Bailey Island holiday lettings

We found 168 holiday rentals — enter your dates for availability

Select from 25 homes, 25 cottages and other holiday rentals in Bailey Island to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as air conditioning and a pool. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

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Why visit Bailey Island

  • Stunning coastal scenery: Bailey Island boasts breathtaking views and picturesque beaches, perfect for relaxation and photography.
  • Outdoor adventures: Engage in a variety of activities such as sailing trips, hiking, and exploring nearby national parks.
  • Charming local culture: Experience the island's vibrant culture through local markets, crafts, and community events.
  • Family-friendly atmosphere: Ideal for families, offering safe beach areas and numerous recreational opportunities for all ages.
  • Variety of accommodations: Choose from delightful vacation homes, cosy cottages, and comfortable condos to enhance your stay.

Popular types of accommodation in Bailey Island

You've chosen Bailey Island for your next getaway, and now it’s time to select your perfect accommodation. Explore the most sought-after options, including houses, charming cottages, and comfortable condos, all ready to make your stay memorable. Whether you're searching for a Bailey Island vacation rental or a cosy Maine cottage, we've got the ideal options to suit your needs.

  • Houses: The top choice for holidaymakers in Bailey Island, these homes provide a spacious and comfortable environment for families and groups.
  • Cottages: A charming option, cottages offer a quaint and cosy atmosphere, ideal for a picturesque getaway.
  • Condos: These modern residences provide convenient amenities and are perfect for those seeking a more communal living experience.
  • Apartments: A practical choice for couples or solo travellers, apartments offer a flexible and self-catering option.
  • Cabins: Rustic and inviting, cabins are a delightful retreat for those wanting to immerse themselves in nature.**

Top attractions in and around Bailey Island

Bailey Island, Maine, is ideal for outdoor and beach vacations, offering stunning scenery and a variety of attractions. Visitors can enjoy activities such as sailing trips and explore local points of interest including national parks and charming beaches. Whether you seek cultural experiences or outdoor adventures, Bailey Island provides a delightful getaway with opportunities for day trips and unique Maine sailing experiences.

  • Casco Bay: A stunning bay located 1.9km from Bailey Island, Casco Bay offers picturesque beaches and breathtaking scenery, perfect for outdoor enthusiasts and those looking to unwind in nature.
  • Bailey Island Bridge: This historic bridge, situated within Bailey Island, showcases unique cultural vibes and is an architectural marvel, providing a scenic connection to the island's rich history.
  • Bowdoin College: Located 7.5km away, Bowdoin College is a historic university known for its beautiful campus and cultural significance, making it a delightful stop for history and art lovers.

Things to do recommended for couples

For a romantic getaway on Bailey Island, consider an exhilarating paddle at Paddleworks, only 1.2km away. Indulge in luxury at the Portland Club, 9.3km distant, or enjoy an entertaining evening at Port City Music Hall, situated 8.7km away. Each offers a unique experience for couples.

Things to do recommended for families

Families can enjoy the excitement of Hadlock Field, just 9.3km away, or explore the captivating Portland Observatory, located 8.7km from Bailey Island. For a relaxing day out, Fort Williams Park, situated 8.1km away, offers beautiful scenery and wellness activities for all ages.

Things to do recommended for groups

Explore the LL Bean Flagship Store, just 6.2km from Bailey Island, for outdoor gear and apparel. Alternatively, head to the Maine Mall, 11.2km away, for shopping and entertainment, or enjoy family adventures at the Desert of Maine campground, located 7.5km from the island.

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

If you’re travelling with a group, family, pets, or looking for extended stays, it’s important to filter your options according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Bailey Island with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas suitable for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Bailey Island with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Bailey Island: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Bailey Island: If you're seeking holiday rentals with offers 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 as well.

Where to stay near Bailey Island

Bailey Island, a charming island destination in Maine, offers a delightful blend of outdoor adventures and stunning coastal scenery. Ideal for family-friendly holidays, visitors can indulge in beach relaxation and explore the vibrant local culture. Nearby areas enhance the experience with a perfect mix of recreation and tranquillity. From beautiful vacation rentals to picturesque views, Bailey Island promises a memorable getaway for those seeking both adventure and relaxation.

  • West Harpswell: West Harpswell is a picturesque neighbourhood situated a mere 1.2km from Bailey Island. This charming locale is renowned for its stunning outdoor scenery, making it a romantic getaway for couples and a delightful escape for nature lovers. Visitors can explore the local recreational areas and enjoy performances at the local theatre. Key attractions include a serene lake perfect for picnicking, beautiful beaches ideal for sunbathing, and the nearby national state park, offering numerous trails and wildlife viewing opportunities.
  • Orrs Island: Located 1.9km from Bailey Island, Orrs Island is a captivating city that embodies the essence of island living. This destination is a haven for outdoor enthusiasts, offering picturesque beaches and a plethora of water sports activities. Visitors can partake in recreational areas that provide education about the local environment and its marine life. Notable attractions include pristine beaches, a tranquil lake, and family-friendly shores, making it an excellent spot for both adventure and relaxation.
  • Great Island: Just 2.5km from Bailey Island, Great Island is another stunning destination known for its natural beauty and romantic allure. This island offers visitors an abundance of outdoor activities, with beautiful beaches that invite leisurely strolls and family gatherings. The local landmarks, including scenic lakes and family beaches, provide ideal settings for picnics and water activities. Whether you’re looking for a quiet escape or an adventure-filled day, Great Island promises a memorable experience amidst breathtaking surroundings.

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

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can result in significant savings. To discover the ideal Vrbo accommodation that fits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides an excellent area for you to plan new adventures, refine your existing arrangements, or manage your bookings with ease. Your saved or reserved properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover the features of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Take in the waterfront beauty of Bailey Island

Enjoy the monuments and other features of Bailey Island. Renowned for its island views, shopping and fishing, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Bailey Island

Are you hoping to discover top things to see and do during your stay? Venture out of your holiday home and check out everything that makes Bailey Island a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Land's End Gift Shop (1.3 mi / 2.1 km)
  • Gilsland Farm Audubon Center (12.5 mi / 20.1 km)
  • Ash Cove Pottery (1.4 mi / 2.3 km)
  • Paddleworks (1.7 mi / 2.8 km)
  • Wilbur's of Maine Chocolate Confections (9.7 mi / 15.6 km)
  • Brunswick Golf Course (12.7 mi / 20.4 km)

Exploring the natural landscape of Bailey Island

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Bailey Island is a great place to get outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Casco Bay (2.8 mi / 4.6 km)
  • Bates-Morse Mountain Conservation Area (8.3 mi / 13.3 km)
  • Popham Beach (10.6 mi / 17.1 km)
  • Desert of Maine (11.7 mi / 18.8 km)
  • Sand Beach (12 mi / 19.3 km)
  • Thomas Point Beach (12 mi / 19.3 km)

Transport to and around Bailey Island

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

Frequently asked questions

What is the best area to stay in Bailey Island when booking a holiday rental?
When considering a holiday rental in Bailey Island, Maine, the area around the southern end of the island is particularly appealing. This charming neighbourhood offers a picturesque coastal experience, with stunning views of the ocean and easy access to some of the island's best attractions.

One of the top highlights is the iconic Bailey Island Bridge, a lovely spot for leisurely strolls and taking in the beautiful scenery. Additionally, the nearby Land's End Gift Shop is a delightful place to explore local crafts and pick up souvenirs. The area features a variety of properties, from quaint cottages to larger homes, making it an ideal choice for families or couples seeking a romantic getaway.

Staying here allows you to immerse yourself in the serene beauty of the Maine coastline while being close to various outdoor activities, such as kayaking and hiking.
How much does it cost to rent a holiday home in Bailey Island?
Prices for holiday rentals in Bailey 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 Bailey 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 Bailey Island holiday house rentals?
You can find great discounts on house rentals in Bailey 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 Bailey Island?
For renting a beach house in Bailey Island, focus on the picturesque coastal areas near the shoreline, particularly around the scenic Harpswell Sound. The region is known for its charming cottages and seaside homes that offer direct access to the beach, with many properties featuring amenities such as spacious decks, outdoor dining areas, and private paths leading to the sandy shores.

The area near the Bailey Island Bridge provides stunning views of the surrounding waters and is a great spot for families or groups seeking a quintessential Maine beach experience. Here, you can find homes equipped with fully furnished kitchens, making it convenient for self-catering, as well as outdoor grills for summer barbecues.

In addition, the nearby Land's End area is renowned for its rocky coastlines and tidal pools, offering a unique environment for exploration. Many rentals in this vicinity come with amenities like fire pits for evening gatherings and easy access to local hiking trails that provide breathtaking views of the Atlantic Ocean.
What is the most popular type of holiday rental accomodation in Bailey Island?
In Bailey Island, cottages and holiday houses are the most popular types of holiday rentals, with around 96 of each available, providing a charming coastal experience. These properties often feature fully equipped kitchens, comfortable living areas, and outdoor spaces like decks or patios, great for enjoying the sea breeze. Additionally, approximately 20 apartments can be found, offering a more compact option for travellers. For those seeking a rustic retreat, several cabins and condos are also available, typically equipped with essential amenities for a comfortable stay.
Are there any family house rentals in Bailey Island?
On Bailey Island, Maine, families will find a delightful selection of holiday rentals, with around 49 properties available to suit various needs. The charming coastal community offers a picturesque backdrop, making it an ideal destination for family gatherings. Many of these homes feature spacious living areas, full kitchens for preparing family meals, and outdoor patios or decks where children can enjoy the fresh sea air.

In the nearby area, visitors can explore scenic points of interest such as the iconic Bailey Island Bridge and the beautiful beaches, superb for family outings. Additionally, some rentals may include amenities like private yards, barbecues, and even access to nearby hiking trails, enhancing the overall experience for guests of all ages.
Can I find long-stay holiday rentals in Bailey Island?
A long-stay holiday rental in Bailey Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Bailey Island?
In Bailey Island, travellers will find a selection of pet-friendly house rentals, with around 22 options available to choose from. Many of these holiday homes come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces superb for relaxing. Some properties even feature private decks or patios, allowing guests to enjoy the beautiful coastal views and fresh sea air alongside their furry companions.

The island itself is known for its stunning natural beauty, with nearby points of interest such as the scenic Bailey Island Bridge and the picturesque landings that provide excellent opportunities for walking and exploring with pets. Additionally, the local beaches are often welcoming to dogs, making it an ideal destination for pet owners looking to enjoy a seaside getaway.
Are there any remote work holiday rentals in Bailey Island?
In Bailey Island, there are ample options for remote work holiday rentals, with around 220 available in the area. This picturesque island, part of the larger Casco Bay, offers a tranquil environment for those looking to combine work with leisure. Many properties feature amenities specifically tailored for remote workers, such as dedicated desk spaces, comfortable desk chairs, and reliable Wi-Fi, often provided by third-party services.

Travellers can expect charming cottages and seaside homes with stunning views of the ocean, allowing for a refreshing backdrop during breaks. Some rentals also include outdoor spaces where one can unwind after a day of work, as well as fully equipped kitchens for convenient meal preparation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Bailey Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Bailey Island with parking available—perfect for families or travellers 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 Bailey Island?
In Bailey Island, popular holiday rental amenities include well-equipped kitchens, allowing travellers to prepare their own meals with ease. Many properties feature decks or patios, great for enjoying the coastal views and fresh sea air. Onsite parking is commonly available, making it convenient for those arriving by car. Additionally, visitors can expect coffee and tea makers in the rentals, providing a comforting start to the day. For those looking to stay active, fitness facilities are located nearby, offering options for exercise during their stay.
How early should I book a Bailey Island holiday rental?
Book your Bailey Island holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Bailey Island?
In Bailey Island, visitors can immerse themselves in the natural beauty and charm of this coastal destination. One of the top attractions is the iconic Giant's Stairs, a stunning rock formation that offers breathtaking views of the Atlantic Ocean and is great for photography. Nearby, the Bailey Island Bridge provides picturesque vistas and access to the surrounding areas.

For those interested in maritime history, the Cribstone Bridge is a unique structure made of granite and is a significant landmark in the area. The nearby landings, such as the Mackerel Cove, offer opportunities for boating and fishing, making it ideal for outdoor enthusiasts.

Additionally, visitors can explore local art galleries and enjoy fresh seafood at quaint restaurants that highlight the island's culinary offerings.
Can I change or cancel my Bailey Island home rental booking on Vrbo?
To find Bailey Island holiday 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 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 travellers 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 cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Bailey Island holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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