Bailey Island holiday rentals

We found 184 holiday rentals — enter your dates for availability
Select from 32 homes, 29 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:

  • Brunswick Golf Course (12.7 mi / 20.4 km)
  • Land's End Gift Shop (1.3 mi / 2.1 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)
  • Riverside Municipal Golf Course (15.9 mi / 25.6 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)
  • East End Beach (13.2 mi / 21.2 km)
  • Eastern Promenade (13.3 mi / 21.3 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Bailey Island holiday homes prices shown on Stayz?
Stayz 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.
Are there any Bailey Island holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Bailey Island holiday homes?
You can find great discounts on holiday homes in Bailey Island on Stayz, 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.
Can I change or cancel my Bailey Island holiday home booking on Stayz?
To find Bailey Island holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Bailey Island?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Bailey Island holiday home?
Book your Bailey Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bailey Island?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Bailey Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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