Bailey Island Rentals
From $392 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 $392 per night (USD)VRBO
From $926 per night (USD)Expedia
Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Available for weekly rentals during the summer season and two night and more stays in the off seasons.The house is also ...
From $926 per night (USD)Expedia
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ON the Water in Harpswell Maine
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Little Island Cottages are the quintessential Maine coast experience. #45 is one of three cottages built on a wharf. Thi ...
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From $329 per night (USD)Expedia
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 ...
From $329 per night (USD)Expedia
From $806 per night (USD)VRBO
The Captain York House
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
The Historic Captain York House in a unique New England home that was originally one home built along side another. Thi ...
From $806 per night (USD)VRBO
From $539 per night (USD)VRBO
Oceanfront cottage with stunning sunrises over the Cribstone Bridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Seaside Sunrise! Seaside Sunrise is a newly renovated waterfront cottage that is calling your name. Sit comf ...
From $539 per night (USD)VRBO
From $329 per night (USD)VRBO
Waterfront cottage situated at the mouth of Mackerel Cove. Amazing sunset views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sea Scent! Take in Maine's coast in this tastefully decorated updated cottage right on the water's edge of ...
From $329 per night (USD)VRBO
From $220 per night (USD)VRBO
Spend a relaxing time on Orr's Island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 4
The Bea House is a spacious 4 bedroom Dutch Colonial style home located on Harpswell Sound at the southerly end of Orr's ...
From $220 per night (USD)VRBO
From $321 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 $321 per night (USD)VRBO
From $455 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! This wonderful Turn-of-the-Century New England-style cottage sits on the water's edge at the mout ...
From $455 per night (USD)VRBO
From $610 per night (USD)VRBO
Mackerel Cove, Bailey Island. Fully Equipped Luxury Home. Sleeps v Comfortable 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Completed in 2019, 3 bedroom, 3 full ensuite bathroom cottage located directly across from Mackerel Cove (voted one of M ...
From $610 per night (USD)VRBO
From $576 per night (USD)Expedia
Enjoy the Fall Colors on the Coast of Maine!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The moment you arrive to this warm and inviting cottage, you will feel worlds away from the hectic everyday life. This c ...
From $576 per night (USD)Expedia
From $545 per night (USD)VRBO
Stover's Cove Beach Coastal Retreat
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Loaded with amenities: plenty of room to sleep. The main house has 5 comfortable bedrooms and 2 full baths; there is a s ...
From $545 per night (USD)VRBO
From $563 per night (USD)VRBO
Beautiful coastal Maine home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Our home was built in 2001 with a stunning open-concept first floor that features beautiful hardwood floors. Natural lig ...
From $563 per night (USD)VRBO
From $275 per night (USD)VRBO
Quintessential Maine cottage overlooking the Cribstone Bridge with nearby beach access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Wentworth Cottage! When crossing over the world famous Cribstone Bridge onto Bailey Island, look to your rig ...
From $275 per night (USD)VRBO
From $534 per night (USD)VRBO
Oceanside cottage perched near the Giant Stairs, offering amazing panoramic open ocean views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Surfside! This three-bedroom, two full bath cottage is the perfect getaway spot for you. On the main floor, ...
From $534 per night (USD)VRBO
From $319 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! Walk into a little piece of heaven when at the Nautical Nest! The quintessential charm and d ...
From $319 per night (USD)VRBO
From $316 per night (USD)VRBO
Enjoy spectacular sunset and water views from the deck and balconies with water access.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to West Shore House! This well-equipped rental is perched up on the edge of a hill on the quiet West Shore Road ...
From $316 per night (USD)VRBO
From $257 per night (USD)VRBO
Classic Maine Cottage with astonishing views located within walking distance to Cedar Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Bring the kids with you to this family-friendly cottage located on beautiful Bailey Island. Enjoy easterly views while y ...
From $257 per night (USD)VRBO
From $171 per night (USD)VRBO
! Enjoy beautiful Orr's Island. .
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The Rose House is a quaint New England Cape located on the southerly end of Orr's Island in the Town of Harpswell, Maine ...
From $171 per night (USD)VRBO
From $234 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 $234 per night (USD)VRBO
From $174 per night (USD)VRBO
Charming 1 Bedroom Coastal Cottage. Steps Away From Stovers Point Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come and enjoy your stay at our charming cottage on Stovers Point in Harpswell. You will experience a true Maine vacatio ...
From $174 per night (USD)VRBO
From $790 per night (USD)VRBO
Nicest Waterfront in Maine w\/ Private Beach!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful, classic, recently built luxury home located at the center of Mackerel Cove, known as the most photographed wa ...
From $790 per night (USD)VRBO
From $383 per night (USD)Expedia
The Anchorage - Charming Bailey Isl cottage with beautiful views of Casco Bay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 3BR, 1BA Bailey Island cottage is perfectly set in the Oceanside neighborhood with beautiful easterly view ...
From $383 per night (USD)Expedia
From $1222 per night (USD)VRBO
NEW -Beautiful Renovated Private Ocean Front Cottage with Sunsets and Sunrises
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 6
NEW to the rental market!! This beautifully renovated, PRIVATE waterfront seaside cottage is ready for your immediate we ...
From $1222 per night (USD)VRBO
From $203 per night (USD)VRBO
Family & Pet Friendly Log House On Casco Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful waterfront property on Orr's Island. Walking distance to famous Cribstone Bridge, Cook's Lobster House, The Sa ...
From $203 per night (USD)VRBO
From $291 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! This studio garage apartment is located right on Harpswell Sound. It offers beautiful s ...
From $291 per night (USD)VRBO
From $177 per night (USD)VRBO
Adorable cottage with million dollar view and short walk to stunning beach.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
If you grew up experiencing summers on the Maine coast, our cottage will bring you back in time. Our cottage offers a m ...
From $177 per night (USD)VRBO
From $273 per night (USD)VRBO
Sweet Bailey Island Home with Beautiful Westerly Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy spectacular westerly views over Harpswell Sound and out to Casco Bay from this well-appointed two-bedroom year-rou ...
From $273 per night (USD)VRBO
From $341 per night (USD)Expedia
Great location on Bailey Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Completely renovated cottage within walking distance to beaches, restaurants and the most beautiful coastal vistas you c ...
From $341 per night (USD)Expedia
From $509 per night (USD)VRBO
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly Constructed Friendly Cottage on Oceanside, Bailey Island is now available for your seaside vacation, no matter the ...
From $509 per night (USD)VRBO
From $186 per night (USD)VRBO
Charming waterfront cottage with large yard
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 6
Spacious home with a fully furnished kitchen. We are located on a quiet peninsula on Harpswell Sound, with a beautiful ...
From $186 per night (USD)VRBO
From $125 per night (USD)VRBO
Secluded Casco Bay Waterfront Cabin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please note: our rental week is Saturday to Saturday. Enjoy the Maine coast in this cozy and private cabin, situated on ...
From $125 per night (USD)VRBO
From $335 per night (USD)VRBO
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 $335 per night (USD)VRBO
From $249 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! Looking for the perfect couples getaway? Well look no further! This quaint cottage, located i ...
From $249 per night (USD)VRBO
From $208 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! This cute little cottage is located almost at the end of Bailey Island. With a beautifu ...
From $208 per night (USD)VRBO
From $314 per night (USD)VRBO
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lowell’s Cove Getaway is a beautiful 2 story home which overlooks the sparkling waters of Lowell’s Cove on beautiful Orr ...
From $314 per night (USD)VRBO
From $354 per night (USD)VRBO
3 bedroom, 2 bathroom classic Maine cottage with ocean views into Mackerel Cove
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sherrill's Seaside Cottage! This classic Maine cottage is perched high on the island offering elevated views ...
From $354 per night (USD)VRBO
From $242 per night (USD)VRBO
Newly Renovated Cottage in the Village area of Orr`s Island near the Scenic Cribstone Bridge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Compass Rose! This newly renovated cottage is situated in the heart of the village area of Orr s Island. Walk ...
From $242 per night (USD)VRBO
From $330 per night (USD)Expedia
Enjoy beautiful easterly views of Casco Bay from this charming 1BR cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Perfectly set in Bailey Island's Oceanside neighborhood, this charming cottage offers beautiful easterly views of Casco ...
From $330 per night (USD)Expedia
From $238 per night (USD)VRBO
Historic cottage with right of way to Little Harbor!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Hay! Looking for a rustic Maine cottage? Well look no further! This three-bedroom cottage has all the charm ...
From $238 per night (USD)VRBO
From $236 per night (USD)VRBO
This sweet cottage offers a shared pebbly beachfront and gorgeous sunset views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A very new and charming cozy cottage. Centrally located on the island at the end of Steamboat Road. Shared pebbly beach ...
From $236 per night (USD)VRBO
From $373 per night (USD)VRBO
Enjoy picturesque inlet views of a working harbor and sunny days at your oceanfront cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Salt Spray! This cozy cottage sits on one of the highest points on Bailey Island with breathtaking views all ...
From $373 per night (USD)VRBO
From $231 per night (USD)VRBO
Couples Cottage at Mackerel Cove - Enjoy your views of Mt. Washington on the Rooftop Deck!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Sand Dollar! Need a couples getaway? Well look no further! This recently updated one-bedroom cottage holds g ...
From $231 per night (USD)VRBO
From $254 per night (USD)VRBO
Charming 4 bedroom Classic Maine Cottage located near the giant stairs.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Satterthwaite! This lovely New England-style cottage is situated on a dead-end road in a great Bailey Island ...
From $254 per night (USD)VRBO
From $393 per night (USD)VRBO
Perched on the shore of picturesque Mackerel Cove, enjoy phenomenal sunsets and panoramic views.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Steamboat Landing! This charming two-bedroom cottage sits directly on Mackerel Cove. Waking up here you can ...
From $393 per night (USD)VRBO
From $437 per night (USD)VRBO
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming ocean front cottage with wrap-around deck. Wake-up to sunrise and coffee on the deck while the seals, ducks, ea ...
From $437 per night (USD)VRBO
From $343 per night (USD)Expedia
The Beach House Bailey Island Maine
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Cottage style apartment located at the Beach. With two designated parking spots and a private entrance leading into a t ...
From $343 per night (USD)Expedia
From $214 per night (USD)VRBO
Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views! Max 2 people.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
YOUR SAFETY IS OUR PRIORITY. WE FOLLOW ALL US CDC GUIDELINES and APPROVED PRODUCTS TO ASSURE YOUR SAFETY. Dear Guests, I ...
From $214 per night (USD)VRBO
From $515 per night (USD)VRBO
This spacious home offers a FANTASTIC covered porch, perfect to spend your days gazing at the ocean!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sunset Shore House! The Sunset Shore House was just built on the hillside of West Shore Road overlooking Har ...
From $515 per night (USD)VRBO
From $418 per night (USD)VRBO
3 Bedroom Oceanview Cottage just steps to desirable Stovers Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome To Stover s Hideway! This three-bedroom, one-and-a-half bathroom cottage is conveniently located just a five-mi ...
From $418 per night (USD)VRBO
From $216 per night (USD)VRBO
Cozy 2 bedroom cottage with beautiful views of Mackerel Cove!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This sweet single story cottage sits on Tip-Top Hillside, with views into Mackerel Cove and beyond. Enjoy sitting on the ...
From $216 per night (USD)VRBO
From $326 per night (USD)VRBO
This spacious 2nd floor garage apartment offers phenomenal open ocean views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Edgecliff! This spacious and sunny second floor garage apartment is located at the edge of the crashing surf ...
From $326 per night (USD)VRBO
From $601 per night (USD)Expedia
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 $601 per night (USD)Expedia
From $362 per night (USD)VRBO
Recently updated cottage featuring beautiful easterly views of Casco Bay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to Cedar Ledge Cottage! This recently updated, bright cottage features beautiful easterly views of Casco Bay, op ...
From $362 per night (USD)VRBO
From $438 per night (USD)VRBO
Beautifully landscaped, Spacious home, conveniently located in Harpswell
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Charming , comfortable home, 3 bedroom, 2.5 bath, Fresh Maine seafood! Now accepting long term bookings for winter month ...
From $438 per night (USD)VRBO
From $1049 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 $1049 per night (USD)VRBO
From $315 per night (USD)VRBO
Sea Rose Cottage - Cozy, Comfortable, Ocean Views on Orr's Island, Harpswell, ME
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Experience coastal living in our sunny and cozy cottage on Orr's Island in Harpswell, Maine! Relax on the covered porch ...
From $315 per night (USD)VRBO
From $435 per night (USD)VRBO
1890 Summer Cottage on an Ocean Bluff
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
This Maine summer cottage on Bailey Island sits on a high bluff overlooking the ocean. First bought by great, great gran ...
From $435 per night (USD)VRBO
From $580 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 $580 per night (USD)Expedia
From $692 per night (USD)VRBO
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE RED HOUSE The 100 year old Red House at the head of Mackerel Cove was built when most of Bailey Island was wild and ...
From $692 per night (USD)VRBO
From $311 per night (USD)VRBO
Cozy oceanfront cottage on Orr's Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This one bedroom guest cottage is great for a couple looking for an island escape. The property is located on a quiet c ...
From $311 per night (USD)VRBO
From $355 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 $355 per night (USD)VRBO
From $459 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 $459 per night (USD)Expedia
From $512 per night (USD)VRBO
Homeport - Modern oceanfront cottage overlooking quintessential Mackerel Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Having undergone a foundation-up renovation completed in August 2011, Homeport offers a modern design, allowing you to e ...
From $512 per night (USD)VRBO
From $279 per night (USD)Expedia
The Little House - Gorgeous Views of Lowell's Cove and Casco Bay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
From bold open ocean views, rugged Maine coastline, and easy water access via a shared beach, to a fresh, new interior, ...
From $279 per night (USD)Expedia
From $345 per night (USD)VRBO
Little Harbor - Crashing surf, sunrise views from this perfect Maine getaway.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***WE ARE HAPPY TO REPORT LITTLE HARBOR'S POST-STORM REPAIR AND RENOVATION IS NOW COMPLETE AND THE COTTAGE IS AVAILABLE ...
From $345 per night (USD)VRBO
From $310 per night (USD)Expedia
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This quaint one-bedroom cottage perched on the water's edge is the perfect spot for a small family or a romantic getaway ...
From $310 per night (USD)Expedia
From $619 per night (USD)VRBO
Just steps away from Stover's Point Beach, great for swimming and kayaking.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Compass Rose presents a rare opportunity to vacation just steps away from Stover's Point Beach! You'll appreciate o ...
From $619 per night (USD)VRBO
From $395 per night (USD)Expedia
Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perched overlooking Merriconeag Sound rests this charming, beautifully furnished 2BR, 1BA Bailey Island cottage. Perfect ...
From $395 per night (USD)Expedia
From $874 per night (USD)VRBO
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 $874 per night (USD)VRBO
From $455 per night (USD)Expedia
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perched overlooking Merriconeag Sound rests this charming, beautifully furnished 2BR, 1BA Bailey Island cottage. Perfect ...
From $455 per night (USD)Expedia
From $316 per night (USD)VRBO
Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This charming 2BR, 1BA quintessential Maine cottage is perfectly located on a quiet road, close to all Bailey Island has ...
From $316 per night (USD)VRBO
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Oceanfront Condo on Bailey Island with Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to a newly renovated 4 bed condo on the water in a complex called Cribstone Commons. Located directly after the ...
Click For PricingExpedia
From $554 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 $554 per night (USD)VRBO
From $280 per night (USD)Expedia
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect seaside retreat, The Bailey Island Condo is conveniently located on Bailey Island overlooking scenic Mackere ...
From $280 per night (USD)Expedia
From $398 per night (USD)VRBO
Panoramic ocean views from sunrise to sunset!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to A Point Of View! This renovated early 1800's cape is perched high up on Bailey Island offering open ocean vi ...
From $398 per night (USD)VRBO
From $200 per night (USD)Expedia
Cozy Cottage with stunning views of Stover's Cove.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Cozy 1 Bedroom 800sq ft Cottage overlooking Stover's Cove with a nice stone Patio in the front, along with a large fron ...
From $200 per night (USD)Expedia
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New! Cedar Rose Cottage with ocean views, vintage charm, and a modern touch.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to Cedar Rose Cottage. This is a home away from home you will never forget. Beautiful ocean views from almost ev ...
Click For PricingVRBO
From $459 per night (USD)VRBO
A newly renovated New Englander style home on the southern tip of Orr's Island.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Orr's Overlook! This classic New Englander is located at the southern tip of Orr's Island-a rustic yet renov ...
From $459 per night (USD)VRBO
From $356 per night (USD)VRBO
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' ...
From $356 per night (USD)VRBO
From $478 per night (USD)VRBO
A perfectly placed cottage overlooking Mackerel Cove!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Elroy Johnson Cottage! This perfectly placed cottage sits right on top of Bailey Island s Mackerel Cove! Wit ...
From $478 per night (USD)VRBO
From $502 per night (USD)VRBO
Whispering Winds Cottage, Offering Ocean views & Resort Amenities, 5 BR \/ 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 8
Brand new listing for 2024, hence why we do not have any reviews yet! Your Harpswell adventure begins at this charming, ...
From $502 per night (USD)VRBO
From $357 per night (USD)VRBO
Classic 3 bedroom cape on the stunning coast of Maine, sleeps 8 people
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for a special vacation in beautiful coastal Maine ? Visit the Hideaway in Harpswell. Located just 50 minutes fro ...
From $357 per night (USD)VRBO
From $321 per night (USD)VRBO
Ocean View, a 2 BR cottage on Bailey Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern, sunny cottage with sparkling open ocean views and lovely sunrises. Enjoy coffee and beverages on the deck while ...
From $321 per night (USD)VRBO
From $311 per night (USD)VRBO
Recently renovated 3 bedroom, 2 bathroom home with elevated views into Lowell`s Cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Watson's Landing! This sweet cottage is perched on the hill overlooking Lowell's Cove. It offers 3 bedrooms, ...
From $311 per night (USD)VRBO
From $298 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! This 3-bedroom, 2-bathroom home is tucked over a hill along the rocky western shore. Enjoy ...
From $298 per night (USD)VRBO
From $168 per night (USD)Expedia
Gorgeous 2 Bedroom, 2 Bathroom Waterfront Apartment with Access to Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gorgeous 2BR, 2BA, + Den waterfront apartment with balcony. Swim or kayak off of the building's dock. The space is near ...
From $168 per night (USD)Expedia
From $326 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 $326 per night (USD)VRBO
From $253 per night (USD)VRBO
Ocean's Edge sits right on Stover's Cove.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Ocean's Edge! This 2 bedroom, 1 bath cottage is perched perfectly inside the Stover's Cove area of Casco Bay ...
From $253 per night (USD)VRBO
From $414 per night (USD)VRBO
Near Stover's Cove with gorgeous views of the world famous Cribstone Bridge.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Bridgeview! This cute 3 bedroom, 2 full bath cottage sits comfortably near Stover's Cove with gorgeous views ...
From $414 per night (USD)VRBO