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Check prices for these dates

In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Cottages in Bailey Island

Boothbay Harbor Cottage Overlooking Mill Cove
Marina

Boothbay Harbor Cottage Overlooking Mill Cove

9.8 out of 10, Exceptional, (22)
"Clean, close to downtown."
Boothbay Harbor Cottage Overlooking Mill Cove
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, (48)
"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.
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, (41)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Terrace/patio

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

10.0 out of 10, Exceptional, (53)
"Beautiful views from a charming cottage with kind neighbors. Eclectic styled home which we enjoyed. Would stay again!!"
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Cozy Cottage with stunning views of Stover's Cove.
Interior

Cozy Cottage with stunning views of Stover's Cove.

9.8 out of 10, Exceptional, (7)
"We loved our time at the Cozy Cottage. They have the space well stocked with laundry detergent, dish soap, and even toiletries! All the communication was smooth and fast replies. I would recommend staying here if you are visiting Harpswell! "
Cozy Cottage with stunning views of Stover's Cove.
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Exterior

Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

9.6 out of 10, Exceptional, (39)
"Peaceful, beautiful property. Perfect for our honeymoon. Highly recommend this place and Gurnet Trading Post for seafood!"
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
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

9.2 out of 10, Wonderful, (68)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Terrace/patio

Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

8.6 out of 10, Excellent, (18)
"Very relaxing."
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Fridge, microwave, oven, stovetop

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!

9.8 out of 10, Exceptional, (32)
"Have stayed here two times over the years and it’s a great place for small families. We thoroughly enjoyed our recent visit."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Terrace/patio

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

9.6 out of 10, Exceptional, (24)
"Very nice all the basics covered. Close to the harbor, very quiet."
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Lilac Cottage - Near Georgetown Island - Midcoast Maine
Interior

Lilac Cottage - Near Georgetown Island - Midcoast Maine

10.0 out of 10, Exceptional, (24)
"We had a wonderful stay at this property. Our dogs loved being able to chase eachother around the yard"
Lilac Cottage - Near Georgetown Island - Midcoast Maine
Oceanfront Escape: Deck & Granite Steps to Shore
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Oceanfront Escape: Deck & Granite Steps to Shore

9.0 out of 10, Wonderful, (2)
"Everything was beautiful and we loved our stay!"
Oceanfront Escape: Deck & Granite Steps to Shore
Your own private island! Rustic and close to Nature.
Dining

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (32)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (11)
Enjoyable 1-bedroom rustic cottage in Southport.
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, (69)
"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, (18)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage
Renovated home with water views, dock access, - dogs okay
Fridge, microwave, oven, stovetop

Renovated home with water views, dock access, - dogs okay

6.6 out of 10, (8)
"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, - dogs okay
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

9.6 out of 10, Exceptional, (18)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Terrace/patio

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

10.0 out of 10, Exceptional, (8)
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (102)
"We sat and watched a major winter storm outside the window. Very exciting from within a cozy house. We enjoyed staying in a house where you could feel somebody's presence, rather than the "accessorized" vacation homes with welcoming signs from the Dollar store etc. Only thing lacking--place needs a new key box because the existing one is hard enough to use that it feels like it won't work. Gorgeous place!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
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

Quality Inn & Suites

Quality Inn & Suites

6/10 Okay
"Needs upgrading "
chris 2-night trip
Posted 1 day ago
Quality Inn & Suites

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