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Compare 408 Vacation Homes in Bailey Island with updated reviews, rates, and availability.

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Lakefront House

10.0 out of 10, Exceptional, (21)
" Thank you so much for sharing your lovely home with us. We had the perfect bachelorette weekend getaway! We would all definitely stay again! "
The price is AED 716
AED 2,838 total
includes taxes & fees
20 Jan - 21 January 2025
Lakefront House

Amazing riverfront home with private deck, views, private dock, & fireplace

9.4 out of 10, Exceptional, (40)
"Beautiful place! Perfect fit for us"
Amazing riverfront home with private deck, views, private dock, & fireplace

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

8.8 out of 10, Excellent, (15)
"Convenient to walking to town , great restaurants in the area for breakfast & dinner, house was perfect, comfortable, well maintained great off street parking and had everything we could ever had needed."
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Lofty cottage

9.4 out of 10, Exceptional, (39)
"We really enjoyed our time here has a beautiful view of the ocean. Had all the things needed to kayak and go out on the water. Nice and secluded. Had a fire pit, which was lovely to turn on In the evening. Would recommend this place and stay again"
Lofty cottage

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (10)
"Loved it! In"
Oceanfront Cabin-Castle in Maine Woods

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (114)
"This location is EVERYTHING!!! Right on the beach, cozy accommodations with spacious bedrooms was perfect for the 4 of us - with the 3rd bedroom, we could've included another couple! Host John was lovely!!!"
Charming 110-year former Inn 10' from the Ocean!

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

8.2 out of 10, Very Good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

10.0 out of 10, Exceptional, (69)
"Jaymes house had everything we could’ve need for our stay in boothbay. Well equipped for travelers most towels and bedding in the house appear to be new. Very responsive and accommodating house, perfect size for 2-3 couples to enjoy a weekend close to the harbor. "
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

5.6 out of 10, (5)
"The shared driveway was a challenge and the hike from the driveway to the house had was also a challenge. Additionally the window in one of the bathrooms did not work, the dishwasher was not secured and tilted when you put dishes in, one of the commodes ran constantly unless you jiggle. The kitchen garbage can is broken."
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach

10.0 out of 10, Exceptional, (10)
"We had a lovely week in this waterfront home. We enjoyed the views and the kids loved playing on the rocks out back. It was a nice location and short walk to Hendricks beach and the General Store. "
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach

Spectacular Waterfront Retreat Close To Portland!

10.0 out of 10, Exceptional, (46)
"Spent 2 glorious fall weeks at this West Bath property. This older, well updated house nicely accommodated the two of us. It was very comfortable and clean. We had everything we needed. There were plenty of dishes and flatware. We cooked in for most meals. There are black out curtains in the main bedroom, so you can really sleep in if you want to! We did! The backyard views are wonderful. Jennie’s Nubble has an active eagles nest. Lobster boats and sail boats were frequently in the area. The...
Spectacular Waterfront Retreat Close To Portland!

Stunning artist's retreat with ocean view & amazing deck, near Reid State Park

9.4 out of 10, Exceptional, (8)
"Amazing place. "
Stunning artist's retreat with ocean view & amazing deck, near Reid State Park

Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

10.0 out of 10, Exceptional, (19)
"Our stay was memorable and so enjoyable. There were 5 of us, 4 adults and 1 child. The location is in a nice little neighborhood, only steps from Crescent Beach. We could sit on our deck and see the ocean and sleep by the sounds of the waves. This property has so much to offer with three bedrooms, one of which is downstairs for this older stair challenged lady. It has three parking spots and a lovely fenced yard for the kids to play in. The cottage was very clean and the owner has it stocked...
Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
10.0 out of 10, Exceptional, (1)
"As you enter the house, you are entering the kitchen and looking at the most wall sized widow framed picturesque ocean waterfront view with islands included. We had two children with us and there was a has sack storage box filled with toys and a midsized toy kitchen that kept the children busy. The accommodations were cozy and homelike . We are already contemplating a warmer season return to enjoy the oceanfront amenities!"
Charming ocean-view cottage just 10 minutes from downtown Freeport shops

Luxury Carriage House a short stroll from town!

2.0 star property
10.0 out of 10, Exceptional, (5)
"Amazing location and beautiful little property. Everything was immaculate and welcoming, and we felt so taken care of, down to the small touches like just the coffee we like! Communication was great and timely, too. We'll definitely be back next time we are in Maine!"
The price is AED 1,098
AED 1,802 total
includes taxes & fees
29 Dec - 30 Dec
Luxury Carriage House a short stroll from town!

NEW LISTING! Prime City Living Townhouse by RedAwning

2.0 star property
8.0 out of 10, Very Good, (1)
"It was very convenient. "
The price is AED 745
AED 2,038 total
includes taxes & fees
12 Jan - 13 January 2025
NEW LISTING! Prime City Living Townhouse by RedAwning

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

9.2 out of 10, Wonderful, (81)
"This house is in perfect spot in Boothbay Harbor. Easy walk to town, right on the water. Everything about the house was perfect and exactly what we needed. "
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (35)
"Our party of 8 enjoyed our stay. The house is well equipped and stocked to get you started. Conveniently located to town and the Botanical Gardens. Plenty of outside space for kids to run around and play. It has a beautiful view of the cove but is very rocky. This didn't stop us from hunting hermit crabs and catching fish. The house is old but that gives it the Maine charm. "
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House
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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Other property types in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
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.