Discover a selection of 195 vacation rentals in Orrs Island, ME 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 outdoor grills and BBQs. Prices start at $140 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.
Top rated rentals — Orrs Island
Destination guide

Head to the culturally rich city of Orrs Island

Enjoy the culture and other features of Orrs Island. Renowned for its hiking, skiing and mountain views, this city welcomes all visitors. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

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

Exploring the natural features in Orrs Island

Whether you're an adventurous traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Orrs Island. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Casco Bay (5.5 mi / 8.9 km)
  • Wolfe's Neck Woods State Park (6.9 mi / 11 km)
  • Popham Beach State Park (8.8 mi / 14.2 km)
  • Thomas Point Beach (9.2 mi / 14.7 km)
  • Popham Beach (9.6 mi / 15.4 km)
  • Desert of Maine (11.1 mi / 17.8 km)
How to get there

Transportation options to and around Orrs Island

Fly into Portland Intl. Jetport Airport (PWM), the closest airport, located 19.2 mi (30.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Wiscasset, ME (ISS), which is 18.3 mi (29.5 km) away.

What are the top vacation rentals in or near Orrs Island?

Chic villas, tranquil houseboats and cozy cottages — everyone's ideal getaway is different. Whatever you're into, you're sure to find something to tantalize you among these top vacation rentals in Orrs Island:

  • "Maine Oceanfront Home": If you're on the hunt for a comfy space in Cumberland County, make yourself cozy here. It comes with 4 bedrooms and great amenities including nearby whale-watching activities and a phone.
  • "Premium Listing~ Westerly Ocean Views In Beautiful Harpswell": Put your luggage down and your feet up at this popular getaway in New England. It features 3 bedrooms, a TV, a nearby laundromat and more.

For even more great options, use the search bar at the top of the page to find the perfect Orrs Island vacation rental for you.

Can I find log cabins to rent in or near Orrs Island?

Choose your favorite log cabin from the many in or around Orrs Island and you'll soon be inside your timber-clad hideaway, drink in hand, relaxing by a crackling fire. But adventure is right outside your door too. These cabins offer a great mix of comfort and fun:

  • "Cozy Log Cabin - Walking Distance To Morse Mountain And 3 Miles From Popham Beach": This superb vacation home is a perfect base if you love playing in nature. Kayaking and mountain biking are two activities you can do in the area when you're not unwinding in your comfy cabin.
  • "Year Round Log Cabin Built In 1989 On Long Lake - 2": After a fun day of trying out some popular local pastimes, such as water skiing and kayaking, recharge your batteries at this in-demand property.

What are the top-rated vacation rentals for weekend getaways in or near Orrs Island?

If you've been busier than a hamster on an exercise wheel, you deserve to escape for a few glorious days. Skip out of work early on Friday and head for one of these weekend getaways in or near Orrs Island:

  • "Maine Oceanfront Home" is around 1 mile south of Orrs Island and the perfect place to recharge your batteries. You'll enjoy the convenient amenities here, including a microwave oven and heating.
  • Alternatively, throw a spare set of clothes into a small suitcase and make a beeline for "Percival” Penthouse Suite: Breathtaking Views". This well-liked getaway is about 16 miles southwest of Orrs Island and comes with heating and a fridge.

Can I find studio apartments for rent in and around Orrs Island?

You certainly can. If you want a small but stylish stay, you can't go wrong with a studio apartment. These compact properties exude charm and are often conveniently positioned in the middle of town. We suggest the following options in or near Orrs Island:

  • One of our favorite properties is "Chic One Bedroom Apartment In Portland's Arts District". Book a few nights at this popular stay and you'll have access to shopping and a garden.
  • "Historic Condo With Casco Bay Views" is another superb stay, providing all you could need for the perfect Orrs Island retreat. Handy amenities here include towels and a hair dryer.

Can I find short term rentals in or near Orrs Island?

Whether you're searching for a cabin just for you or a guesthouse big enough for the whole family, there's no shortage of short-term rentals in and around Orrs Island. These retreats make a comfortable base for a quick trip:

  • If you only need to stay a couple of nights, "Percival” Penthouse Suite: Breathtaking Views" is a terrific choice. It's not too far from the center of Orrs Island, so you'll be near all the top sights.
  • Another fantastic option is "Margaret” Penthouse Suite: Amazing Views Of Casco Bay". Round up your squad and enjoy a comfy stay close to the heart of Orrs Island.

What are the best romantic weekend getaways in or near Orrs Island?

Nothing says "I love you" quite like a romantic weekend together. If you'd like to spend a couple of relaxing evenings away with your partner, we've got some romantic getaways in and around Orrs Island that will whisk you off your feet:

  • Put on some love songs and chill together at "Henry” Penthouse Suite: Amazing Views". Around 16 miles from Orrs Island, this property has everything you need for a romantic weekend getaway, including winery tours and a nearby bay.
  • "Chic One Bedroom Apartment In Portland's Arts District" is another option that's bound to impress. It's about 17 miles from Orrs Island and has a nearby bay and winery tours.

What are the best large group vacation rentals in or near Orrs Island?

Big groups mean big fun. They also mean finding a place that'll effortlessly fit your entire squad. Browse our large group vacation rentals in or around Orrs Island and spend time with your favorite people under one roof:

  • Offering privacy, space and comfort, you'll get everyone's tick of approval at "New Well Built Elegant Home On The Water 2 Miles To Freeport". Up to 12 people can be accommodated at this escape which has 6 bedrooms, a kitchen and a fireplace. You'll find it around 8 miles to the northwest of Orrs Island.
  • "Beautiful House On The Harpswell Peninsula Over Looking Casco Bay" is another option that'll fit the whole crew. It's around 1 mile to the northwest of Orrs Island, has 7 bedrooms and accommodates up to 15 guests. A kitchen and a firepit are just a couple of things that'll help make your group vacation even more memorable.

What are the best houses for rent with a pool in or near Orrs Island?

A pool is often an essential amenity for any unforgettable vacation. Enjoy frolicking around or simply lazing by the water at one of these refreshing getaways in or near Orrs Island:

  • Top on our list of cool pool retreats is "Combo Unit, New House And Updated Cottage On Same Property". Traveling families will feel right at home here, with useful amenities like a dishwasher and childrens activities also at hand.
  • "Spectacular Oceanfront House On Maine Coast" is another great option. After you've enjoyed a dip with the fam, make the most of other conveniences like childrens activities and cable/satellite TV services.

What are the best large family vacation rentals in or near Orrs Island?

A family get-together should be one to remember. Whether you're planning an action-packed escape with the kids or a long-overdue family reunion, our large family vacation rentals in or near Orrs Island offer a comfy home away from home with ample space for everyone:

  • Sleeping as many as 11 guests in 4 bedrooms, "Maine Oceanfront Home" is the perfect place to vacation with the family. This popular retreat is 1 mile to the south of Orrs Island and has creature comforts that include a living room and a stereo.
  • Another great choice is "New Well Built Elegant Home On The Water 2 Miles To Freeport". This property is 8 miles northwest of Orrs Island and comes with coffee and tea making facilities, a microwave oven and more. With 6 bedrooms accommodating up to 12 people, there's no need to leave anyone off your guest list.

If you want to see some family-friendly attractions around the area, you won't have far to go. Children's Museum of Maine, Portland Observatory and Fort Williams Park offer fun for all ages.

Can I find family cabin rentals in or near Orrs Island?

Spending time with family is important, which is why we'll help you find a space where you can truly connect. Rent one of these family cabin rentals in or near Orrs Island and create wonderful memories with the people you love the most:

  • "Secluded Casco Bay Waterfront Cabin" - Enjoy fun and good times with your gang at this getaway, which is around 2 miles southwest of central Orrs Island. Coffee and tea making facilities and free toiletries are among its family-friendly amenities.
  • "Renovated, Family Friendly Home With Ocean And Golf Views" - This cabin is also ideal for families and is around 6 miles east of Orrs Island. Offering a stereo, a microwave oven and more, it'll get everyone's seal of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Orrs Island vacation rental that's perfect for your needs.