Discover a selection of 160 vacation rentals in Orrs Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and air conditioning. Prices start at $189 per night, and houses and cottages are popular options for a stay in Orrs Island. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Orrs Island
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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.

Activities

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.

Weather

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.

How many vacation rentals are available around Orrs Island?

Our 2021 property listings offer a large selection of 160 vacation rentals around Orrs Island. From 149 house rentals to 67 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.