Bailey Island vacation rentals

We found 177 vacation rentals — enter your dates for availability

Select from 30 homes, 25 cottages, and other vacation rentals in Bailey Island to find one that's perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as parking and a washer and dryer. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.
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Find out more about Bailey Island

Why visit Bailey Island

  • Stunning coastal scenery: Bailey Island features breathtaking ocean views and rugged cliffs, perfect for nature lovers.
  • Outdoor activities: Engage in sailing, fishing, and beach outings to fully experience Maine's beautiful waterfront.
  • Charming neighborhoods: Explore picturesque areas that blend relaxation with local culture and coastal charm.
  • Family-friendly atmosphere: Enjoy a welcoming environment that caters to families seeking both adventure and leisure.
  • Variety of accommodations: Choose from cozy cottages, oceanfront rentals, and inviting condos for your perfect getaway.

Popular types of accommodation in Bailey Island

Bailey Island offers a delightful selection of vacation rentals, perfect for your getaway. Whether you’re seeking a private vacation home, a charming cottage, or a cozy condo, you'll find accommodations that suit your needs. Enjoy the stunning views from oceanfront cottages or unwind at the inviting Sea Escape Cottages. With options like Little Harbor nearby, your ideal vacation awaits. Explore Bailey Island vacation rentals and discover the perfect spot for your next adventure.

  • Houses: The top choice among travelers, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Cottages: These quaint and charming retreats provide a cozy atmosphere, ideal for couples or small families looking for a peaceful getaway.
  • Condos: A popular option, condos feature modern amenities and are often located near beaches, making them great for an enjoyable stay.
  • Apartments: Offering convenience and affordability, apartments are perfect for those wanting a home-like experience during their visit.
  • Cabins: Rustic and inviting, cabins provide a unique escape for nature enthusiasts seeking tranquility in a beautiful setting.**

Top attractions in and around Bailey Island

Bailey Island, Maine, is a perfect destination for outdoor enthusiasts and beach lovers. Explore stunning beaches, national parks, and picturesque island scenery. Visitors can enjoy activities such as sailing charters, fishing, and soaking in the beautiful Maine waterfront. Experience the local culture while taking in the breathtaking seaside views and charming fishing boats. Whether you're seeking relaxation or adventure, Bailey Island offers a delightful getaway.

  • Bailey Island Bridge: This historic bridge offers breathtaking views and a glimpse into the region's maritime culture. Its architectural charm and scenic surroundings make it a perfect spot for photography and leisurely strolls.
  • Casco Bay: Located a few miles from Bailey Island, Casco Bay is renowned for its stunning scenery and outdoor activities. Enjoy kayaking, sailing, or simply relaxing on the shores while soaking in the beautiful coastal atmosphere.
  • Popham Beach: About 11 miles away, Popham Beach features expansive sandy shores ideal for sunbathing and beachcombing. The gentle waves and picturesque views create a perfect setting for a day of relaxation by the ocean.

Things to do recommended for couples

For a romantic getaway in Bailey Island, consider a visit to the Portland Club, a luxurious private country club located 15 miles away. Enjoy intimate dining and stunning views, perfect for creating lasting memories with your loved one.

Things to do recommended for families

Families will love exploring the scenic tide pools at Land’s End, discovering local marine life. A visit to the charming Bailey Island Bridge offers stunning views, while the nearby beaches provide perfect spots for picnics and sandcastle building. Don’t miss the delicious lobster shacks for a true Maine experience.

Things to do recommended for groups

Groups visiting Bailey Island can enjoy a scenic lobster boat tour, explore the picturesque Coastal Maine Botanical Gardens, and savor fresh seafood at local eateries. Don't miss the chance to hike the stunning trails at nearby Land's End, offering breathtaking views of the Atlantic Ocean.

*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 Bailey Island

No matter if you're traveling with a group, spending time with family, bringing along your pets, or planning for an extended stay, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Bailey Island with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily apply filters for all of these options, and more, on Vrbo.
  • Traveling to Bailey Island with young kids: Traveling with young kids 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, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Bailey Island: For many families, a trip just isn't the same without their furry companions. If you relate to this, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer essentials like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Bailey Island: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right place. 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 criteria as well.

Where to stay in and around Bailey Island

Bailey Island, Maine, offers a picturesque coastal vacation with breathtaking ocean views and rugged cliffs. Embrace the family-friendly atmosphere while exploring charming neighborhoods nearby that blend relaxation with cultural experiences. Enjoy outdoor activities and soak in the stunning scenery that defines this unique Maine destination. Whether it's a day at the beach or a leisurely stroll along the rocky shoreline, Bailey Island promises unforgettable memories for every traveler.

  • West Harpswell: West Harpswell is a charming neighborhood located 2 miles from Bailey Island, offering visitors a delightful mix of romantic ambiance, outdoor adventures, and cultural experiences. This picturesque area boasts a variety of recreational venues, including theaters and arts centers, making it perfect for those who appreciate the arts. Nature lovers can enjoy beautiful beaches and serene lakes, perfect for family outings or peaceful retreats. The local beaches are ideal for sunbathing, swimming, and picnicking, while the recreational areas provide opportunities for hiking and exploring the stunning coastal landscape.
  • Giant's Stairs: Situated around Bailey Island, Giant's Stairs is a breathtaking coastal area that beckons travelers with its outdoor, family-friendly, and beach-centric experiences. Accessible via footpaths, this scenic spot features dramatic rocky shorelines and stunning ocean views. Families will enjoy the nearby family beach, perfect for a day of fun in the sun, while the tourist precinct offers various shops and eateries to explore. The natural beauty of Giant's Stairs makes it an excellent location for leisurely walks, beachcombing, and creating lasting memories with loved ones.
  • Giant's Stairs Trail: Located near Bailey Island, the Giant's Stairs Trail is an enchanting route that offers visitors a rich cultural experience along with picturesque views. As you traverse the footpath, you'll encounter historical landmarks, including a historic bridge and monument, adding a sense of history to your journey. This trail is perfect for those who appreciate the blend of nature and culture, providing a serene escape as you explore the beautiful coastal landscape. Hikers and history buffs alike will find this trail a rewarding adventure, showcasing the unique charm of the area.

Best time to go to Bailey Island

If you're planning a trip to Bailey 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
January26.4°F (-3.1°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
December33.1°F (0.6°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you seeking ways to save on your upcoming trip? Being flexible with your travel dates can lead to better deals, 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, utilize our filters to sort by price, location, and the type of vacation rental you prefer. We're here to help you find the perfect option.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, and manage your travel arrangements with ease. You can easily find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Soak up Bailey Island's alluring old-world vibe

Jutting off Maine's ruggedly beautiful coast into the deep blue Atlantic, Bailey Island lures visitors from far and wide thanks to its pristine shorelines, its sedate way of life and its beguiling old-world ambience. Bailey is located in the town of Harpswell, home to one of Maine's last remaining working harbors, which you'll invariably find packed with gently bobbing fishing boats and yachts. The island is also scattered with quirky boutiques and welcoming inns serving hearty home-cooked fare. Bailey Island vacation rentals range from cozy cottages perfect for a romantic getaway to sprawling family homes where you could host a big family get-together.

Bailey Island's natural wonders

As you approach the island, it's certainly worth stopping to marvel at the distinctive Bailey Island Bridge. Constructed in the 1920s, it was recognized in 1984 as a Historic Civil Engineering Landmark, as it was believed to be the only bridge on the planet made of granite cribstone. Once you've settled into your Bailey Island vacation rental, be sure to make a pit-stop at Mackerel Cove, a picture-postcard harbor where the shimmering water is ideal for swimming in the summer, and crabbing when it's cooler outside. For further spectacular coastal scenery, take a short hike to the Giant's Stairs, a dramatic rocky outcrop that dates back over 500 million years, where crashing waves can often be seen in the gleaming sunshine.

Shopping and seafood feasts on Bailey Island

Discerning shoppers will be enthralled by Bailey Island's array of independent stores, where you can pick up everything from one-of-a-kind artworks to exquisite hand-crafted jewelry to chic designer fashion. Bailey's dining scene is similarly captivating, Freshly-caught seafood naturally features prominently on many menus, so you can look forward to feasting on creamy clam chowder, buttery lobster rolls, decadent deep-fried clams or locally harvested oysters. If you fancy learning how your dinner was caught, join a lobster harvesting tour, where a local expert will talk you through the history of lobster trapping as you head out to sea, before showing you precisely how it's done.

Vivid seasons on Bailey Island

Bailey Island vacation rentals draw in big numbers of visitors during the sun-dappled months of summer. The days are long, warm and sunny, ideal for afternoons at sea or strolling down coastal paths. Winters, by contrast, are rather cold, with temperatures frequently tumbling below freezing and a fair amount of snowfall. Spring and fall are great times to visit, with mild to warm temperatures and fewer out-of-towners competing for prime accommodation.

Exploring the natural landscape of Bailey Island

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

  • Casco Bay (2.8 mi / 4.6 km)
  • Popham Beach State Park (9.8 mi / 15.7 km)
  • Popham Beach (10.7 mi / 17.3 km)
  • Desert of Maine (11.7 mi / 18.8 km)
  • Thomas Point Beach (12.1 mi / 19.4 km)
  • East End Beach (13.2 mi / 21.2 km)

Transportation to and around Bailey Island

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 17 mi (27.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away.

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