Your Stay in Orrs Island Starts Here

A trip to the Casco Bay area of Maine starts with a search for Orr's Island, Maine vacation rentals. It is a short 45-minute drive from Portland International Airport. From this base, you will enjoy the history and culture of the region. Orr's Island forms part of the town of Harpswell. Nearby, the Gulf of Maine beckons with waterfront recreation.

Nearby Cundy’s Harbor possesses a village charm unique even to this region. For generations of lobstermen, the harbor has proven a prime hunting ground. Tourism has flourished more recently. Travelers have discovered its rural charm and quiet pace of life. Part of the larger town of Bailey Island, the area features a number of attractions. Cozy wood-frame cottage houses remain present.

The area is notable for its beautiful, yet rugged, scenery. The peninsula offers some great views, with numerous coves to explore. Locals refer to one of the better-known coves as the Basin. It is located a little over a mile by boat or 22 miles by car northeast.

Vessels intending to sail around the harbor may wish to arrange a mooring at the Holbrook General Store. Summer marks the height of the tourist season, and vacationers will find the harbor a fine place to kayak and to swim. It bears repeating that the village is not a party spot. Rather, it is perfect for the vacationer who wants to leave the city behind in favor of a lush, relaxed environment.

Historical Sites

Orr's Island was named after Joseph Orr, who settled on the island with his brother in 1748. Start your exploration of this heritage at the Harpswell Historical Society Museum, open on Sundays during the summer. The museum includes colonial artifacts. Nearby, view the historical society's cattle pound. The town used to keep lost cattle here that had wandered off. Cattle caused damage to town gardens. Cattle owners had to pay a fine in order to retrieve their animals.

Arts and Culture

Harpswell hosts an annual summer concert series called "Bandstand by the Sea." It features the Harpswell Concert Band as well as other regional music groups.

In Brunswick, visit the Maine State Music Theatre. Attend a musical in the small, intimate auditorium space with comfortable seats.

Brunswick also offers the Bowdoin College Museum of Art. Visitors rave about the unique exhibits and admission is free.

Waterfront Recreation

Harpswell offers several beaches suitable for swimming. Kayaking, fishing, and sailing are other popular activities in this area. Local sailboat cruises take visitors around the many islands in the gulf. For more information, check the Harpswell city website.

Stay on Orr's Island, Maine, and enjoy nearby outdoor activities, historic sites, theater, music, and art museums. The area has a lot to offer while being convenient to a major airport.

Morning-Glory-Rental

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From $257/night
  • 8 Guests
  • 4 Beds
  • 3 Bath
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Sea-Scent

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From $199/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Captain's View

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From $214/night
  • 6 Guests
  • 3 Beds
  • 1.5 Bath
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Thorburn Cottage

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From $157/night
  • 6 Guests
  • 3 Beds
  • 1.5 Bath
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Haulin-Up-Place

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From $257/night
  • 7 Guests
  • 2 Beds
  • 2.5 Bath
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Nautical-Nest-Rental

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From $185/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Parciak-House

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From $400/night
  • 8 Guests
  • 4 Beds
  • 3.5 Bath
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Goldsmith-House

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From $257/night
  • 6 Guests
  • 3 Beds
  • 2 Bath
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Briggs-Cottage

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From $114/night
  • 6 Guests
  • 3 Beds
  • 2 Bath
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Bober Cottage

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From $157/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Zephyr

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From $186/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Gulls Rest

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From $171/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Little Harbor

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From $143/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Moon Shadows

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From $171/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Inner-Ledge

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From $243/night
  • 7 Guests
  • 4 Beds
  • 3.5 Bath
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Frostfish Cove

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From $200/night
  • 8 Guests
  • 4 Beds
  • 1.5 Bath
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Homeport

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From $214/night
  • 6 Guests
  • 3 Beds
  • 2 Bath
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Mingo Cove Getaway

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From $457/night
  • 8 Guests
  • 5 Beds
  • 4 Bath
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Garrison Cove Cottage

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From $120/night
  • 2 Guests
  • 1 Beds
  • 1 Bath
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