Photo by Colleen Johnson

Islesboro holiday lettings

We found 96 holiday rentals — enter your dates for availability

Discover a selection of 12 homes and other holiday rentals in Islesboro that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, including Wi-Fi and parking. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Showing deals for:17 Oct - 24 Oct

Why visit Islesboro

  • Stunning Natural Beauty: Islesboro boasts picturesque beaches and tranquil lakes, perfect for relaxation and exploration.
  • Outdoor Adventures: Enjoy a variety of activities in nearby state parks, ideal for hiking, kayaking, and family outings.
  • Charming Accommodation: Choose from delightful private vacation homes, quaint cottages, and spacious apartments for a memorable stay.
  • Rich Cultural Experience: Discover the local culture through quaint downtown areas and scenic surroundings.
  • Proximity to Myrtle Beach: Experience both relaxation and adventure with stunning coastal vistas just a short distance away.

Popular types of accommodation in Islesboro

If you're pondering what type of accommodation to choose in Islesboro, worry not, as we have it all sorted for you. Our most sought-after options include houses, charming cottages, and spacious apartments. Whether you're searching for cosy house rentals or convenient vacation rentals, we’re here to provide you with all the relevant information on Islesboro hotels and holiday homes to ensure a delightful stay.

  • Houses: The top choice for visitors to Islesboro, offering spacious and comfortable settings ideal for families or groups.
  • Cottages: A delightful option for those seeking a quaint and homely atmosphere, perfect for a relaxing getaway.
  • Apartments: A practical selection that provides the convenience of self-catering in a more urban setting.
  • Cabins: These rustic retreats are perfect for those wanting to immerse themselves in nature.
  • Chalets: A charming choice that combines comfort with a touch of alpine style, ideal for a unique experience.**

Top attractions near Islesboro

Islesboro, Maine, is a delightful destination for outdoor enthusiasts and those seeking stunning scenery. Visitors can explore beautiful beaches, tranquil lakes, and nearby state parks, perfect for a variety of activities. The area offers a rich cultural experience alongside ample opportunities for adventure, making it an ideal spot for families, couples, or solo travellers looking to unwind and enjoy nature.

  • Maine Maritime Academy: A historic institution located 5.0km from Islesboro, offering a glimpse into maritime culture and education. Explore its fascinating maritime heritage and enjoy the vibrant atmosphere.
  • Megunticook Lake: Situated 6.2km away, this picturesque lake is perfect for outdoor activities. With its beautiful beaches and stunning scenery, it provides a romantic setting for relaxation and adventure.
  • Camden Hills State Park: Just 5.0km from Islesboro, this national park features breathtaking views and various trails for hiking enthusiasts, making it an ideal spot for outdoor adventures.

Things to do recommended for couples

Islesboro offers delightful romantic experiences for couples. Visit Cellardoor Winery for a charming afternoon of wine tasting, or enjoy a fun round at Golfer's Crossing Mini Golf. Don't forget to dine at Stonington Sea Products, where you can relish delicious seafood in a warm, inviting atmosphere.

Things to do recommended for families

During your family vacation in Islesboro, enjoy delightful treats at Perry's Nut House, embark on an adventure at Oakland Park Bowling Lanes, and have a fantastic time at the ALLPLaY Family Entertainment Center, all within a short drive from your base in Islesboro.

Things to do recommended for groups

Experience the vibrant atmosphere at Camden Harbor Park and Amphitheatre, only 6.2km from Islesboro. Alternatively, explore unique crafts at Windsor Chairmakers, 3.1km away, or challenge your mates to a round of golf at the scenic Samoset Resort Golf Course, located 13.1km from the island.

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider the potential savings of booking a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Islesboro

Islesboro, Maine, offers a delightful escape for those seeking adventure and natural beauty. Nestled in Midcoast Maine, this charming island is perfect for outdoor enthusiasts and families alike. Explore the picturesque surroundings, including scenic beaches and quaint downtown areas, while indulging in leisurely excursions. Nearby, discover delightful destinations like Myrtle Beach, where you can enjoy a blend of relaxation and adventure amidst stunning coastal vistas.

  • Lincolnville: Located 3.1km from Islesboro, Lincolnville is a gem for outdoor enthusiasts and adventure seekers. This charming city offers stunning scenery with its picturesque hiking trails and well-maintained golf courses. Visitors can explore the nearby national parks, where you can hike amidst lush landscapes or relax by tranquil lakes. The area is perfect for those who appreciate the beauty of nature and wish to engage in a variety of outdoor activities.
  • Belfast: Situated 6.2km from Islesboro, Belfast is a vibrant city that beckons with its scenic views and recreational opportunities. The city is well-known for its extensive hiking trails and inviting parks, making it an ideal spot for those looking to immerse themselves in the great outdoors. Visitors can enjoy the local educational centres and recreational areas, as well as nearby national parks and lakes that provide a perfect backdrop for a day of exploration and relaxation.
  • Rockport: Located 6.8km away from Islesboro, Rockport is another delightful destination for nature lovers and adventure enthusiasts. This city is famed for its hiking trails and excellent golf courses, which attract visitors eager to enjoy the outdoors. The proximity to national parks and stunning lakes offers ample opportunities for exploration. Rockport’s charming landscape and vibrant community make it a wonderful place to unwind and experience the beauty of the Maine coast.

Best time to go to Islesboro

If you're planning a trip to Islesboro, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly CloudyModerately LowSlightly Low
February26.8°F (-2.9°C)Light RainMostly CloudyAverageAverage
March33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low
April42.4°F (5.8°C)Light RainMostly CloudyAverageSlightly Low
May51.8°F (11.0°C)Light RainMostly SunnyAverageAverage
June59.2°F (15.1°C)Light RainMostly SunnyModerately HighSlightly High
July65.8°F (18.8°C)Light RainMostly SunnyModerately HighSlightly High
August65.8°F (18.8°C)Light RainMostly SunnyModerately HighSlightly High
September60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyModerately LowAverage
December32.5°F (0.3°C)Light RainMostly CloudyModerately LowAverage

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

If you’re travelling with a group, family, or pets, or if you’re seeking longer stays, be sure to filter according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Islesboro with a group: Take into account the number of bedrooms required, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search on Vrbo to include all these options and more.
  • Traveling to Islesboro with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Islesboro: For many, a family holiday isn’t truly complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Islesboro: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include extras like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Effortless planning

Vrbo's ingenious Trip Board offers you a convenient way to plan new adventures, pick up from where you last stopped, or manage and review your travel arrangements. You can easily locate the properties you've saved or booked under Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your Islesboro getaway

Learn about the unique charm of Islesboro with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Islesboro

Do you want to find attractions to see in the city? Venture out of your cosy holiday rental and experience everything that makes Islesboro a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Cellardoor Winery (8.5 mi / 13.7 km)
  • Samoset Resort Golf Course (14.9 mi / 24 km)
  • Owls Head State Park (15.7 mi / 25.2 km)
  • Castline Golf Club (8.5 mi / 13.6 km)
  • Maine State Prison Store (20.5 mi / 33 km)
  • Dyce Head Foot Path (7.7 mi / 12.3 km)

Exploring the natural features in Islesboro

Whether you're an adventurous traveller or just want to take in the scenery, Islesboro is a great place to get out in nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Lincolnville Beach (5 mi / 8 km)
  • Belfast City Park (9.4 mi / 15.1 km)
  • Barrett's Cove Public Beach (9.5 mi / 15.3 km)
  • Megunticook Lake (9.6 mi / 15.4 km)
  • Camden Harbor Park and Amphitheatre (9.6 mi / 15.4 km)
  • Mount Battie (9.6 mi / 15.5 km)

Travelling to and around Islesboro

The nearest airport is in Rockland, ME (RKD-Knox County Regional), located 18.5 mi (29.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Bar Harbor, ME (BHB-Hancock County - Bar Harbor), which is 29 mi (46.7 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Islesboro?
Cottages are the most popular type of holiday rental in Islesboro, according to our data. Even if you've got a different idea about what you want, Vrbo has properties in loads of sizes and shapes. Explore our options to find your ideal fit.
How much does it cost to rent a holiday rental in Islesboro?
Several factors can affect what you'll pay for your holiday rental in Islesboro, like the type of property, length of stay and season. But, all our holiday homes have something in common --- excellent value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Islesboro?
Prices for beach houses in Islesboro vary depending on the type and size of the property and when you're travelling. Simply enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use our filter tool to refine your search by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday rentals in Islesboro?
With two properties that allow pets, your furry best friend can join in the fun on your Islesboro break. Use the filter tool to browse our pet-friendly holiday rentals and find a stay that's pawfect on Vrbo.
What are popular rental amenities in Islesboro?
A barbecue grill, a fireplace and a beach view head the list of most popular rental amenities in Islesboro. Whether you're taking to the road solo, with your spouse or a group of friends, Vrbo will help you find a holiday rental that fits your tastes with all the conveniences you're looking for.
Are there large group holiday rentals in Islesboro?
Yes, there are two holiday homes in Islesboro that can accommodate a group of five or more people. From family trips to a special event, these stays have ample space to chill out with the people that matter the most.
Are there holiday rentals in Islesboro that welcome kids?
Islesboro has two family-friendly holiday rentals. And discovering a stay that welcomes children is simple with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll get access to perks and amenities like living rooms, full kitchens and yards.
What are the top attractions for families in Islesboro?
There's a ton of exciting things to do and see with the family in Islesboro, such as:

  • Pitcher Pond
  • Warren Island State Park
  • Schoolhouse Museum

How old do you have to be to rent a holiday rental in Islesboro?
We advise checking with the Islesboro holiday property you want on Vrbo as age restrictions vary. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Islesboro for?
It really depends on the Islesboro property. To browse available options offering extended stays, just enter your travel dates and number of guests into Vrbo's search page. You can enjoy having the entire property to yourself, along with comforts such as a kitchen, air conditioning and a yard to run around in. Be on the lookout for long-term stays that offer weekly or monthly discounts.

More Holiday Rentals ideas

People also search for