Bailey Island vacation rentals

We found 164 vacation rentals — enter your dates for availability

Select from 26 homes, 29 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

Showing deals for:Nov 14 - Nov 21

Image gallery for Full sized home

Private kitchen
9.8 out of 10 rating
Exceptional
(32 reviews)

Full sized home

Harpswell, ME

10% off
Price is CA $302
CA $2,665 total
includes taxes & fees
Full sized home

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

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Find out more about Bailey Island

Find out more about Bailey Island

Why visit Bailey Island

  1. Stunning Ocean Views: Experience breathtaking vistas of Casco Bay and the Harpswell Islands, perfect for nature lovers.
  2. Outdoor Activities: Enjoy a variety of recreational pursuits, including sailing, beach lounging, and exploring nearby state parks.
  3. Charming Accommodations: Choose from cozy cottages, private vacation homes, and modern apartments for a comfortable stay.
  4. Family-Friendly Atmosphere: Engage in fun activities suitable for all ages, ensuring a memorable getaway.
  5. Relaxed Island Vibe: Unwind in a serene environment that combines cultural richness with natural beauty.

Popular types of accommodation in Bailey Island

Planning a getaway to Bailey Island? You're in for a treat! Discover the charm of this beautiful destination by choosing from a variety of vacation rentals, including houses, cozy cottages, and modern apartments. Whether you're looking for a serene sea escape or a family-friendly vacation home, Bailey Island has the perfect accommodations to meet your needs. Explore your options and make the most of your stay!

  • Houses: The top choice for visitors to Bailey Island, offering spacious accommodations perfect for families or groups.
  • Cottages: A charming and cozy option, ideal for those seeking a quaint and intimate getaway.
  • Apartment: Convenient and comfortable, apartments provide a home-like atmosphere for solo travellers or couples.
  • Condos: A modern alternative, condos often feature amenities and scenic views, making them a popular pick.
  • Cabins: Perfect for nature enthusiasts, cabins offer a rustic retreat amidst beautiful surroundings.**

Top attractions in Bailey Island

Bailey Island, Maine, offers a picturesque setting perfect for outdoor enthusiasts and beach lovers. Visitors can explore beautiful beaches, nearby state parks, and the charm of the island itself. With options for day trips, sailing adventures, private sails, and relaxing beach lounging, there's something for everyone seeking a cultural and outdoor experience. Enjoy the stunning scenery while making the most of your vacation on this delightful island.

  1. Casco Bay: Experience stunning outdoor beauty with picturesque beaches and vibrant scenery. Enjoy activities like kayaking, sailing, and observing marine life in this tranquil bay just 4.8km from Bailey Island.
  2. Bailey Island Bridge: Immerse yourself in the rich culture as you traverse this historic bridge. It connects Bailey Island to the mainland and offers spectacular views of the surrounding landscapes.
  3. Bowdoin College: Visit this historic institution located 19.3km away, known for its beautiful architecture and cultural significance. Explore the campus and enjoy its art collections and events.

Things to do recommended for couples

Experience romance on Bailey Island, Maine! Enjoy an adventurous day with Paddleworks, just 3.2km away, or indulge in live music at Port City Music Hall, 22.5km from your stay. For a touch of luxury, visit the Portland Club, located 24.1km away.

Things to do recommended for families

During your family vacation to Bailey Island, enjoy a thrilling game at Hadlock Field, relax at Fort Williams Park, and indulge in sweet treats at Wilbur's of Maine Chocolate Confections. These activities offer fun and memorable experiences for everyone in the family.

Things to do recommended for groups

Groups visiting Bailey Island can discover the iconic LL Bean Flagship Store 16.1km away, enjoy shopping and entertainment at the Maine Mall 30.6km away, or embark on an outdoor adventure at the Desert of Maine campground, located 19.3km from the island.

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 considering an extended stay, be sure to tailor your search according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Bailey Island with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Bailey Island with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, as well as provide age-appropriate amenities like a private swimming pool. Additionally, considering your proximity to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Bailey Island: For many, a family getaway isn’t truly complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Bailey Island: If you’re seeking vacation rentals with great offers 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, Maine, offers a delightful blend of stunning ocean views and family-friendly activities, making it an ideal vacation spot. Explore the picturesque Casco Bay and the surrounding Harpswell Islands, where you can soak in the natural beauty and enjoy recreational pursuits. With a relaxed atmosphere perfect for unwinding, you'll find a charming seaside experience that's both culturally enriching and rejuvenating, ensuring a memorable getaway for travellers from Canada and beyond.

  • West Harpswell: Located 3.2km from Bailey Island, West Harpswell is a charming neighborhood that offers stunning outdoor scenery and a romantic atmosphere. Visitors can enjoy recreational activities in the area, including hiking and exploring tranquil beaches. The local theatre is a great spot for catching live performances. Key attractions nearby include picturesque lakes and pristine beaches, making it an ideal destination for nature enthusiasts and couples seeking a peaceful getaway.
  • Orrs Island: Situated 4.8km away from Bailey Island, Orrs Island is a beautiful city renowned for its natural island features and outdoor recreational opportunities. This destination is perfect for beach lovers and those looking to engage in various water sports. With family-friendly beaches and scenic lakes, Orrs Island invites visitors to relax and enjoy the coastal charm. Educational attractions and recreational areas enhance the travel experience, making it a fantastic place for families and adventure seekers alike.
  • Great Island: Just 6.4km from Bailey Island, Great Island is another stunning natural gem. Known for its captivating beaches and romantic settings, this island is perfect for outdoor enthusiasts looking to explore the rugged coastline. Relax on the sandy shores or take in breathtaking views of the surrounding landscape. With lakes and beautiful beaches nearby, Great Island promises a refreshing escape for those seeking tranquility and adventure in a picturesque setting.

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 Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, opting for a longer stay can result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform for planning your travels. You can easily create new trips, resume planning from where you left off, or view and organize your existing plans. Your saved or booked properties will be neatly categorized into Potential, Upcoming, or Current Trips for your convenience. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/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 vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Bailey Island

Do you want to find things to do during your stay? Venture out of your cozy vacation rental and check out everything that makes Bailey Island a fun spot to vacation. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 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 (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)

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 best area to stay in Bailey Island when booking a vacation rental?
When considering a vacation rental on Bailey Island, Maine, the best area to stay is often around the picturesque village of Cook's Corner. This charming neighbourhood offers a delightful coastal atmosphere and easy access to some of the island's top attractions. One popular point of interest nearby is the iconic Cribstone Bridge, a stunning granite bridge that connects Bailey Island to the mainland and is a fantastic spot for photography and leisurely walks.
How much does it cost to rent a vacation home in Bailey Island?
Prices for vacation 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 travelling 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.
Are there any discounts for Bailey Island vacation 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 explore the picturesque coastline that characterises the area. The region around the iconic Bailey Island Bridge offers stunning ocean views and easy access to the beach. Many properties in this vicinity come equipped with amenities such as spacious decks for outdoor dining, well-appointed kitchens for self-catering, and cosy living areas superb for relaxing after a day spent by the sea.

Additionally, the area near Land's End and the Cribstone Bridge features charming cottages and homes that often boast direct beach access or proximity to scenic walking paths along the coast. These rentals typically include essentials like Wi-Fi, laundry facilities, and outdoor grills, making them ideal for families or groups looking to enjoy a seaside getaway.
What is the most popular type of vacation rental accomodation in Bailey Island?
In Bailey Island, cottages are the most popular type of vacation rental, with about 28 available throughout the area. These charming properties often feature rustic designs, fully equipped kitchens, and cozy living spaces, making them superb for a relaxing getaway by the coast. Many cottages also provide outdoor seating areas or decks, allowing guests to enjoy the stunning views of the surrounding ocean and landscape.
Are there any family house rentals in Bailey Island?
In Bailey Island, Maine, there are numerous family-friendly house rentals available, with around 51 options to choose from. This charming coastal locale is superb for families seeking both relaxation and adventure. Many of these homes boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor decks for enjoying the stunning views of the ocean. Some properties even include amenities like private gardens and game rooms, ensuring entertainment for all ages.
Can I find long-stay vacation rentals in Bailey Island?
A long-stay vacation 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, providing a welcoming environment for travellers with furry companions. Many of these rentals offer amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, ideal for families or groups looking to enjoy a coastal retreat.
Are there any remote work vacation rentals in Bailey Island?
In Bailey Island, Maine, there are numerous remote work vacation rentals available, with around 57 options to choose from. The picturesque coastal area provides a serene backdrop for those looking to balance work and leisure. Many of these properties come equipped with essential remote work amenities, including Wi-Fi, desk spaces, and comfortable chairs, ensuring a productive environment. Some rentals may also feature dedicated office areas or additional technology, such as computer monitors, allowing for a seamless work experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Bailey Island vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
Book your Bailey Island vacation 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 vacation 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 vacation 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 vacation 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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