Holiday Homes in Bailey Island

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Featured Holiday Homes in Bailey Island

Our top choices for Bailey Island holiday homes

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

9.6 out of 10, Exceptional, (37)
"Very clean and had everything we needed for a nice long weekend with our pup in Boothbay Harbor"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Captain's Quarters 2BR Apartment. Walk to Everything!

8.6 out of 10, Excellent, (7)
The price is AU$391
includes taxes & fees
25 Aug - 26 Aug
Captain's Quarters 2BR Apartment. Walk to Everything!

Fantastic Waterfront Views

9.8 out of 10, Exceptional, (7)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
The price is AU$786
includes taxes & fees
31 Aug - 1 Sept
Fantastic Waterfront Views

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

7.6 out of 10, Good, (13)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is AU$255
includes taxes & fees
25 Aug - 26 Aug
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Spacious 4-bedroom house located in the heart of Portland, ME.

10.0 out of 10, Exceptional, (1)
"Clean, comfortable. "
The price is AU$1,383
includes taxes & fees
17 Sept - 18 Sept
Spacious 4-bedroom house located in the heart of Portland, ME.

On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.

10.0 out of 10, Exceptional, (65)
"We thoroughly enjoyed our stay. The owner is wonderful and accomodating. The property location is ideal for access to many attractions. "
On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (78)
"We had a great stay! Amazing weather and plenty of lobster."
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Oceanside escape 🌊 perfect family getaway!

9.8 out of 10, Exceptional, (18)
"Great location for proximity to Portland. Very clean and spacious."
Oceanside escape 🌊 perfect family getaway!

Modern Getaway by the Sea

The price is AU$906
includes taxes & fees
25 Aug - 26 Aug
Modern Getaway by the Sea

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (31)
"Place was amazing with an incredible view and fun layout. "
Oceanfront Cabin-Castle in Maine Woods

Shady Potts Point Cottage Cooled by Ocean Breezes

9.8 out of 10, Exceptional, (83)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes

Luxurious Penthouse with Modern Design in Downtown

9.8 out of 10, Exceptional, (12)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown

5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

10.0 out of 10, Exceptional, (144)
"This was our second stay at Beth’s home, and it certainly won’t be the last (as long as she’s willing to have us!) Everything is absolutely perfect. Beth is a thoughtful host, the location is perfect and the home is beautiful - you can’t go wrong!"
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (224)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Elegant and efficient Island home 4 miles from downtown Portland

8.0 out of 10, Very good, (1)
"Historic and charming home in a most interesting setting-- the community was a former military fort and barracks. Chat with neighbors on the front porch or watch wildlife and hang out in the backyard picnic tables. Comfortable beds and two full baths makes it good for group of 4-6 people. The golf cart is a godsend but there are bicycles and kayaks for land and water exploration. We didn't make it to the lovely looking pool or rec center for gym/bowling but they look like lots of fun. Rental and...
Elegant and efficient Island home 4 miles from downtown Portland

Beautiful Oceanfront House- Stunning Water Views

9.4 out of 10, Exceptional, (13)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (92)
"We enjoyed the view from this home and the location very much. Easy walkability to town and having Dunston’s right down the street was a fun perk. The communal spaces are small but cozy. The weather was rainy while we were there so we spent a lot of time nestled up reading and enjoying the view. My only complaint was there was no coffee provided—pretty small gripe and easily remedied!"
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

9.8 out of 10, Exceptional, (187)
"We loved watching from the back deck the tide going in and out. The kitchen was very well stocked. Convenient to shopping. Having access to a washer and dryer was a plus. "
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Beautiful house on the Harpswell Peninsula over looking Casco Bay

9.6 out of 10, Exceptional, (68)
"We had our wedding party stay at this property for our wedding at live well farm. It was beautiful and everyone enjoyed their stay. "
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Bay Haven. Comfort, deck & water access.

9.4 out of 10, Exceptional, (3)
"Beautiful location with great views of the water and expansive front porch with Adirondack chairs. Visited the local attractions like the Giant Stair Case, Lands End, sail boat trip, Maine Maritime Museum, Popham Beach. David and Mary, property managers, were very responsive to any of our requests. "
Bay Haven. Comfort, deck & water access.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bailey Island Hotel Reviews