Destination guide

Get away from it all on Orr's Island

Located in Maine's rugged Casco Bay, Orr's Island is the centerpiece of an archipelago that forms the bulk of beguiling coastal community Harpswell. Visitors flock here from far and wide to soak up its intoxicatingly old-world atmosphere, to explore its picture-postcard fishing villages and to lounge on its unspoiled sandy beaches. Aside from an abundance of natural splendor, you'll also find a tempting array of independent gift shops, cozy pubs and family-run restaurants serving fresh, locally sourced lobster, crab, clams and other seafood staples. Orr's Island vacation rentals range from compact cottages to luxuriously spacious family summer houses, so you're bound to find one that suits your needs.

Things to do

Awe-inspiring arts around Orr's Island

Should you need a break from the sun or some shelter from the rain, the Bowdoin College Museum of Art, in nearby Brunswick, is home to one of the country's earliest collegiate art collections. This encompasses everything from ancient Assyrian antiquities to European Renaissance paintings to contemporary photography. A short walk away sits the Maine State Music Theatre, which presents a program of Broadway musicals each summer. Back in Harpswell, architecture buffs should set aside some time to marvel at the Bailey Island Bridge, the world's only bridge constructed from granite cribstone.


Hit the open seas around Orr's Island

Orr's Island is renowned throughout the United States and beyond as a boating hot spot. For a fun-packed family adventure, charter your own sail boat for the day and explore the glistening local waters at your leisure. If you're new to the pursuit, local sailing schools offer lessons suitable for all ages and abilities. Or if that sounds too much like hard work, you could join a lobstering tour and enjoy a scenic sea cruise whilst learning all about how the local delicacy is harvested. Back on dry land, Orr's Island is scattered with specialty shops, where you can pick up everything from handmade homewares to locally-made sweet treats.


Hazy summer days on Orr's Island

Orr's Island vacation rentals are highly sought-after during the peak summer months of June to August. At this time of year you can generally bank on long, warm days with plenty of sunshine. The shoulder months of May and September are also well worth considering – the weather is usually agreeably mild, and you may land a better deal on accommodation. Winters can be very chilly, but are often picturesque, with plenty of snowfall.

Natural features

Heavenly hikes around Orr's Island

Nature lovers will be in their element on Orr's Island. The whole of Harpswell is scattered with beautifully maintained walking trails, which might lead you over dramatic cliffs, across rocky coastlines or through dense, fragrant forests. As you soak up the tranquil vibe, the peace and quiet is likely only to be disturbed by chirping birds or scurrying chipmunks. The local waters are home to all manner of marine life. Join a boat trip and head out in search of playful seals or majestic whales.

Where to stay around Orr's Island?

Our 2019 property listings offer a large selection of 196 vacation rentals near Orr's Island. From 62 Cottages to 124 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Orr's Island for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Orr's Island?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Orr's Island:

  • Peaks Island: 77 vacation rentals
  • Bailey Island: 144 vacation rentals
  • Downtown Portland: 92 vacation rentals
  • Willard Beach: 29 vacation rentals
  • Willard: 31 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Orr's Island?

HomeAway offers a large selection of vacation rentals near lovely places in Orr's Island. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Paddleworks: 1,010 vacation rentals
  • Southern Maine Community College: 1,316 vacation rentals
  • Reid State Park: 932 vacation rentals
  • Crescent Beach State Park: 1,376 vacation rentals
  • Cape Elizabeth Light: 1,323 vacation rentals

But there are many other points of interest around Orr's Island listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Cottages in Orr's Island?

Yes, of course. HomeAway has 62 Cottages in Orr's Island. Our other popular types of vacation rentals in Orr's Island include:

  • Houses: 124 rentals available
  • Cabins: 62 rentals available
  • Bungalows: 62 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Orr's Island?

Yes, you can select your preferred vacation rental with pool among our 5 vacation rentals with pool available in Orr's Island. Please use our search bar to access the selection of vacation rentals available.

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