Bailey Island Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Bailey Island Vacation 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 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 CA $124
CA $226 total
includes taxes & fees
Aug 20 - Aug 21
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

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

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (53)
"This apartment was very clean, modern, and fairly private, located on a quite street, but still close enough to walk to shops, cafes, breweries. Only about half a mile from downtown. Would definitely stay again!"
Sunny Modern Oasis in Portland’s Trendy East End

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

10.0 out of 10, Exceptional, (64)
"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

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

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very good, (56)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

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 CA $435
CA $693 total
includes taxes & fees
Aug 20 - Aug 21
Fantastic Waterfront Views

Beachfront Delight with detached guesthouse, sunset views & private beach access

9.6 out of 10, Exceptional, (15)
"no place is a 10 BUT 8-9 is pretty good. Great Location to relax"
Beachfront Delight with detached guesthouse, sunset views & private beach access

Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

10.0 out of 10, Exceptional, (5)
"Our flight was delayed so we only got to enjoy this place from a quick nights sleep and morning breakfast, but we can't wait to go back. The view is so beaytiful, the host was very helpful given our late checkin, and gave us great recommendations for breakfast. Very friendly and everything you need to relax amongst the beauty of Maine."
The price is CA $419
CA $545 total
includes taxes & fees
Aug 24 - Aug 25
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

Large, light filled 4 bedroom house - walk to ocean and ferry

10.0 out of 10, Exceptional, (33)
"Comfortable place to stay and enjoy time with family. We enjoyed exploring Peaks Island and Portland. Everything we needed."
Large, light filled 4 bedroom house - walk to ocean and ferry

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!

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

10.0 out of 10, Exceptional, (1)
"Clean, comfortable. "
The price is CA $672
CA $1,225 total
includes taxes & fees
Sep 17 - Sep 18
Spacious 4-bedroom house located in the heart of Portland, ME.

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

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (101)
"Adorable place, roomy, quiet, upscale yet felt just like home. Will definitely stay again! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Modern Getaway by the Sea

The price is CA $587
CA $802 total
includes taxes & fees
Aug 20 - Aug 21
Modern Getaway by the Sea

Beautiful Oceanfront House- Stunning Water Views

9.4 out of 10, Exceptional, (12)
"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

Phenomenal Home on Coast of Maine

8.8 out of 10, Excellent, (42)
"Had a great stay. Killer views!!"
The price is CA $471
CA $737 total
includes taxes & fees
Aug 21 - Aug 22
Phenomenal Home on Coast of Maine

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10.0 out of 10, Exceptional, (60)
"Very clean, lots of room for gathering. Perfect location on a quiet street with great views of the lake. Plenty of towels, bedding, water, etc. Would come back!"
The price is CA $1,191
CA $1,766 total
includes taxes & fees
Sep 2 - Sep 3
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Bailey Island Hotel Reviews