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Orrs Island vacation rentals

We found 224 vacation rentals — enter your dates for availability

Select from 18 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:Jan 9 - Jan 16

Image gallery for The Beach House Bailey Island Maine

Aerial view
10 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)

The Beach House Bailey Island Maine

Bailey Island, ME

8% off
Price is $325
$2,273 for 7 nights
All fees included
The Beach House Bailey Island Maine

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Find out more about Orrs Island

Find out more about Orrs Island

Why visit Orrs Island

  • Stunning coastal scenery: Orrs Island boasts breathtaking views of the Atlantic Ocean, perfect for relaxation and outdoor activities.
  • Picturesque beaches: Enjoy beautiful beaches ideal for sunbathing, swimming, and beachcombing.
  • Rich local culture: Explore the charming harbor library and historic houses that reflect the area’s heritage.
  • Outdoor adventures: Discover nearby offshore islands and state parks, offering hiking, kayaking, and wildlife viewing.
  • Diverse accommodations: Choose from oceanfront cottages, private homes, and comfortable condos tailored to your vacation needs.

Popular types of accommodation in Orrs Island

If you're wondering about the best accommodations in Orrs Island, look no further. Our platform offers a variety of popular options, including houses, charming cottages, and comfortable condos. Whether you're searching for oceanfront cottages or several houses for a group getaway, Orrs Island has something for everyone. Plus, we provide transparent information on nearby hotels and island rentals to ensure you have a stress-free vacation experience.

  • Houses: The top choice for visitors, these spacious homes offer a comfortable and private setting for families or groups.
  • Cottages: Quaint and charming, cottages provide a cozy retreat, perfect for a relaxing getaway by the water.
  • Condos: These modern accommodations combine convenience and comfort, ideal for those seeking a home away from home.
  • Apartments: Offering flexibility and amenities, apartments are a great option for travelers wanting a local experience.
  • Cabins: Rustic and inviting, cabins provide a unique escape into nature, perfect for a peaceful vacation.**

Top attractions near Orrs Island

Orrs Island, Maine, is perfect for outdoor and beach vacations, offering stunning scenery and a variety of attractions. Visitors can explore picturesque beaches, historic houses, and nearby state parks, making it ideal for those seeking cultural and outdoor experiences. Don't miss the local island library for additional resources and insights about the area. Whether you're traveling solo or with family, Orrs Island promises a memorable getaway.

  • Bowdoin College: A historic institution known for its beautiful campus and rich cultural heritage, offering a glimpse into American education and architecture.
  • Casco Bay: A picturesque bay perfect for outdoor activities, boasting stunning scenery, sandy beaches, and opportunities for kayaking and sailing.
  • Bailey Island Bridge: An iconic historic bridge that connects Bailey Island, featuring breathtaking views and a unique blend of culture and history.

Things to do recommended for couples

For a romantic getaway in Orrs Island, try paddleboarding with Paddleworks for some adventurous fun. 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 escape.

Things to do recommended for families

Families can have a blast at Hadlock Field, just 17 miles away, for some exciting sports action. Satisfy your sweet tooth at Wilbur's of Maine Chocolate Confections, located 9 miles away, and explore the fascinating Portland Observatory, 16 miles away, for a blend of family fun and entertainment.

Things to do recommended for groups

Groups visiting Orrs Island can shop at the LL Bean Flagship Store, camp at the adventurous Desert of Maine, and enjoy a cultural evening at the Maine State Music Theater. Each location offers unique experiences that cater to families and friends alike.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip, whether it’s with friends, family, or pets, or if you're considering extended stays, be sure to set your priorities when searching. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Orrs Island with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor area for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Orrs Island with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities, like a private swimming pool. Additionally, keeping in mind how close you are to family-friendly attractions can make your trip even more enjoyable.
  • Taking your pets with you to Orrs Island: For many, a family vacation isn’t truly a vacation without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many pet-friendly homes offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Orrs Island: If you're seeking vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Additionally, think about including features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Orrs Island

Orrs Island beckons with its stunning coastal scenery and vibrant outdoor activities. Explore nearby offshore islands, unwind on picturesque beaches, and immerse yourself in the local culture. The charming harbor library offers a glimpse into the area's rich history, while the Atlantic Ocean provides a stunning backdrop for relaxation and recreation. Whether you're seeking a family-friendly retreat or a romantic getaway, Orrs Island and its surrounding neighborhoods promise an unforgettable vacation experience.

  • Bailey Island: Located 3 miles from Orrs Island, Bailey Island is a charming destination known for its stunning outdoor scenery and beautiful beaches. Visitors flock to this picturesque island to enjoy recreational activities such as kayaking, fishing, and beachcombing. Highlights include the serene family beach and tranquil lake, making it an ideal spot for relaxation and family-friendly fun. The local stores offer unique finds and snacks to enjoy while taking in the coastal views. The island's natural beauty and laid-back atmosphere provide an inviting escape for travelers seeking a seaside experience.
  • Great Island: Just 1 mile from Orrs Island, Great Island is a perfect getaway for those looking for a romantic and outdoor experience. This scenic island features beautiful beaches and serene lakes, making it an ideal location for picnics and leisurely strolls. The peaceful surroundings create a cozy atmosphere for couples and families alike. With its unspoiled nature and stunning waterfront views, Great Island is perfect for those wanting a quiet retreat while still being close to the attractions of the surrounding area.
  • West Harpswell: Located 2 miles from Orrs Island, West Harpswell is a delightful neighborhood that combines outdoor adventures with scenic beauty. Known for its recreational areas and vibrant local theater, this community offers a range of activities for both relaxation and entertainment. Outdoor enthusiasts can explore nearby lakes and beaches, while nature lovers can visit the local national state park for hiking and wildlife viewing. The enchanting scenery and friendly atmosphere make West Harpswell a must-visit spot for anyone looking to immerse themselves in the natural beauty of Maine.

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. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly SunnyLowSlightly Low
February27.1°F (-2.7°C)Light RainMostly CloudyLowSlightly Low
March33.6°F (0.9°C)Light RainMostly SunnyLowSlightly Low
April43.5°F (6.4°C)Light RainMostly SunnyAverageAverage
May53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
June61.2°F (16.2°C)Light RainMostly SunnyHighSlightly High
July68.0°F (20.0°C)Light RainMostly SunnyHighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
September61.9°F (16.6°C)Light RainMostly SunnyAverageAverage
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.5°F (5.3°C)Light RainMostly SunnyAverageAverage
December32.7°F (0.4°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to save money on your next getaway? Consider being flexible with your travel dates, as prices often fluctuate. Additionally, planning an extended stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and rental type. We're here to help you find the perfect vacation rental for your needs.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member 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 is your handy tool for planning trips, allowing you to easily start new adventures, return to previous plans, or manage your travel itinerary. You'll see all your saved or booked properties neatly organized under categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 best area to stay in Orrs Island when booking a vacation rental?
When considering a vacation rental in Orrs Island, Maine, a popular area to stay is along the waterfront near the Harraseeket River. This picturesque locale offers stunning views and easy access to various outdoor activities. Staying here allows you to enjoy the serene beauty of the river, making it ideal for kayaking or simply relaxing by the water.

Another great option is near the iconic Bailey Island Bridge. This area provides a charming coastal atmosphere, with several quaint shops and eateries within walking distance. You can also explore the nearby Land's End Gift Shop, which is a local favorite for unique souvenirs and delicious seafood options. The close proximity to these attractions makes it a delightful choice for visitors.

In terms of vacation rentals, Orrs Island offers a variety of properties that cater to different preferences, from cozy cottages to spacious homes. Many rentals are situated in scenic areas, ensuring that you can enjoy the stunning natural beauty of Maine while having all the comforts of home.
How much does it cost to rent a vacation home in Orrs Island?
Prices for vacation rentals in Orrs Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Orrs Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Orrs Island vacation house rentals?
You can find great discounts on house rentals in Orrs Island on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Orrs Island?
For renting a beach house in Orrs Island, Maine, travelers should explore the picturesque area near the Orrs Island Bridge, which offers stunning views of the surrounding waters and nearby islands. This region features charming seaside cottages that provide direct access to rocky shorelines and sandy beaches, superb for enjoying the coastal scenery. Many of these properties come equipped with amenities such as outdoor decks, ideal for soaking up the sun or enjoying evening barbecues, as well as fully stocked kitchens for convenient meal preparation.

Additionally, the nearby Harpswell Neck area is known for its tranquil beaches and scenic walking trails. Here, visitors can find lovely vacation rentals that often include features like private docks, superb for launching kayaks or enjoying a day of fishing. Many homes in this area also have cozy living spaces with fireplaces, making them great for relaxing after a day of exploring the beautiful coastline.

Exploring the local area, travelers can enjoy nearby attractions such as the scenic trails of the Harpswell Heritage Land Trust, which offer opportunities for hiking and birdwatching. Local seafood restaurants and quaint shops enhance the experience, providing a taste of the community's charm.
What is the most popular type of vacation rental accomodation in Orrs Island?
In Orrs Island, vacation houses are the most popular type of rental, with around 16 available. These properties are typically located near the waterfront, offering stunning views of the surrounding area. Most vacation houses come with fully equipped kitchens, spacious living areas, and outdoor decks or patios, great for enjoying the serene coastal environment. Additionally, there are about 13 cottages available, which provide a cozy and charming atmosphere, often featuring rustic decor, fireplaces, and easy access to nearby beaches and hiking trails. There are also several cabins and apartments scattered throughout the island, suiting travelers looking for a more intimate stay or a low-maintenance option.
Are there any family house rentals in Orrs Island?
On Orrs Island, Maine, families will find a variety of rental homes suitable for their needs, with around 25 options available. This picturesque area is known for its stunning coastal scenery and charming atmosphere, making it ideal for family getaways. Many of the homes feature spacious living areas, fully equipped kitchens great for preparing meals together, and outdoor spaces where children can play or where families can enjoy a meal al fresco.

Moreover, the island's proximity to local attractions adds to its appeal. Families can explore the nearby Harpswell Heritage Land Trust trails for hiking and nature walks, or take a trip to the scenic Bailey Island, famous for its lighthouses and rocky shorelines.
Can I find long-stay vacation rentals in Orrs Island?
A long-stay vacation rental in Orrs Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Orrs Island?
In Orrs Island, there are several pet-friendly house rentals available, making it a great destination for travelers wanting to bring their furry friends along. Many of these vacation rentals are located near the picturesque coastline, offering stunning views and easy access to the beach. Travelers can expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios where pets can enjoy the fresh air.

The area is known for its peaceful surroundings and natural beauty, with opportunities for outdoor activities such as hiking and exploring local parks. Nearby, the scenic Morse Mountain Conservation Area provides great trails for walking and enjoying the outdoors, which is great for pets. See all pet-friendly rentals in Orrs Island.
Are there any remote work vacation rentals in Orrs Island?
In Orrs Island, Maine, there are numerous options for remote work vacation rentals, with around 32 properties available. This picturesque island offers a serene environment, making it an ideal retreat for those looking to blend work and leisure. Many of these rentals come equipped with essential amenities for remote work, including Wi-Fi, dedicated desk spaces, and comfortable seating like desk chairs, which ensure a productive working atmosphere.

The island is known for its stunning coastal views and proximity to nature, providing opportunities for relaxation after work hours. Travelers can expect properties that feature cozy living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces to enjoy the fresh Maine air. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Orrs Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Orrs Island with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Orrs Island?
In Orrs Island, popular vacation rental amenities include WiFi, which allows guests to stay connected during their stay. Most rentals feature a fully equipped kitchen, enabling travelers to prepare their own meals and enjoy a home-cooked experience. Many properties also come with a coffee and tea maker for that superb morning pick-me-up, as well as patios where guests can relax and take in the serene surroundings. Additionally, some rentals are equipped with blenders, making it easy to whip up smoothies or cocktails.
How early should I book a Orrs Island vacation rental?
Book your Orrs Island vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Orrs Island?
In Orrs Island, visitors can enjoy a charming coastal atmosphere while exploring top attractions. The iconic Cribstone Bridge offers stunning views and serves as a picturesque connection between Orrs Island and Bailey Island. Nearby, the Land's End Gift Shop provides unique local crafts and souvenirs, great for those looking to take a piece of Maine home with them.

For nature enthusiasts, the nearby Harpswell Neck offers scenic walking trails and access to beautiful beaches, where visitors can soak in the serene ocean views. The local fishing industry is also a highlight, with opportunities to enjoy fresh seafood at nearby eateries.

Additionally, the area's proximity to the picturesque town of Brunswick allows for easy day trips to explore more attractions, including the Bowdoin College Museum of Art and the charming downtown area.
Can I change or cancel my Orrs Island home rental booking on Vrbo?
To find Orrs Island vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Orrs Island vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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