Photo by Colleen Johnson

Islesboro holiday homes

We found 87 holiday rentals — enter your dates for availability
Discover a selection of 8 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.

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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)
  • Perry's Nut House (9.9 mi / 16 km)
  • Savage Oakes Vineyard and Winery (18.3 mi / 29.4 km)
  • Maine State Prison Store (20.5 mi / 33 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)
  • Camden Harbor Park and Amphitheatre (9.6 mi / 15.4 km)
  • Mount Battie (9.6 mi / 15.5 km)
  • Laite Memorial Beach (9.7 mi / 15.6 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 best area to stay in Islesboro when booking a holiday rental?
When considering the best area to stay in Islesboro, Maine, for a holiday rental, the community of North Islesboro is particularly appealing. This area offers a serene atmosphere, making it ideal for those seeking a peaceful getaway. North Islesboro boasts an array of charming properties, with many located near the coastline, providing stunning views of the water.One of the top attractions in North Islesboro is the beautiful Sandy Point Beach, superb for leisurely strolls or picnics. The beach's tranquil waters are also great for swimming during the warmer months. Additionally, the Islesboro Historical Society is a must-visit for those interested in the local heritage, showcasing fascinating exhibits about the island's past.With a variety of properties available, from quaint cottages to larger homes, North Islesboro offers something for everyone, ensuring a memorable stay in this picturesque part of Maine.
Where are the best areas for renting a beach house in Islesboro?
For renting a beach house in Islesboro, consider the picturesque waterfront properties along the eastern shore, particularly near the village of Islesboro itself. This area offers charming cottages and larger houses with stunning views of Penobscot Bay. Many of these rentals come with amenities such as private docks, outdoor seating areas, and fully equipped kitchens, making them great for families or groups looking to enjoy a seaside getaway.Another appealing option is the area near the ferry terminal, where you can find beach houses that provide convenient access to local shops and restaurants. These properties often feature spacious living areas and outdoor decks, ideal for soaking up the coastal atmosphere.Additionally, the northern part of the island, close to the scenic trails of the Islesboro Island Trust, offers a more tranquil setting with beach houses surrounded by nature. Many of these rentals include amenities like fire pits, grills, and easy access to secluded beaches, great for those wanting to explore the island's natural beauty.
What is the most popular type of holiday rental accomodation in Islesboro?
In Islesboro, holiday houses are the most popular type of holiday rental, with about 28 available across the island. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas—ideal for enjoying the stunning coastal views. Additionally, there are several apartments, cottages, and cabins that provide alternative options for travellers seeking a more intimate or rustic experience. Many of these rentals are situated near the waterfront, offering easy access to the island's beautiful beaches and scenic walking trails.
Are there any family house rentals in Islesboro?
In Islesboro, Maine, there are several family-friendly house rentals available, making it a wonderful spot for gatherings. The island offers a tranquil atmosphere with beautiful coastal views, great for reconnecting with loved ones. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.Visitors can also enjoy nearby attractions like the picturesque beaches and nature trails, providing opportunities for outdoor activities such as hiking and swimming. The local community is known for its charming character, with quaint shops and eateries that reflect the island's unique culture.
Are there pet-friendly house rentals in Islesboro?
In Islesboro, there are several pet-friendly house rentals available, providing a wonderful option for travellers looking to enjoy a getaway with their furry companions. Many of these holiday homes feature amenities such as spacious living areas, well-equipped kitchens, and outdoor spaces like decks or gardens, superb for relaxing after a day of exploration.The island is known for its serene beauty and offers easy access to pet-friendly beaches where your dog can enjoy the sand and surf. Additionally, there are picturesque walking trails and parks in the area that welcome pets, allowing for enjoyable outings amid the stunning Maine landscape.
Are there any remote work holiday rentals in Islesboro?
In Islesboro, Maine, there are a variety of remote work holiday rentals available, with around 48 properties suiting those needing a productive environment. This picturesque island offers a tranquil setting for remote workers, surrounded by stunning coastal views and natural beauty. Many of the rentals feature amenities such as high-speed internet and free Wi-Fi in-room, ensuring that you can stay connected while enjoying the serene surroundings.The island is known for its charming coastal landscape, with opportunities for outdoor activities such as hiking and exploring the local beaches. Properties often come equipped with comfortable workspaces, spacious living areas, and well-equipped kitchens, allowing for a balanced blend of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Islesboro?
In Islesboro, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals, and decks or patios for enjoying the stunning surroundings. Many properties are pet-friendly, making it easier for travellers to bring their furry companions along. Additionally, rentals typically provide coffee and tea makers for a warm beverage at any time, as well as onsite parking for convenience.
When is the best time to visit Islesboro for a holiday rental?
The best time to visit Islesboro for a holiday rental is during the peak season from June to August, with July being the most popular month. This lively period attracts families and outdoor enthusiasts looking to enjoy the stunning coastal scenery and warm weather. Visitors can indulge in activities like kayaking, sailing, and hiking, all while soaking up the sun on beautiful beaches.During these summer months, temperatures typically range from 15 to 25 degrees Celsius, creating ideal conditions for outdoor exploration and seaside relaxation. The vibrant setting of Islesboro during this time is complemented by community events and local markets, offering a taste of the unique culture the island has to offer.For those seeking a quieter experience and more budget-friendly options, consider visiting in November. This off-peak month presents a serene landscape, superb for peaceful walks along the shore and enjoying the tranquillity of the island without the crowds. The crisp autumn air can be invigorating, making it a lovely time to reflect and recharge.
What are the top attractions in Islesboro?
In Islesboro, Maine, visitors can enjoy a tranquil escape with a variety of attractions that highlight the island's natural beauty and rich history. The island is known for its stunning coastal views and serene beaches, making places like Dark Harbor and the sandy shores at the north end popular spots for relaxation and swimming.The Islesboro Historical Society provides insights into the island's past, showcasing exhibits that reflect the local culture and heritage. For those who appreciate nature, the scenic trails at the Islesboro Island Trust offer opportunities for hiking and exploring the island's diverse ecosystems.Additionally, the picturesque views from the Islesboro ferry terminal are a treat for photography enthusiasts.
Are all fees included in the Islesboro holiday homes prices shown on Bookabach?
Bookabach 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 Islesboro holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Islesboro 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 Islesboro holiday homes?
You can find great discounts on holiday homes in Islesboro on Bookabach, 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 Islesboro holiday home booking on Bookabach?
To find Islesboro holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Islesboro?
A long-stay holiday home in Islesboro 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 Bookabach?
Bookabach'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 Islesboro holiday home?
Book your Islesboro 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Islesboro?
Prices for holiday homes in Islesboro 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. Bookabach offers something for every taste and budget, from affordable homes in Islesboro to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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