Bailey Island Rentals
From $444 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 $444 per night (USD)VRBO
From $839 per night (USD)Expedia
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 $839 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 ...
Click For PricingVRBO
From $262 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 $262 per night (USD)Expedia
From $772 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 $772 per night (USD)VRBO
From $354 per night (USD)Expedia
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 $354 per night (USD)Expedia
From $255 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 $255 per night (USD)VRBO
From $425 per night (USD)Expedia
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 $425 per night (USD)Expedia
From $465 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 $465 per night (USD)VRBO
From $561 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 $561 per night (USD)Expedia
From $490 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 $490 per night (USD)VRBO
From $282 per night (USD)Expedia
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 $282 per night (USD)Expedia
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 $325 per night (USD)Expedia
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 $325 per night (USD)Expedia
From $314 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 $314 per night (USD)VRBO
From $243 per night (USD)Expedia
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 $243 per night (USD)Expedia
From $205 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 $205 per night (USD)VRBO
From $250 per night (USD)Expedia
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 $250 per night (USD)Expedia
From $157 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 $157 per night (USD)VRBO
From $1199 per night (USD)Expedia
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 $1199 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 $233 per night (USD)Expedia
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 $233 per night (USD)Expedia
From $182 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 $182 per night (USD)VRBO
From $291 per night (USD)Expedia
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)Expedia
From $198 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 $198 per night (USD)VRBO
From $354 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 $354 per night (USD)Expedia
From $534 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 $534 per night (USD)VRBO
From $186 per night (USD)Expedia
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)Expedia
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 $390 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 $390 per night (USD)Expedia
From $275 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 $275 per night (USD)VRBO
From $214 per night (USD)Expedia
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 $214 per night (USD)Expedia
From $395 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 $395 per night (USD)VRBO
From $355 per night (USD)Expedia
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 $355 per night (USD)Expedia
From $222 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 $222 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 $229 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 $229 per night (USD)VRBO
From $245 per night (USD)Expedia
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 $245 per night (USD)Expedia
From $377 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 $377 per night (USD)VRBO
From $231 per night (USD)Expedia
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)Expedia
From $248 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 $248 per night (USD)VRBO
From $406 per night (USD)Expedia
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 $406 per night (USD)Expedia
From $310 per night (USD)VRBO
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 $310 per night (USD)VRBO
From $208 per night (USD)Expedia
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, ...
From $208 per night (USD)Expedia
From $435 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 $435 per night (USD)VRBO
From $249 per night (USD)Expedia
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 $249 per night (USD)Expedia
From $350 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 $350 per night (USD)VRBO
From $1440 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 $1440 per night (USD)Expedia
From $379 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 $379 per night (USD)VRBO
From $381 per night (USD)Expedia
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 $381 per night (USD)Expedia
From $1066 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 $1066 per night (USD)VRBO
From $327 per night (USD)Expedia
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 $327 per night (USD)Expedia
From $783 per night (USD)VRBO
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 $783 per night (USD)VRBO
From $658 per night (USD)Expedia
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 $658 per night (USD)Expedia
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 $366 per night (USD)Expedia
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 $366 per night (USD)Expedia
From $488 per night (USD)VRBO
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 $488 per night (USD)VRBO
From $637 per night (USD)Expedia
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 $637 per night (USD)Expedia
From $328 per night (USD)VRBO
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 $328 per night (USD)VRBO
From $438 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 $438 per night (USD)Expedia
From $304 per night (USD)VRBO
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled right on the water’s edge, this charming one-bedroom cottage is the perfect retreat for someone seeking peaceful ...
From $304 per night (USD)VRBO
From $372 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 $372 per night (USD)Expedia
From $797 per night (USD)VRBO
The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**Please read important notice for 2025 rental season below.** Perched on the water's edge, The Overlook offers command ...
From $797 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
Click For PricingVRBO
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 PricingVRBO
From $446 per night (USD)Expedia
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 $446 per night (USD)Expedia
From $338 per night (USD)VRBO
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 $338 per night (USD)VRBO
From $406 per night (USD)Expedia
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 $406 per night (USD)Expedia
From $200 per night (USD)VRBO
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)VRBO
From $320 per night (USD)Expedia
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 ...
From $320 per night (USD)Expedia
From $428 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 $428 per night (USD)VRBO
From $438 per night (USD)Expedia
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 $438 per night (USD)Expedia
From $473 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 $473 per night (USD)VRBO
From $491 per night (USD)Expedia
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 $491 per night (USD)Expedia
From $298 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 $298 per night (USD)VRBO
From $458 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 $458 per night (USD)Expedia
From $367 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 $367 per night (USD)VRBO
From $321 per night (USD)Expedia
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)Expedia
From $364 per night (USD)VRBO
Situated at the waters edge with picturesque sunset views to Mt Washington.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Whitesail's House! This lovely seaside cape is located near the end of Bailey Island, on the western shore. ...
From $364 per night (USD)VRBO
From $279 per night (USD)Expedia
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 $279 per night (USD)Expedia
From $430 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 $430 per night (USD)VRBO
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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 ...
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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 $264 per night (USD)Expedia
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 $264 per night (USD)Expedia
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
From $491 per night (USD)Expedia
This beautiful 3 bedroom, 2 bath house is located right towards the end of Orr's Island.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Crosswinds! This beautiful 3 bedroom, 2 bath house is located right towards the end of Orr's Island, Maine. ...
From $491 per night (USD)Expedia
From $334 per night (USD)VRBO
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
New Listing for 2025 ! Be the first to enjoy the serenity of this lovely home! **Charming Coastal Retreat on the coas ...
From $334 per night (USD)VRBO
From $736 per night (USD)Expedia
A multi-level home on the cliffs of Casco Bay!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Cliffside! This 3 bedroom, 2 bath stunner sits right on the cliffs of the open Atlantic Ocean. Cliffside is ...
From $736 per night (USD)Expedia
From $419 per night (USD)VRBO
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
Welcome to Sea Mist Overlook – a peaceful Harpswell cottage with stunning ocean views and classic coastal charm! Locate ...
From $419 per night (USD)VRBO
From $605 per night (USD)Expedia
Oceanfront Escape: Deck & Granite Steps to Shore
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
Spectacular Oceanfront Getaway on the Shores of Harpswell Water's Edge Shore Cottage – Wake up to breathtaking ocean v ...
From $605 per night (USD)Expedia