Conveniently located, spacious home located on Bailey Island in Harpswell!

From

$414

/ night

Conveniently located, spacious home located on Bailey Island in Harpswell! - Image 1

Conveniently located, spacious home located on Bailey Island in Harpswell! - Image 2

Conveniently located, spacious home located on Bailey Island in Harpswell! - Image 3

Conveniently located, spacious home located on Bailey Island in Harpswell! - Image 4

Conveniently located, spacious home located on Bailey Island in Harpswell! - Image 5

Select dates to see prices and availability

From

$414

/ night

About this property

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...

Pet Friendly
Refrigerator
Coffee / Tea Maker
TV
Microwave
Hair Dryer

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Location

Harpswell, Maine

More location info

Guest reviews of Conveniently located, spacious home located on Bailey Island in Harpswell!

10

Exceptional

Based on 7 verified reviews

8

Amy W.

May 29, 2026

·

Stayed 4 nights

A very nice clean home with beautiful water views. We had all we needed for a relaxing four night stay on Baileys Island.

10

Lucas L.

Nov 9, 2025

·

Stayed 2 nights

The only complaint is that there was a sulfur smell to the hot whatever.

10

Kerry F.

Oct 16, 2025

·

Stayed 2 nights

Well-stocked kitchen, open concept, lovely deck to relax, dog-friendly. Lots of local recommendations and communication with the host was great!

10

Richard H.

Sep 17, 2025

·

Stayed 4 nights

Beautiful place to stay… lots of fun… thank you

10

Dennie C.

Sep 13, 2025

·

Stayed 2 nights

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.

Property Policies

Check-in instructions

Everything you need to know for a smooth check-in.

Check-in

Check-out

Check-in from 16:00

Before 09:30

FAQs about Conveniently located, spacious home located on Bailey Island in Harpswell!

Is parking available at the property?

Parking is available on-site with space for up to 3 vehicles in the driveway.

Does the property allow pets?

Pets are allowed, specifically dogs, with a limit of one pet per stay. An additional fee applies for bringing a pet.

What are the check-in and check-out times?

Check-in is at 16:00 and check-out is at 09:30. Early or late check-in/check-out may be available upon request.

What accessibility features does the property offer?

The property features step-free entrances and wheelchair-accessible facilities, making it suitable for guests with disabilities.

Where is the property located in relation to key landmarks?

The property is located on Bailey Island, near the beach and various attractions such as the Brunswick Naval Aviation Museum and Joshua L. Chamberlain Museum. It is a short distance from hiking trails, kayak rentals, and local dining options.

What are the policies for guests staying with children?

Children are allowed at the property, with no additional charge for ages 0-17.

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