House in Bailey Island, ME
6 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this house rental
Charming , comfortable home, 2 full bedrooms plus 1 loft style bedroom, 2.5 bath, Very Close to Fresh Maine seafood!
Now accepting long term bookings for winter months~ November-May. Please inquire with manager for rates !
Cheerful, 3 bedroom, Cottage style home located on Bailey Island, Maine, on one of the peninsulas of Harpswell. Dog friendly, Three bedroom, 2.5 baths, custom cathedral ceilings, cozy living room, dining area, offering a well equipped, open kitchen with an island. The master bedroom is conveniently located on the main floor, presenting a king size bed as well as a connecting master bath and walk in closet ~ Up on the second floor, you will encounter two more sleeping spaces, one full bedroom, with a queen bed, and the other is a loft style bedroom with 2 twin beds. The lovely home has a fantastic outside deck, perfect of course for enjoying your morning coffee, or evening cocktails ! Just a super place to gather, and barbeque on the grill !
Convenient off road parking and is walking distance to many attractions. The quaint home is a stone's throw from magnificent ocean views, close to hiking trails, kayak rentals, candy shop, The Giant Stairs, art galleries, Land's End Gift Shop, Cook's Lobster House and more. You will be astounded with spectacular views while traveling over the world's only granite Cribstone Bridge! The bridge was listed on the National Register of Historic places in 1975, and was built back in 1927 in order to connect Orr's Island to Bailey Island. You are sure to find the freshest lobster on either of the islands !! Bailey Island is the perfect place for relaxation, and the home is perfect for a "base" for exploring the surrounding area. Just a hop away from Brunswick, which features Bowdoin College, The Maine State Music Theater, art museums, many great restaurants, shops, and groceries. Freeport, (home of the mother store for LL Bean), Portland, Boothbay, Bar Harbor, Wiscasset, Bath, are all great day trips with super shops and wonderful places to dine !
Cancellations will receive refund as stated in the policy, less any processing fees. This property can be viewed and booked on Vrbo, AirBnb, and Maine Coastal Connections, Harpswell, Maine.
You are sure to be delighted with all that this area has to offer ! We are excited to now be dog friendly,(one only), for an additional fee.
Rental Property includes but not limited to :
1 King size bed, 1 Queen bed, 2 single beds
2 full baths, one half bath
1 Smart TV, Roku, Internet
Fully equipped Kitchen/dining area/living room
Stove/Gas Range/Fridge/Dishwasher/microwave/Toaster/Coffee Maker
Propane Fireplace, which may or may not be in use at time of stay.
Linens/Towels /Pillows/Blankets provided / Toiletries to get you started
Outside Deck Chairs
Parking for up to 3 vehicles in driveway
Now accepting long term bookings for winter months~ November-May. Please inquire with manager for rates !
Cheerful, 3 bedroom, Cottage style home located on Bailey Island, Maine, on one of the peninsulas of Harpswell. Dog friendly, Three bedroom, 2.5 baths, custom cathedral ceilings, cozy living room, dining area, offering a well equipped, open kitchen with an island. The master bedroom is conveniently located on the main floor, presenting a king size bed as well as a connecting master bath and walk in closet ~ Up on the second floor, you will encounter two more sleeping spaces, one full bedroom, with a queen bed, and the other is a loft style bedroom with 2 twin beds. The lovely home has a fantastic outside deck, perfect of course for enjoying your morning coffee, or evening cocktails ! Just a super place to gather, and barbeque on the grill !
Convenient off road parking and is walking distance to many attractions. The quaint home is a stone's throw from magnificent ocean views, close to hiking trails, kayak rentals, candy shop, The Giant Stairs, art galleries, Land's End Gift Shop, Cook's Lobster House and more. You will be astounded with spectacular views while traveling over the world's only granite Cribstone Bridge! The bridge was listed on the National Register of Historic places in 1975, and was built back in 1927 in order to connect Orr's Island to Bailey Island. You are sure to find the freshest lobster on either of the islands !! Bailey Island is the perfect place for relaxation, and the home is perfect for a "base" for exploring the surrounding area. Just a hop away from Brunswick, which features Bowdoin College, The Maine State Music Theater, art museums, many great restaurants, shops, and groceries. Freeport, (home of the mother store for LL Bean), Portland, Boothbay, Bar Harbor, Wiscasset, Bath, are all great day trips with super shops and wonderful places to dine !
Cancellations will receive refund as stated in the policy, less any processing fees. This property can be viewed and booked on Vrbo, AirBnb, and Maine Coastal Connections, Harpswell, Maine.
You are sure to be delighted with all that this area has to offer ! We are excited to now be dog friendly,(one only), for an additional fee.
Rental Property includes but not limited to :
1 King size bed, 1 Queen bed, 2 single beds
2 full baths, one half bath
1 Smart TV, Roku, Internet
Fully equipped Kitchen/dining area/living room
Stove/Gas Range/Fridge/Dishwasher/microwave/Toaster/Coffee Maker
Propane Fireplace, which may or may not be in use at time of stay.
Linens/Towels /Pillows/Blankets provided / Toiletries to get you started
Outside Deck Chairs
Parking for up to 3 vehicles in driveway
Amenities at Conveniently located, spacious home located on Bailey Island in Harpswell!
Non-smoking
Pets allowed
Family friendly
Map of Bailey Island, ME
Ratings and reviews
10 / 10Outstanding·Nov 2025
The only complaint is that there was a sulfur smell to the hot whatever.
10 / 10Outstanding·Oct 2025
Well-stocked kitchen, open concept, lovely deck to relax, dog-friendly. Lots of local recommendations and communication with the host was great!
10 / 10Outstanding·Sep 2025
Beautiful place to stay… lots of fun… thank you
10 / 10Outstanding·Sep 2025
Highly recommend the Fair Winds as the perfect place to stay in Bailey Island. The place was Home & Gardens picture perfect. The host is a premier host and her property shows it. We loved sitting on the back deck and listening to the ocean and birds. The house was and easy walk to Crib Bridge, Cedar Beach, Mackerel Bay, and the general store. The kitchen is stocked with everything one would need to prepare dinners or there are a few local restaurants within walking distance. We loved the ambience of the house. It was perfect for our group of six.
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Top rated by guests
9.8Outstanding
(19 Ratings)
"The only complaint is that there was a sulfur smell to the hot whatever. "
Lucas L.Don't miss out! Price and availability may change
