Bailey Island Rentals
From $378 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 $378 per night (USD)VRBO
From $346 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 $346 per night (USD)VRBO
From $275 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 $275 per night (USD)VRBO
From $271 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 $271 per night (USD)VRBO
From $942 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 $942 per night (USD)VRBO
From $369 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 $369 per night (USD)Expedia
From $564 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 $564 per night (USD)VRBO
From $652 per night (USD)Expedia
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
- Bedrooms:
- 1
- 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 $652 per night (USD)Expedia
From $840 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 $840 per night (USD)VRBO
From $302 per night (USD)Expedia
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 $302 per night (USD)Expedia
From $334 per night (USD)VRBO
Beautifully landscaped, Spacious home, conveniently located 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! No ...
From $334 per night (USD)VRBO
From $354 per night (USD)Expedia
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 $354 per night (USD)Expedia
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 $454 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 $454 per night (USD)Expedia
From $482 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 $482 per night (USD)VRBO
From $353 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 $353 per night (USD)Expedia
From $421 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 $421 per night (USD)VRBO
From $359 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 $359 per night (USD)VRBO
From $458 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 $458 per night (USD)VRBO
From $720 per night (USD)VRBO
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 $720 per night (USD)VRBO
From $401 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. T ...
From $401 per night (USD)VRBO
From $516 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 $516 per night (USD)Expedia
From $372 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! This classic Maine cottage is perched high on the island offering elevated views ...
From $372 per night (USD)VRBO
From $242 per night (USD)VRBO
Historic cottage with right of way to Little Harbor!
- Bedrooms:
- 1
- 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 $242 per night (USD)VRBO
From $251 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 $251 per night (USD)VRBO
From $251 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 $251 per night (USD)VRBO
From $300 per night (USD)VRBO
Charming 4 bedroom Classic Maine Cottage located near the giant stairs.
- Bedrooms:
- 1
- 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 $300 per night (USD)VRBO
From $572 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! The Sunset Shore House was just built on the hillside of West Shore Road overlooking Har ...
From $572 per night (USD)VRBO
From $234 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 $234 per night (USD)VRBO
From $355 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 $355 per night (USD)VRBO
From $227 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! This well-equipped rental is perched up on the edge of a hill on the quiet West Shore Road ...
From $227 per night (USD)VRBO
From $270 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 $270 per night (USD)VRBO
From $210 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 $210 per night (USD)VRBO
From $432 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 $432 per night (USD)VRBO
From $409 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 $409 per night (USD)VRBO
From $332 per night (USD)Expedia
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Sea Mist Overlook – a peaceful Harpswell cottage with stunning ocean views and classic coastal charm! Locate ...
From $332 per night (USD)Expedia
From $372 per night (USD)VRBO
Oceanfront Escape: Deck & Granite Steps to Shore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spectacular Oceanfront Getaway on the Shores of Harpswell Water's Edge Shore Cottage – Wake up to breathtaking ocean v ...
From $372 per night (USD)VRBO
From $323 per night (USD)Expedia
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 $323 per night (USD)Expedia
From $1030 per night (USD)VRBO
Nicest Waterfront in Maine w/ Private Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful, classic, recently built luxury home located at the center of Mackerel Cove, known as the most photographed wa ...
From $1030 per night (USD)VRBO
From $206 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 $206 per night (USD)Expedia
From $267 per night (USD)VRBO
Newly Renovated Cottage in the Village area of Orr`s Island near the Scenic Cribstone Bridge
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Compass Rose! This newly renovated cottage is situated in the heart of the village area of Orr s Island. Walk ...
From $267 per night (USD)VRBO
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Sea Rose Cottage - Cozy, Comfortable, Ocean Views on Orr's Island, Harpswell, ME
- Bedrooms:
- 1
- 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 ...
Click For PricingExpedia
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 $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 $205 per night (USD)VRBO
! Enjoy beautiful Orr's Island. .
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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 $255 per night (USD)VRBO
Spend a relaxing time on Orr's Island
- Bedrooms:
- 1
- 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 $767 per night (USD)VRBO
Situated at the waters edge with picturesque sunset views to Mt Washington.
- Bedrooms:
- 3
- 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 $767 per night (USD)VRBO
From $296 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 $296 per night (USD)VRBO
From $377 per night (USD)VRBO
Charming 3BR, 2.5BA home with access to Merriconeag Sound
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sweet Retreat—a delightful 3-bedroom, 2.5-bathroom cottage nestled in a peaceful seaside neighborhood, offeri ...
From $377 per night (USD)VRBO
From $323 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 $323 per night (USD)VRBO
From $369 per night (USD)VRBO
Coastal Retreat Near Beach w/ Ocean Views !
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New for 2025! Come enjoy a peaceful fall or winter stay at this beautiful, dog-friendly home with lovely views — just a ...
From $369 per night (USD)VRBO
From $449 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 $449 per night (USD)VRBO
From $305 per night (USD)VRBO
Classic 3 bedroom cape on the stunning coast of Maine, sleeps 8 people
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Looking for a special vacation in beautiful coastal Maine ? Visit the Hideaway in Harpswell. Located just 50 minutes fro ...
From $305 per night (USD)VRBO
From $371 per night (USD)Expedia
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Nestled right on the water’s edge, this charming one-bedroom cottage is the perfect retreat for someone seeking peaceful ...
From $371 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 $333 per night (USD)Expedia
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
New Listing for 2025 ! Be the first to enjoy the serenity of this lovely home! **Charming Coastal Retreat on the coas ...
From $333 per night (USD)Expedia
From $476 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 $476 per night (USD)VRBO
From $450 per night (USD)VRBO
Whispering Winds Cottage, Offering Ocean views & Resort Amenities, 5 BR / 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 8
Welcome to Whispering Winds Cottage – A Timeless Retreat in Harpswell Your Harpswell adventure begins at Whispering Win ...
From $450 per night (USD)VRBO