Bailey Island vacation rentals

We found 170 vacation rentals — enter your dates for availability

Select from 26 homes, 31 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.

Vacation rentals with weekly discounts - Bailey Island

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Find out more about Bailey Island

Why visit Bailey Island

  1. Stunning Ocean Views: Enjoy breathtaking vistas of the Atlantic Ocean, perfect for relaxation and photography.
  2. Quaint Fishing Villages: Explore charming local communities that showcase the essence of Maine's coastal lifestyle.
  3. Outdoor Activities: Engage in boat charters, hiking, and beachcombing, catering to adventure seekers and nature lovers.
  4. Rich Cultural Experiences: Discover historic houses and artistic retreats that highlight the island's cultural heritage.
  5. Cozy Accommodations: Choose from a variety of vacation rentals, including seaside cottages and inviting condos.

Popular types of accommodation in Bailey Island

If you're exploring vacation rentals in Bailey Island, rest assured we have a variety of options to suit your needs. The most popular accommodations include houses, apartments, and condos. Whether you’re looking for a cozy kitchen kitchenette, a charming Harpswell guest suite, or a rustic cabin, you'll find plenty of choices. Plus, don’t miss out on the amenities available in our Freeport rental units to enhance your stay!

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy during their stay on Bailey Island, perfect for families or groups.
  • Apartments: Offering a convenient and modern living space, apartments are a popular option for those wanting a home-away-from-home experience.
  • Condos: Combining luxury and convenience, condos provide excellent amenities and often stunning views of the coast.
  • Cottages: These quaint and cozy retreats are ideal for a charming getaway by the sea.
  • Cabins: For a rustic experience, cabins offer a unique immersion in nature, perfect for relaxation.**

Top attractions in Bailey Island

Bailey Island, Maine, is perfect for outdoor and beach vacations, offering stunning scenery and rich cultural experiences. Explore beautiful beaches, historic houses, and nearby national parks. Visitors can enjoy various activities, including boat charters, artistic retreats, and intimate weddings. Whether you're seeking relaxation or adventure, Bailey Island has something for everyone to enjoy.

  1. Casco Bay: A picturesque bay offering stunning outdoor scenery, perfect for beach vibes and water activities. Enjoy kayaking, sailing, or simply relaxing by the shore while taking in breathtaking views.
  2. Bailey Island Bridge: This historic bridge connects Bailey Island and showcases unique architectural features. It's a great spot to appreciate local culture and snap memorable photos of the stunning coastline.
  3. Bowdoin College: Located 12 miles away, this historic college boasts beautiful architecture and lush grounds. Explore the rich cultural heritage through its art galleries and museums.

Things to do recommended for couples

For a romantic getaway on Bailey Island, try paddleboarding at Paddleworks for an adventurous experience. Enjoy live music at Thompson's Point, or unwind at the luxurious Portland Club. Each offers a unique vibe to create unforgettable moments together.

Things to do recommended for families

Your family will love exploring Bailey Island, Maine! Enjoy a game at Hadlock Field, relax at Fort Williams Park, and indulge your sweet tooth at Wilbur's of Maine Chocolate Confections. Each spot offers unique experiences perfect for making lasting memories together.

Things to do recommended for groups

Explore the LL Bean Flagship Store for outdoor gear, enjoy shopping and dining at the Maine Mall, or catch a show at the State Theatre for a cultural experience. Each destination offers unique vibes perfect for group fun and togetherness.

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

If you're planning a trip with a group, family, or pets, or if you're interested in longer stays, be sure to adjust your filters to match your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Bailey 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 gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Bailey Island with young kids: Traveling with young children can present its own set of challenges. It's essential to prioritize their comfort and safety, along with seeking out age-appropriate 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 vacation wouldn’t be the same without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds to ensure that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Bailey Island: If you're searching for vacation rentals that offer discounts 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Bailey Island

Bailey Island offers a charming escape for outdoor enthusiasts and beach lovers alike. Experience stunning ocean views and explore quaint fishing villages that embody the essence of Maine's coastal chic. Whether you’re enjoying family-friendly activities or relaxing by the shore, this island promises a delightful blend of adventure and tranquility. Take in the picturesque scenery and immerse yourself in the warm, welcoming atmosphere of this beautiful destination.

  • Portland: Located 14 miles from Bailey Island, Portland is a vibrant city known for its rich cultural scene and stunning coastal views. Travelers flock to Portland for outdoor adventures, family-friendly activities, and picturesque scenery. The city offers an array of attractions, including beautiful beaches, family-friendly lakes, and a bustling arts scene featuring theaters and concert venues. Don't miss the chance to explore the Old Port district, where you can enjoy waterfront dining, boutique shopping, and local craft breweries.
  • West Harpswell: Just 2 miles from Bailey Island, West Harpswell is a charming neighborhood celebrated for its natural beauty and romantic ambiance. Visitors are drawn to its outdoor recreational opportunities, including scenic hiking trails and serene lakes. The coastal views are breathtaking, making it a perfect spot for a leisurely day trip. Explore the local beaches and bays, or enjoy a picnic in one of the many recreational areas. The peaceful environment is ideal for couples seeking a quiet retreat.
  • Orrs Island: A mere 3 miles from Bailey Island, Orrs Island is a picturesque destination known for its outdoor activities and scenic landscapes. This quaint community offers various water sports, making it a favorite for adventure seekers. Visitors can enjoy recreational areas perfect for family outings or educational experiences about local marine life. The island's beautiful beaches and tranquil lakes provide the perfect backdrop for relaxation and exploration. Don't miss the chance to soak in the stunning coastal charm that Orrs Island has to offer.

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 November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January26.4°F (-3.1°C)Light RainMostly SunnyLowSlightly High
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 SunnyAverageAverage
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 SunnyHighAverage
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 SunnyAverageSlightly Low

Booking with Vrbo is simple

Are you interested in saving money on your upcoming trip? Flexibility with your travel dates can really pay off, as prices tend to vary. Additionally, booking a longer stay often leads to substantial savings. To help you find the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group trip, you'll receive OneKeyCash™ on the full amount of your booking. Being the organizer truly has its benefits! Sign up for our One Key rewards program to unlock exclusive member discounts and earn OneKeyCash™ on eligible stays. Join us today and begin accumulating rewards!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy-to-use platform for planning your next getaway, allowing you to seamlessly create new trips, resume where you left off, or organize your travel plans. You can easily find the properties you’ve saved or booked, organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, just head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Bailey Island?
Cottages are the most popular style of vacation rental in Bailey Island, according to our data. Even if you have a different idea about what you'd like, Vrbo has properties in many shapes and sizes. Look over our options to find your ideal fit.
How much does it cost to rent a vacation rental in Bailey Island?
Season, length of stay and property type are some of the conditions that can affect the price of a vacation home. Simply add your dates of travel to find your ideal escape. From homey country cottages to sprawling villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Bailey Island?
The average price for a vacation rental by the beach in Bailey Island depends on when you'll be there and the size and type of property you're searching for. You can easily find prices on Vrbo by entering your travel dates and destination. Then use our filters to choose the number of bedrooms and amenities that you prefer, like a pool, WiFi and air conditioning.
What are popular rental amenities in Bailey Island?
Some of the most popular rental amenities people look for in Bailey Island include a barbecue grill, a firepit and a fireplace. Whether you're on a trip with family, buddies or even pets, Vrbo vacation properties feature the best amenities for ultimate relaxation with the people who matter most.
What are the top attractions for families in Bailey Island?
There's no room for boredom during your Bailey Island vacation with these family-friendly attractions:

  • Bailey Island Bridge
  • Cobwork Bridge

Can I find two-bedroom vacation rentals in Bailey Island?
Gather your family and enjoy total privacy and comfort in one of the 16 two-bedroom vacation homes Bailey Island has to offer.
Are there vacation rentals with WiFi in Bailey Island?
Bailey Island has 18 vacation rentals with WiFi, so you'll be able to stay connected while on vacation. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to posting pics on social media, these Vrbo homes make it a breeze to go online.
How old do you have to be to rent a vacation rental in Bailey Island?
The age limit can differ across properties on Vrbo, so be sure to check the rules of the vacation rental in Bailey Island you want. But usually, it's 16, 18 or 21.
How long can I rent a vacation rental in Bailey Island for?
The amount of time you can stay in a Bailey Island vacation rental for is up to each property. Simply put in your travel dates to browse options offering extended stays. They feature all the things you need to make your extended trip more comfortable and enjoyable, such as laundries and air conditioning. Some vacation homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Bailey Island?
Weekend break or extended vacation, Vrbo has some incredible bargains and discounts in Bailey Island that'll match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or check out what's just been added with one of our newly listed homes. Whatever you're after, you'll find the perfect place to stay --- without breaking the bank.

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