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Bailey Island Vacation Rentals

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50 rentals in Bailey Island.
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Historic Captain York House: 7 Bed, 6.5 Bath, vacation rental in Bailey Island

Historic Captain York House: 7 Bed, 6.5 Bath

7 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Maine Oceanfront Home, vacation rental in Bailey Island

Maine Oceanfront Home

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay, vacation rental in Bailey Island

Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room, vacation rental in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Quaint Guest Cottage Overlooking Potts Harbor, vacation rental in Bailey Island

Quaint Guest Cottage Overlooking Potts Harbor

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views!, vacation rental in Bailey Island

Beaches, Boating, Cool Ocean Breezes, Trails & Incredible Views!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room, vacation rental in Bailey Island

THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quaint antique island home, vacation rental in Bailey Island

Quaint antique island home

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Fantastic Home, Waterview's Galore, vacation rental in Bailey Island

Fantastic Home, Waterview's Galore

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home, vacation rental in Bailey Island

PRIVATE OCEANFRONT RETREAT - enjoy the peace and quiet of an historic Maine home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brand new, year-round oceanfront home at the tip of Potts Pt. Private beach., vacation rental in Bailey Island

Brand new, year-round oceanfront home at the tip of Potts Pt. Private beach.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Breezes 2br Freeport, Maine Apartment, vacation rental in Bailey Island

Ocean Breezes 2br Freeport, Maine Apartment

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Shady Potts Point Cottage Cooled by Ocean Breezes, vacation rental in Bailey Island

Shady Potts Point Cottage Cooled by Ocean Breezes

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spectacular Oceanfront House on Maine Coast, vacation rental in Bailey Island

Spectacular Oceanfront House on Maine Coast

6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular Views, Peaceful & Private, vacation rental in Bailey Island

Spectacular Views, Peaceful & Private

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Summer cottage with all the comforts of home with a fabulous covered po, vacation rental in Bailey Island

Charming Summer cottage with all the comforts of home with a fabulous covered po

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family & Pet Friendly Log House On Casco Bay, vacation rental in Bailey Island

Family & Pet Friendly Log House On Casco Bay

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stover's Cove Beach Coastal Retreat, vacation rental in Bailey Island

Stover's Cove Beach Coastal Retreat

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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A cottage with a view and so much more!, vacation rental in Bailey Island

A cottage with a view and so much more!

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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HARPSWELL MAINE - The Cottage * AshPoint, vacation rental in Bailey Island

HARPSWELL MAINE - The Cottage * AshPoint

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Updated waterfront cottage w/private deck, gas grill & dock access, vacation rental in Bailey Island

Updated waterfront cottage w/private deck, gas grill & dock access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Phenomenal Home on Coast of Maine, vacation rental in Bailey Island

Phenomenal Home on Coast of Maine

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Camp Forever, vacation rental in Bailey Island

Camp Forever

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Great Internet Access! Quick stroll to beach, come relax & get away on Orr’s Is!, vacation rental in Bailey Island

Great Internet Access! Quick stroll to beach, come relax & get away on Orr’s Is!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vacation of a lifetime, Island in Maine, Ocean front property, golf, tennis,, vacation rental in Bailey Island

Vacation of a lifetime, Island in Maine, Ocean front property, golf, tennis,

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Front Cottage, Harpswell, ME, vacation rental in Bailey Island

Ocean Front Cottage, Harpswell, ME

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!, vacation rental in Bailey Island

Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Island Getaway the Nest, vacation rental in Bailey Island

Island Getaway the Nest

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Classic Maine Oceanfront Cottage, vacation rental in Bailey Island

Classic Maine Oceanfront Cottage

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Oceanfront Cottage with Spectacular Sunset Views, vacation rental in Bailey Island

Charming Oceanfront Cottage with Spectacular Sunset Views

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning views and comfort complete your ultimate Maine island vacation getaway., vacation rental in Bailey Island

Stunning views and comfort complete your ultimate Maine island vacation getaway.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Oceanfront cottage with stunning sunrises over the Cribstone Bridge, vacation rental in Bailey Island

Oceanfront cottage with stunning sunrises over the Cribstone Bridge

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New listing! Waterfront home w/ a furnished deck, ocean views, & a full kitchen, vacation rental in Bailey Island

New listing! Waterfront home w/ a furnished deck, ocean views, & a full kitchen

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Classic Maine Cottage with astonishing easterly views located walking distance t, vacation rental in Bailey Island

Classic Maine Cottage with astonishing easterly views located walking distance t

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Historic cottage with views of Mackerel Cove and right of way to Little Harbor!, vacation rental in Bailey Island

Historic cottage with views of Mackerel Cove and right of way to Little Harbor!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming cottage on Basin Cove just a short drive to the Dolphin Marina, vacation rental in Bailey Island

Charming cottage on Basin Cove just a short drive to the Dolphin Marina

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Waterfront Private Estate w dock on 6 acres, vacation rental in Bailey Island

Waterfront Private Estate w dock on 6 acres

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Classic Oceanfront Cottage on Orr's Island, vacation rental in Bailey Island

Classic Oceanfront Cottage on Orr's Island

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Centerview, deep water, tie up your boat to the dock, fish, swim or just relax, vacation rental in Bailey Island

Centerview, deep water, tie up your boat to the dock, fish, swim or just relax

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovingly restored 1905 cottage with phenomenal Easterly ocean views, just quick, vacation rental in Bailey Island

Lovingly restored 1905 cottage with phenomenal Easterly ocean views, just quick

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Point, Where the Land Meets the Sea, vacation rental in Bailey Island

The Point, Where the Land Meets the Sea

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Mackerel Cove, Bailey Island. Brand New Fully Equipped Luxury Home. Sleeps 8, vacation rental in Bailey Island

Mackerel Cove, Bailey Island. Brand New Fully Equipped Luxury Home. Sleeps 8

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely renovated cottage with fabulous views of Lowell`s Cove, just a short walk, vacation rental in Bailey Island

Lovely renovated cottage with fabulous views of Lowell`s Cove, just a short walk

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Rose Cottage - Cozy and Comfortable with Ocean Views on Orr's Island, vacation rental in Bailey Island

Sea Rose Cottage - Cozy and Comfortable with Ocean Views on Orr's Island

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Oceanview Cottage located in Beautiful Phippsburg! Common Dock and Wate, vacation rental in Bailey Island

Charming Oceanview Cottage located in Beautiful Phippsburg! Common Dock and Wate

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Comfortable & Cozy Getaway on Casco Bay, vacation rental in Bailey Island

Comfortable & Cozy Getaway on Casco Bay

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Oceanfront, Mere Point year round home Brunswick, vacation rental in Bailey Island

Oceanfront, Mere Point year round home Brunswick

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Waterfront apartment, vacation rental in Bailey Island

Waterfront apartment

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable cottage with million dollar view and short walk to stunning beach., vacation rental in Bailey Island

Adorable cottage with million dollar view and short walk to stunning beach.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sea Forever | Waterfront Home with Ocean-View Deck | Near Shops & Boat Launch, vacation rental in Bailey Island

Sea Forever | Waterfront Home with Ocean-View Deck | Near Shops & Boat Launch

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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