casco Bay. Perfectly ...
From $482 per night (USD)Expedia
From $389 per night (USD)VRBO
Great Location! Expansive deck with huge yard! Well maintained path to the rocky shoreline.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Giffin Log Cabin! Discover the charm, comfort, and serenity of coastal Maine at Giffin Log Cabin. A warm and ...
From $389 per night (USD)VRBO
From $372 per night (USD)VRBO
Cozy hotel suite in lovely Harpswell with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This memorable hotel suite is the perfect home base for your trip to Harpswell out on Bailey Island…..Nestled in a charm ...
From $372 per night (USD)VRBO
From $429 per night (USD)VRBO
Historic home located on Bailey Island within walking distance to the Giant's Stairs.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Coastal Breezes! If you're looking for the perfect Maine family getaway you've come to the right place ...
From $429 per night (USD)VRBO
From $802 per night (USD)VRBO
3 Bedroom Cottage with Easterly Ocean Views, and a path to the shore of Little Harbor.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Lee' Seascape! Perched dramatically above Little Harbor on a quiet dead-end road, Lee's Seascape is a classi ...
From $802 per night (USD)VRBO
From $1241 per night (USD)VRBO
Ocean front Home with Private dock - Winter rental Available
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Located in Harpswell, enjoy what this 5-bedroom house has to offer. With four king beds and one twin bed, guests find pl ...
From $1241 per night (USD)VRBO
From $488 per night (USD)VRBO
Wake to spectacular easterly ocean views and unforgettable Atlantic sunrises.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect coastal escape at Puffin's Perch on beautiful Bailey Island where classic Maine charm meets swee ...
From $488 per night (USD)VRBO
From $404 per night (USD)VRBO
In the heart of beautiful Bailey Island, this coastal retreat offers a blend of comfort and charm.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to beautiful Briar Rose! Perched in the heart of beautiful Bailey Island, this inviting coastal retreat offers t ...
From $404 per night (USD)VRBO
From $581 per night (USD)VRBO
Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Your Brand-New Coastal Maine Getaway! Be among the first to stay in this beautifully rebuilt coastal cottage ...
From $581 per night (USD)VRBO
From $359 per night (USD)VRBO
Newly renovated home with water views in the heart of Bailey Island
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Newly renovated 3 bedroom home on a hill with water views from both sides. Coffee with the sunrise, dinner with the suns ...
From $359 per night (USD)VRBO
From $299 per night (USD)VRBO
The Yellow Cottage is a 2-bedroom little getaway located right on its own private beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Yellow Cottage ! Your Private-Beach Escape on Casco Bay Perched in one of Bailey Island's most desirable ...
From $299 per night (USD)VRBO
From $301 per night (USD)VRBO
Serene cottage with a spectacular view on charming Bailey Island.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cross over the iconic Cribstone Bridge and escape to the beauty of Bailey Island in this charming one-bedroom cottage, p ...
From $301 per night (USD)VRBO
From $592 per night (USD)Expedia
Atlantic View - on the eastern cliffs of Bailey Island!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Entire Oceanfront Bailey Island Home: Views of Cliffs, Cove & Casco Bay Have the Entire Place to Yourself Escape to the ...
From $592 per night (USD)Expedia
From $489 per night (USD)VRBO
Gorgeous ocean views with private beach access.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Blue House! Tucked away on one of Bailey Island's premier locations overlooking Casco Bay, this gorgeous ...
From $489 per night (USD)VRBO
From $648 per night (USD)Expedia
Oceanside Oasis, New Listing, Steps from the Ocean, Perfect Bailey Isl Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Listing! Welcome to Oceanside Oasis — Your Coastal Escape on Beautiful Bailey Island Slow down to the rhythm of th ...
From $648 per night (USD)Expedia
From $257 per night (USD)VRBO
A rustic Maine log cabin with water access.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Log Cabin! Tucked beneath towering evergreens and surrounded by the quiet stillness of the Maine woods, ...
From $257 per night (USD)VRBO