Bailey Island holiday lettings

We found 159 holiday rentals — enter your dates for availability

Select from 22 homes, 28 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)
  • Paddleworks (1.7 mi / 2.8 km)
  • Ash Cove Pottery (1.4 mi / 2.3 km)
  • Wilbur's of Maine Chocolate Confections (9.7 mi / 15.6 km)
  • Gilsland Farm Audubon Center (12.5 mi / 20.1 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)
  • 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)
  • East End Beach (13.2 mi / 21.2 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 known as Great Island is an excellent choice. This picturesque neighbourhood boasts stunning views of the ocean and is close to some of the island's most charming attractions. One of the highlights is the iconic Cribstone Bridge, a unique stone bridge that connects Bailey Island to the mainland and offers breathtaking views of the surrounding waters. Additionally, the scenic Land's End Park provides a beautiful spot for walking and enjoying the coastal landscape.

Another delightful area to consider is the region around the Bailey Island General Store. This quaint location not only provides easy access to local provisions but also serves as a hub for exploring the island's rich maritime heritage. The proximity to the popular Cook's Lobster & Ale House makes it convenient to indulge in delicious seafood while enjoying the stunning ocean views.
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, Maine, visitors should focus on the picturesque coastal areas that offer stunning views and easy access to the Atlantic Ocean. The area around the popular Cribstone Bridge is a lovely spot, where you'll find charming cottages and beachfront homes that often come with amenities such as spacious decks for outdoor dining, fully equipped kitchens, and cosy living areas great for family gatherings. Many properties here also provide breathtaking ocean views and direct access to rocky shorelines, making them ideal for those looking to enjoy the natural beauty of the coast.

Another great option is the vicinity of Land's End, where you can find rentals that exude a quintessential New England charm. These properties often feature well-kept gardens, private patios, and outdoor grills, allowing guests to enjoy the fresh sea air. Additionally, being close to local shops and restaurants in the nearby town of Harpswell adds convenience for travellers.
What is the most popular type of holiday rental accomodation in Bailey Island?
In Bailey Island, cottages are the most popular type of holiday rental, with about 28 available throughout the area. These charming properties are often located close to the coastline, providing easy access to scenic views and nearby beaches. Most cottages typically feature fully equipped kitchens, cosy living spaces, and outdoor decks or porches great for enjoying the coastal breeze.
Are there any family house rentals in Bailey Island?
In Bailey Island, Maine, there is a wide selection of family-friendly holiday rentals available—around 51 in total. This charming coastal locale is great for families seeking a relaxing getaway by the sea. Many of the properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play and adults can unwind. Some homes even come with amenities such as private decks, barbecue facilities, and breathtaking views of the ocean.
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, there are several pet-friendly house rentals available, with around 22 options to choose from. The island is known for its picturesque coastal views and charming homes that often come with amenities like fully equipped kitchens, outdoor spaces, and sometimes even private decks that offer magnificent ocean vistas. Many of these rentals are designed for comfort, featuring spacious living areas and multiple bedrooms, making them suitable for families or groups travelling with pets.
Are there any remote work holiday rentals in Bailey Island?
In Bailey Island, Maine, there are a variety of remote work holiday rentals available, with around 57 options to choose from. This picturesque coastal destination is ideal for those looking to balance work and leisure. Many properties are equipped with essential amenities for remote work, including Wi-Fi, dedicated workspaces with desks and chairs, and even additional features like computer monitors for enhanced productivity. 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 typically include well-equipped kitchens, allowing guests to prepare their own meals. Many properties also feature patios where visitors can relax and enjoy the scenic coastal views. Additionally, rentals often come with essential appliances such as refrigerators and microwaves, along with cookware, dishware, and utensils to enhance the self-catering experience.
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.
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 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 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.

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