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New Rentals for 2019-2020!

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Long Term Winter Rentals

Looking for a home for the winter months? We have several properties that are av...

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**Due to COVID-19, we are working remotely for the time being. If you have an existing reservation, please email us at [email protected] and we will respond as soon as possible. If you are interested in making a reservation, per Governor Mills' mandate, we may only accept reservations with arrival dates after May 1, 2020, and reservations may be taken py phone, email or online.  We can be reached at [email protected], 207-833-5337 (office voicemail) or 207-798-9659 (cell). 

The Crew at MaineStay Vacations is working diligently to address all inquiries and concerns in a timely manner, and we appreciate your patience as we do so.  Please know that we wish you and yours health and safety during this pandemic.  Be safe everyone and we hope to SEA you very soon!**


Welcome to MaineStay Vacations

The Town of Harpswell in the Casco Bay region of Coastal Maine boasts narrow peninsulas and island chains that jut south in the Atlantic Ocean. Harpswell is comprised of areas known as Harpswell Neck, Cundy's Harbor, Great Island, Orr's Island and Bailey Island

Bracketed by Casco Bay to the west and Cundy's Harbor to the east, this area is reminiscent of Northern European fords-narrow strips of land and deep gorges of water interspersed with placid coves and harbors. Trips south from Brunswick on the mainland to the tips of the peninsulas and islands bring the vacationer over winding roads and through the wooded countryside, rewarding visitors at almost every turn in the road with a glimpse of water. Cottages perch on the shoreline or on the crests of ridges. Harbors are dotted with fishing and pleasure boats alike. Waves ripple onto the rocks in some areas and splash enthusiastically in other areas.

Lobstermen pull their traps in front of you, and the Casco Bay Ferry's Bay Cruises allow you to gain the perspective of the land from the water. There are many opportunities for recreation, shopping, museums and water-related activities. Grab a map and look at Casco Bay. Notice the tremendous amount of shoreline enjoyed by Harpswell. Take a look at the area pictures throughout this website and you'll have no trouble making the decision that this area simply must be seen!

If you prefer to reach us by phone for additional information, we will be happy to spend some time with you. We can "paint a picture" of each cottage, its relative location, the area and coastal Maine, so that whatever vacation rental property you choose is one that meets your expectations in every respect. We have included many links about the area in the "Local Area Guide"  tab above.

Once you've decided that this is the area of Maine in which to spend precious vacation days, click on the "Vacation Rentals" tab above to review the lovely properties that we have to offer. We look forward to either introducing you to this area or welcoming you back!

For additional information on MaineStay Vacations, please use the "About Us" tab above. Thanks for giving us the opportunity to serve your vacation needs!