Photo by The Maine Way of Life

Orrs Island vacation rentals

We found 228 vacation rentals — enter your dates for availability

Select from 17 homes, 14 cottages, and other vacation rentals in Orrs Island to find one that's perfect for your trip. Vacation homes provide the amenities you need and want for your family, friends, or furry companion, such as a fireplace and a washer and dryer. At the end of the day, you'll be able to choose a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Orrs Island

Showing deals for:Nov 14 - Nov 21

Image gallery for Full sized home

Private kitchen
9.8 out of 10 rating
Exceptional
(32 reviews)

Full sized home

Harpswell, ME

9% off
Price is $261
$1,829 for 7 nights
All fees included
Full sized home

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Orrs Island

Find out more about Orrs Island

Why visit Orrs Island

  1. Stunning Scenery: Enjoy breathtaking coastal views and natural landscapes perfect for outdoor enthusiasts.
  2. Beach Relaxation: Unwind on beautiful beaches ideal for sunbathing and swimming.
  3. Historic Exploration: Visit charming historic houses that reflect the island's rich history.
  4. Outdoor Activities: Engage in bird watching, sailing charters, and other recreational pursuits.
  5. Local Culture: Explore nearby neighborhoods showcasing local art and culture for a vibrant community experience.

Top attractions near Orrs Island

Orrs Island, Maine, is perfect for outdoor enthusiasts and beach lovers. Explore stunning scenery, relax on the beach, and visit historic houses. Enjoy activities like bird watching and sailing charters, or take day trips to local attractions. Whether you're seeking culture or adventure, Orrs Island offers a memorable vacation experience for everyone.

  1. Bowdoin College: This historic college, located 10 miles from Orrs Island, offers a glimpse into American education with its beautiful architecture and rich cultural vibes. Explore the campus and enjoy art exhibits and events that showcase the college's vibrant community.
  2. Casco Bay: Just 5 miles from Orrs Island, Casco Bay is perfect for outdoor enthusiasts. Enjoy stunning scenery, relaxing beaches, and opportunities for kayaking, sailing, and wildlife watching in this picturesque coastal setting.
  3. Bailey Island Bridge: Located 2 miles from Orrs Island, this historic bridge provides a unique cultural experience. Walk or drive across to enjoy breathtaking views of the surrounding water and landscape, making it a great photo opportunity.

Things to do recommended for couples

For a romantic getaway in Orrs Island, enjoy an adventurous day at Paddleworks with water sports, then indulge in luxury at the Portland Club, just 17 miles away. Cap off your evening with live music at Port City Music Hall, also 17 miles from your cozy retreat.

Things to do recommended for families

Families will delight in sweet treats at Wilbur's of Maine Chocolate Confections, enjoy a game at Hadlock Field, and explore the Portland Observatory for a unique learning experience. Each location offers a warm, family-friendly atmosphere perfect for making lasting memories together.

What do I need to keep in mind when booking a vacation in Orrs Island

If you're traveling with a group, as a family, bringing your pets along, or seeking extended stays, be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Orrs Island with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Orrs Island with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with having access to suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Orrs Island: For many, a family vacation wouldn’t be the same without their furry companion by their side. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Orrs Island: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search for an even better experience.

Where to stay near Orrs Island

Orrs Island, Maine, offers a delightful coastal vacation experience with its stunning outdoor scenery and family-friendly atmosphere. Explore charming nearby neighborhoods that showcase local art and culture while enjoying recreational activities. Whether you're seeking relaxation on the beach or an adventurous island connection, Orrs Island promises unforgettable memories. Discover the perfect blend of tranquility and vibrant community vibes for your next vacation getaway.

  • Great Island: Great Island, located a mile from Orrs Island, is a serene destination perfect for those seeking outdoor adventures and romantic getaways. This picturesque island features stunning beaches and tranquil lakes, inviting travelers to indulge in activities like hiking, swimming, and picnicking. With its natural beauty and charm, Great Island serves as an ideal spot for relaxation and exploration, offering breathtaking views and a peaceful atmosphere.
  • Bailey Island: Situated three miles from Orrs Island, Bailey Island is a captivating city known for its scenic landscapes and vibrant beach culture. Visitors flock to this island for its recreational areas and a variety of water sports, making it a perfect destination for families and adventure seekers alike. Enjoy the beautiful family-friendly beach, explore local shops, or simply take in the stunning coastal views while soaking up the sun.
  • West Harpswell: Located two miles from Orrs Island, West Harpswell is a charming neighborhood that offers a blend of outdoor beauty and romantic ambiance. This area is perfect for nature lovers, with access to scenic lakes and picturesque beaches. Visitors can enjoy recreational activities, catch a performance at the local theater, or take a leisurely stroll along the waterfront, making it an inviting place for relaxation and exploration.

Best time to go to Orrs Island

If you're planning a trip to Orrs Island, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudiness
January26.1°F (-3.3°C)Light RainMostly Sunny
February27.1°F (-2.7°C)Light RainMostly Cloudy
March33.6°F (0.9°C)Light RainMostly Sunny
April43.5°F (6.4°C)Light RainMostly Sunny
May53.2°F (11.8°C)Light RainMostly Sunny
June61.2°F (16.2°C)Light RainMostly Sunny
July68.0°F (20.0°C)Light RainMostly Sunny
August67.8°F (19.9°C)Light RainMostly Sunny
September61.9°F (16.6°C)Light RainMostly Sunny
October52.2°F (11.2°C)Light RainMostly Sunny
November41.5°F (5.3°C)Light RainMostly Sunny
December32.7°F (0.4°C)Light RainMostly Sunny

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect fit for your needs!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your total booking amount. Being the planner comes with its rewards! By participating in our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides you with a convenient platform to plan new trips, manage your existing plans, or review and organize your reservations. Your saved and booked properties are now categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

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.

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.

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 / 14.8 km)
  • Popham Beach (9.6 mi / 15.4 km)
  • Desert of Maine (11.1 mi / 17.8 km)

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.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Orrs Island?
Based on our data, cottages are the most desirable type of vacation property in Orrs Island. But of course, everyone's idea of an epic stay isn't the same. Vrbo has vacation rentals of all sizes and shapes, so you're bound to find your perfect match.
How much does it cost to rent a vacation rental in Orrs Island?
The average price for a vacation rental in Orrs Island is determined by several factors, including property type, length of stay and time of year. Whether you'd like a sprawling villa with space for extended family or a comfy cabin for just you and your sweetheart, just add your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in Orrs Island?
Prices for beach houses in Orrs Island differ depending on the type and size of the property and time of year you're traveling. Simply enter your dates of travel into Vrbo and the number of guests to view available options and prices. From there you can use our filter tool to narrow your search results by amenities, ratings, nearby activities and more.
What are popular rental amenities in Orrs Island?
The most popular rental amenities people search for in Orrs Island are a barbecue grill, a nearby waterfront and a beach view. Whether you're going on vacation with pals, family or even pets, Vrbo vacation rentals provide the best amenities for making new memories with the people closest to you.
What are the top attractions for families in Orrs Island?
Paddleworks will keep the kids amused during a trip to Orrs Island. You'll find this family-friendly attraction close to the center.
Can I find two-bedroom vacation rentals in Orrs Island?
Gather your nearest and dearest and relax in total privacy and comfort in one of the five two-bedroom vacation rentals Orrs Island has to offer.
Are there vacation rentals with WiFi in Orrs Island?
Orrs Island has 15 vacation rentals with WiFi, so you'll be able to stay connected during your trip. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to sending emails, these Vrbo homes make it easy to get online.
How old do you have to be to rent a vacation rental in Orrs Island?
The minimum required age is typically 16, 18 or 21. It can differ from property to property on Vrbo, so check the rules of your chosen Orrs Island stay before booking your stay.
How long can I rent a vacation rental in Orrs Island for?
The amount of time you can stay in an Orrs Island vacation rental for depends on the property. Simply put in your dates of travel to view options that offer long-term stays. They have the things you need to make your extended vacation more convenient and comfortable, such as kitchens and yards. Some Vrbo vacation homes may also offer weekly or monthly discounts, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Orrs Island?
Whether you've got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to find some great deals and discounts on Vrbo. From weekend trips to extended getaways, we've got the perfect space for your next Orrs Island escape.