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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Cottages in Bailey Island

Unique oceanfront home with a deck, tons of natural light, & amazing views
Interior

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (55)
"Beautiful lcation, private & quiet"
Unique oceanfront home with a deck, tons of natural light, & amazing views
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (2)
"Lovely location, quiet, serene, and the cottage is totally cute and comfortable. "
Enjoyable 1-bedroom rustic cottage in Southport.
Waterfront Cottage
Fridge, microwave, oven, stovetop

Waterfront Cottage

9.2 out of 10, Wonderful, (24)
"Better than expected. Great location."
Waterfront Cottage
Salty Breeze Cottage
Fridge, microwave, oven, stovetop

Salty Breeze Cottage

10.0 out of 10, Exceptional, (7)
"We absolutely loved this peaceful spot by the water! It’s a quiet location with great water access, and the property is very well managed and maintained. We’d love to return!"
Salty Breeze Cottage
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Outdoor spa tub

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (34)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Property grounds

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (27)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
The Outlet House, Comfortable Cottage
Fridge, microwave, oven, stovetop

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (41)
"We booked this to be near our daughter and grandchildren in Freeport. It is a great location, large interior, quiet location."
The Outlet House, Comfortable Cottage
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Interior

Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town

9.6 out of 10, Exceptional, (25)
"Convenient and cozy. Lovely wooded lot with views. "
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
Outdoor dining

Modern woodland privacy with ocean, trails, and lobster all in walking distance.

10.0 out of 10, Exceptional, (41)
"My friend and I felt very relaxed at this house. The beds were comfortable and the kitchen was stocked with most every cooking equipment needed. The host answered any question I had very quickly and supplied information about the surrounding area. It was a great place to unwind!"
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Beach

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

9.0 out of 10, Wonderful, (2)
"Perfect getaway for three adults. The weather cooperated so we were able to enjoy the lake and spent most of the weekend outside. The location is great and easy to access. The home is comfortable, camp style living. It could benefit from an updated living room chair, as the one there is missing any solid cushioning. The loft area is tight and not suitable for adults. Amenities are simple and neighbors are very close — albeit friendly, overall good stay and would return. "
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Terrace/patio

Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

9.6 out of 10, Exceptional, (66)
"Great spot"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Cute 2+ Bedroom Cottage
Fridge, microwave, oven, stovetop

Cute 2+ Bedroom Cottage

9.6 out of 10, Exceptional, (14)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage
Quaint Retro Ash Cove Cottage
Flat-screen TV, books, stereo

Quaint Retro Ash Cove Cottage

9.6 out of 10, Exceptional, (15)
"Chuck and Lynn were excellent hosts. We enjoyed our stay!"
Quaint Retro Ash Cove Cottage
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
TV, fireplace, DVD player, books

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.0 out of 10, Wonderful, (66)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Renovated home with water views, dock access, Linekin Bay Resort fun - dogs okay
Beach nearby

Renovated home with water views, dock access, Linekin Bay Resort fun - dogs okay

5.6 out of 10, (5)
"location was great. bed sheets/ covers were not clean. nice kitchen no outside chairs or deck to enjoy the Maine weather."
Renovated home with water views, dock access, Linekin Bay Resort fun - dogs okay
'Sprucewold' Boothbay Harbor Cottage w/ Deck
Exterior

'Sprucewold' Boothbay Harbor Cottage w/ Deck

9.8 out of 10, Exceptional, (15)
"Clean, great screened in porch, comfortable beds, nice kitchen and comfortable furniture in main room. The flower boxes were beautiful"
'Sprucewold' Boothbay Harbor Cottage w/ Deck
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Outdoor dining

'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!

9.8 out of 10, Exceptional, (10)
"Really enjoyed the house and location."
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (50)
"Cozy spot on a beautiful beach - hard to beat!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
Interior

Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!

Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
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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