Bailey Island holiday rentals

We found 180 holiday rentals — enter your dates for availability

Select from 31 homes, 27 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 enchants with its pristine beaches and picturesque ocean vistas, perfect for serene seaside walks.
  • Natural retreats: Explore charming national and state parks that offer a peaceful escape into nature.
  • Family-friendly charm: Ideal for all ages, the island provides leisurely outdoor pursuits and relaxing landscapes.
  • Local culture: Enjoy fresh seafood and vibrant art galleries that encapsulate the island’s unique character.
  • Scenic walking trails: Wander along serene pathways that reveal the true beauty of Bailey Island.

Popular types of accommodation in Bailey Island

Nestled in the charming Harpswell region, Bailey Island, Maine, offers a delightful array of holiday rentals, including private homes, cosy cottages, and inviting condos. This picturesque island is renowned for its stunning coastal views, scenic lighthouses, and serene walking trails. Explore the local charm through fresh seafood dining and vibrant art galleries, making Bailey Island the perfect destination for a memorable getaway filled with relaxation and adventure.

  • Private Holiday Homes: The top choice for visitors, offering ample space and a homely atmosphere for families and groups.
  • Cottages: Quaint and charming, these are perfect for a cozy retreat surrounded by nature.
  • Condos: Modern and convenient, ideal for those seeking comfort in a vibrant community.
  • Apartments: A practical option for couples or solo travellers looking for a city vibe.
  • Cabins: Rustic and idyllic, providing a true escape into the serene wilderness.**

Top attractions near Bailey Island

Bailey Island in Maine offers a delightful retreat for those who appreciate the great outdoors, stunning coastal scenery and sandy beaches. The island is perfect for enjoying natural attractions such as pristine beaches, charming national and state parks, and picturesque island vistas. Travellers can immerse themselves in the local culture and the beauty of nature, making it an ideal destination for a relaxed and scenic holiday.

  • Popham Beach: A serene stretch of shoreline offering soft sands and stunning coastal views, perfect for sunbathing, picnicking, and beachcombing. The gentle waves make it an ideal spot for families and relaxation.
  • Harrington House: This historic residence showcases the rich cultural heritage of Bailey Island. Visitors can explore its fascinating architecture and learn about local history, providing a glimpse into the island's past.
  • Seguin Island Lighthouse: A charming historic lighthouse that stands as a sentinel over the sea. Visitors can enjoy picturesque views of the coastline and the surrounding waters, making it a memorable spot for photography.

Things to do recommended for couples

Enjoy a romantic escapade on Bailey Island. Stroll hand-in-hand along scenic coastal paths, share a quiet picnic by the shore, and savour local seafood in charming bistros, creating unforgettable memories in this picturesque seaside retreat.

Things to do recommended for families

Families visiting Bailey Island can explore beautiful beaches and enjoy a range of local kid-friendly activities, including nature walks and interactive local museums, making their holiday a delightful and engaging experience.

Things to do recommended for groups

Discover Bailey Island's coastal charm with group cycling tours and scenic beach picnics, offering an immersive local experience in the quaint seaside village.

*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

If you're travelling with a group, family, pets, or seeking extended stays, be sure to refine your search with the appropriate priorities. Here are some helpful Stayz booking tips for you.

  • Traveling to Bailey Island with a group: Consider the number of bedrooms you may require, along with facilities such as a fully equipped kitchen or an outdoor area for group get-togethers. Fortunately, you can apply filters for all these features—and more—on Stayz.
  • Traveling to Bailey Island with young kids: Traveling with young children can be a demanding endeavour. It is essential to prioritise their comfort and safety, ensuring access to age-appropriate facilities, such as a private swimming pool. Additionally, it is advisable to consider the closeness to attractions that are welcoming to families.
  • Taking your pets with you to Bailey Island: For many, a family holiday isn’t complete without their four-legged companion. If that describes you, then consider exploring Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels at home.
  • Planning for a long term stay visiting Bailey Island: If you're seeking holiday rentals offering discounts for extended stays of a month or more, you've come to the right place. By utilising the appropriate filters, you can effortlessly locate and save on monthly rentals. You might also consider including a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Bailey Island

Bailey Island offers a delightful retreat with enchanting coastal scenery and family-friendly attractions. Explore its charming beaches and natural landscapes that provide a perfect backdrop for relaxing seaside strolls and romantic walks. The island's serene atmosphere invites travellers to enjoy a leisurely holiday immersed in nature, ideal for outdoor enthusiasts seeking both recreation and a peaceful escape.

  • Giant's Stairs Trail: Nestled around Bailey Island, Giant's Stairs Trail offers an inviting footpath that meanders through the local landscape, providing a distinct taste of culture-themed exploration. The route is dotted with historical landmarks, including a notable bridge and monument, which evoke tales of the past. This trail is ideal for those seeking to immerse themselves in an enriching cultural experience while enjoying the natural beauty of the coastal area.
  • Giant's Stairs: Located in the vicinity of Bailey Island, Giant's Stairs is renowned for its welcoming outdoor ambience. This footpath leads travellers to a family-friendly beach experience, enhanced by prominent attractions such as a tourist precinct and a well-loved family beach. It is a perfect destination for a leisurely stroll or a day out with family, blending the delights of nature with the charm of local landmarks.
  • Great Island: Situated 6km away from Bailey Island, Great Island is a naturally captivating island destination. It offers an outdoor adventure blended with scenic beauty and a beach experience. Visitors can explore the island's unique river and family beach, making it a delightful day trip for those eager to enjoy nature in its most pristine form.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 Stayz is a breeze

Looking to save on your upcoming break? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking a longer stay can result in considerable savings. To discover the ideal Stayz property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board offers a user-friendly platform where you can initiate new journeys, resume previous plans, or review and organise your upcoming adventures. Your saved or booked properties are neatly classified under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/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)
  • 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)
  • 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)
  • Wolfe's Neck Farm (7.5 mi / 12.1 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 most popular type of holiday home accommodation in Bailey Island?
The most desirable types of holiday homes in Bailey Island are cottages. Ready for more choices? Stayz has numerous options to match our guests' unique needs, so you'll see properties in lots of sizes and shapes. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a holiday home in Bailey Island?
Length of stay, property type and time of year are some of the conditions that can affect the price of a holiday home. Simply enter your travel dates to find your dream escape. From homey country cottages to expansive villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Bailey Island?
The average price for a holiday home close to the beach in Bailey Island depends on when you're visiting the area and the size and type of property you're looking for. You can find prices quickly and easily on Stayz by entering your destination and preferred travel dates. Then use our filters to pick the number of bedrooms and amenities that you need, like air conditioning, WiFi and a pool.
What are popular home amenities in Bailey Island?
A fireplace, a chef and a barbecue grill are the most popular home amenities in Bailey Island. Whether you plan to go on your own, with your significant other or a group of friends, Stayz will help you find a holiday home that matches your tastes with all the options you need.
What are the top attractions for families in Bailey Island?
Keeping the kids amused during your Bailey Island holiday is a snap with these family-friendly attractions:

  • Wolfes Neck Farm
  • Paddleworks
  • Wolfes Neck Woods State Park

Can I find two-bedroom holiday homes in Bailey Island?
Bailey Island has 15 two-bedroom properties for you to select from. Discover a holiday home with all the space and comfort you're looking for at a price that won't break the bank on Stayz.
Are there holiday homes with WiFi in Bailey Island?
Bailey Island has 16 holiday homes with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to scrolling social media, these Stayz homes make it easy to go online.
How old do you have to be to rent a holiday home in Bailey Island?
The minimum age is usually 16, 18 or 21. It can change across properties on Stayz, so look at the rules of your chosen Bailey Island holiday home before booking your stay.
How long can I rent a holiday home in Bailey Island for?
It's really down to the Bailey Island property. To view a list of options offering extended stays, just enter your travel dates and number of people into Stayz. You can look forward to having the entire place to yourself, along with comforts such as air conditioning, a kitchen and a backyard where the kids can play. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.