Harpswell vacation rentals

We found 493 vacation rentals — enter your dates for availability

Select from 90 homes, 43 cottages, and other vacation rentals in Harpswell to find one that's perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as parking and air conditioning. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Harpswell

Why visit Harpswell

  • Stunning Beaches: Harpswell boasts beautiful beaches perfect for sunbathing, swimming, and beachcombing.
  • Charming Harpswell Islands: Explore the serene harbors and picturesque landscapes of the Harpswell Islands area.
  • Outdoor Adventures: Enjoy a variety of outdoor activities such as hiking, kayaking, and wildlife watching.
  • Historic Sites: Discover local history through charming historic houses and landmarks throughout the region.
  • Relaxing Atmosphere: Experience the friendly locals and peaceful environment ideal for a romantic getaway or family vacation.

Popular types of accommodation in Harpswell

Planning a getaway to Harpswell? You're in for a treat. Discover the charm of this coastal destination with a variety of vacation rentals to suit your needs. From cozy cottages and houses to modern apartments, you'll find the perfect spot to relax. Explore your options for house rentals and cottage rentals, ensuring a memorable stay in this picturesque Maine locale. Start your adventure with the ideal Harpswell vacation rental today.

  • Houses: The top choice for visitors to Harpswell, these spacious homes offer all the comforts of a home away from home, perfect for families and groups.
  • Cottages: These quaint and cozy retreats provide a charming escape, ideal for a romantic getaway or peaceful solo retreat.
  • Apartments: A convenient option for those looking for a home base, these rentals are perfect for couples or solo travelers.
  • Condos: Offering modern amenities and often stunning views, condos are a popular choice for those seeking comfort and luxury.
  • Cabins: Nestled in nature, these rustic lodgings offer a serene environment, perfect for outdoor enthusiasts.**

Top attractions near Harpswell

Harpswell, Maine, offers a perfect blend of outdoor adventures and romantic scenery, making it an ideal vacation spot. Visitors can explore stunning beaches, national parks, and historic houses, immersing themselves in the local culture and natural beauty. Whether you're seeking a relaxing getaway or exciting activities, Harpswell has something for everyone, ensuring a memorable experience for solo travelers, couples, and families alike.

  • Bowdoin College: This historic college offers a rich cultural experience with stunning architecture, beautiful campus landscapes, and a vibrant arts scene. Explore its museums and galleries, and enjoy the college's commitment to liberal arts education.
  • Popham Beach: A picturesque beach perfect for sunbathing, swimming, and beachcombing. With its sandy shores and scenic views, it's an ideal spot for relaxation and enjoying coastal Maine's natural beauty.
  • Maine Street: Experience the lively atmosphere of this charming street filled with local shops, cafes, and restaurants. Maine Street is perfect for a leisurely stroll while soaking in the local culture and community vibe.

Things to do recommended for couples

For a romantic getaway in Harpswell, consider paddling together at Paddleworks, just 5 miles away, where adventure awaits. Alternatively, enjoy some friendly competition at Dolphin Mini Golf, 16 miles away, perfect for a fun-filled day with family vibes.

Things to do recommended for families

Families will love visiting Wilbur's of Maine Chocolate Confections for sweet treats, exploring the Twin Brook Recreation Area for wellness and relaxation, and experiencing the Portland Observatory for family entertainment. Each destination offers a unique vibe just a short drive from Harpswell.

Things to do recommended for groups

In Harpswell, groups can shop at the LL Bean Flagship Store, enjoy a captivating performance at the Maine State Music Theater, and experience adventure at the Desert of Maine campground. Each location offers unique vibes, making it perfect for a memorable group vacation.

*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 Harpswell

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to filter your options based on what matters most to you. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Harpswell with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Harpswell with young kids: Traveling with little ones can be a bit tough. It's important to prioritize their comfort and safety, along with having access to kid-friendly amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Harpswell: For many families, a vacation wouldn't be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Harpswell: If you're searching for vacation rentals with discounts 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 criteria as well.

Where to stay in Harpswell

Harpswell, Maine, offers a delightful blend of outdoor adventures and scenic beauty, making it ideal for a romantic getaway or a relaxing family vacation. Explore the charming Harpswell Islands area, where tranquil harbors and picturesque landscapes await. Enjoy friendly locals and a peaceful atmosphere as you discover this coastal gem, perfect for recreation and relaxation. Don't miss the chance to experience the enchanting surroundings that make Harpswell a unique destination on the Outer Banks of Maine.

  • Sebascodegan Island: Nestled in the heart of Harpswell, Sebascodegan Island is a picturesque village known for its stunning outdoor scenery and tranquil beaches. Visitors flock to this serene island for a true escape into nature, enjoying activities such as hiking along scenic trails and relaxing at family-friendly beaches. The local recreational areas offer ample opportunities for exploration, while the nearby lake enhances the picturesque landscape. The island's charm lies in its unspoiled beauty, making it an idyllic spot for those seeking a peaceful retreat.
  • Harpswell Center: As the vibrant hub of Harpswell, Harpswell Center encapsulates the essence of Maine's outdoor charm. This enchanting village is perfect for romantic getaways, featuring scenic views and inviting recreational areas. Visitors can enjoy various activities, including skiing at local fields or catching a show at the arena entertainment facility. The surrounding landscape is dotted with beautiful lakes and beaches, providing endless opportunities for relaxation and adventure. Harpswell Center serves as an excellent base for exploring the stunning coastal region.
  • West Harpswell: West Harpswell offers a delightful blend of outdoor activities and picturesque scenery, making it an appealing neighborhood for travelers. Known for its romantic atmosphere, this area boasts numerous recreational spots and a local theater that showcases community performances. Nature enthusiasts will appreciate the proximity to beautiful lakes, pristine beaches, and the captivating national state park. West Harpswell's enchanting landscape invites visitors to immerse themselves in Maine's natural beauty while enjoying a variety of activities.

Best time to go to Harpswell

If you're planning a trip to Harpswell, 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 November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.3°F (-3.7°C)Light RainMostly SunnyLowSlightly Low
February26.4°F (-3.1°C)Light RainMostly CloudyAverageSlightly Low
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April43.3°F (6.3°C)Light RainMostly CloudyAverageAverage
May53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
June61.2°F (16.2°C)Light RainMostly SunnyHighSlightly High
July68.2°F (20.1°C)Light RainMostly SunnyHighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
September61.7°F (16.5°C)Light RainMostly SunnyAverageAverage
October51.8°F (11.0°C)Light RainMostly SunnyAverageAverage
November40.6°F (4.8°C)Light RainMostly SunnyLowAverage
December32.4°F (0.2°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you aiming to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that aligns with your budget, simply utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. It truly benefits you to take on the planning role. By enrolling in our travel rewards program, OneKey, you’ll gain access to exclusive member discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you plan your travels more effectively. It provides a dedicated space where you can start new trips, refine your existing plans, or review and manage your bookings. All your saved or booked properties are conveniently organized into categories: Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Cool, coastal, collected—rugged and refined in Maine

Nestled amid a cluster of 5 peninsulas on Casco Bay, the quaint and quiet town of Harpswell offers everything you'd expect from a charming New England town. From Orr's Island's rugged, made-for-exploring coastline to a town center whose classic Americana vibe would put Norman Rockwell to shame, you'll be sure to fall in love with this laid-back island town. Consider Harpswell vacation rentals with a view of the bay or seashore access, and get ready to experience a seaside community unlike any other on the New England coast.

Harpswell's art and history—a match made in heaven

Art lover? Then be sure to visit the Sebascodegan Artists Gallery, where you can explore work by a number of regional artists. Other highlights in town include The Elijah Kellogg Church and the nearby Harpswell Town Meeting House, both built in 1757. Afterwards, head to the Historical Society Museum to read all about their role in shaping the town. On nearby Eagle Island, you'd be well advised to take a tour of the summer home of Arctic explorer Admiral Robert E. Peary. From here, you can easily walk the four-mile trail around the island before heading back to Harpswell.

Summers are sure to sparkle in maritime Maine

January through March is the coldest time on Orr's Island, with little to do except relax by the fire. If this sounds like your cup of tea—and trust us, you'll probably need a few—then consider wintertime Harpswell vacation rentals, when crowds are minimal and deals more plentiful. Alternatively, summers see a surge of visitors to the region, making June through August the busier, more expensive season. You'll be rewarded with the best weather of the year, however, and ideal conditions for exploring the great outdoors. Fall can be chilly and wet, but the region's world-famous leaf peeping is always worth the trip.

Go forth! Find your inner explorer in Harpswell

Harpswell and Orr's Island offer a quiet coastal escape from the buzz in nearby Portland. With expansive views of forested islands and a famously jagged, craggy coastline, you'd be forgiven for spending time just basking in the region's scenery. Seagulls can be spotted everywhere, while seafood shanties offer up the local catch of the day—including Maine's not-to-be-missed lobster dishes (or "lobstah," as the locals say). Enjoy the tranquil harbor, hike along the tree lined trails, or hop on a boat and sail out to explore the other islands nearby.

How to get to and around Harpswell

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 20 mi (32.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Wiscasset, ME (ISS), which is 17.4 mi (28 km) away.

Frequently asked questions

What is the best area to stay in Harpswell when booking a vacation rental?
When planning a vacation in Harpswell, Maine, one of the best areas to consider for your rental is Bailey Island. This picturesque neighborhood offers stunning ocean views and a charming coastal atmosphere. Visitors can explore the iconic Cribstone Bridge, an engineering marvel that connects Bailey Island to the mainland, and enjoy the serene beauty of the nearby beaches. With a range of vacation rentals available, you're likely to find a cozy cottage or a waterfront property that suits your needs.

Another excellent option is the area around Great Island. This part of Harpswell is great for those who appreciate nature and outdoor activities. Here, you can enjoy hiking trails with breathtaking views and access to the Great Island Trail, a wonderful spot for both walking and birdwatching.
How much does it cost to rent a vacation home in Harpswell?
Prices for vacation rentals in Harpswell 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Harpswell to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Harpswell vacation house rentals?
You can find great discounts on house rentals in Harpswell 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 Harpswell?
For renting a beach house in Harpswell, Maine, travelers should explore the scenic areas along the coast, particularly around the picturesque Bailey Island and Great Island. The coastline here features stunning views of Casco Bay and offers several vacation rentals that come with direct beach access, spacious decks for outdoor lounging, and fully equipped kitchens, superb for families or groups looking to enjoy a coastal retreat.

In the Bailey Island area, visitors can find charming cottages and waterfront properties that often include amenities such as private docks, outdoor grills, and fire pits, creating an ideal setting for enjoying summer evenings by the water. The nearby Harpswell Heritage Land Trust preserves numerous trails and natural spaces, allowing for easy access to hiking and exploration just a short distance from many rentals.

Additionally, the area around the Cribstone Bridge offers a unique coastal experience, with properties providing views of this iconic structure. Rentals here often feature cozy interiors, multiple bedrooms, and some even have access to kayaks or paddleboards, great for those looking to explore the bay. Find your rental near the beach in Harpswell.
What is the most popular type of vacation rental accomodation in Harpswell?
In Harpswell, vacation houses are the most popular type of rental accommodation, with about 84 available throughout the area. These homes are often situated near the coast, providing stunning views of the waterfront and easy access to local attractions such as the Harpswell Heritage Land Trust trails and the scenic Bailey Island. Most vacation houses come equipped with fully stocked kitchens, spacious living areas, and outdoor decks or patios, superb for enjoying the picturesque surroundings.

Cottages also make up a significant portion of the offerings, with around 44 options available. These cozy retreats typically feature charming interiors, often with rustic decor, and provide amenities like fireplaces and outdoor fire pits, ideal for a relaxing evening after a day of exploring.

Additionally, there are several apartments and cabins available, though they are less common. Apartments typically include essential amenities for a comfortable stay, while cabins often offer a more rustic experience with a focus on nature, sometimes located in wooded areas.
Are there any family house rentals in Harpswell?
In Harpswell, Maine, there are numerous family-friendly house rentals available, with around 117 options scattered throughout the area. This coastal town offers beautiful waterfront views and easy access to outdoor activities, making it an ideal location for families. Many homes feature spacious living areas, fully equipped kitchens for preparing family meals, and comfortable dining spaces for gathering together. Outdoor amenities such as decks or patios allow for relaxation while enjoying the fresh sea air.

Families can explore nearby attractions like the scenic trails of the Harpswell Heritage Land Trust or visit local beaches for swimming and picnicking. Additionally, the charming village of Bailey Island is just a short drive away, where visitors can find quaint shops and seafood restaurants. See all family-friendly rentals in Harpswell.
Can I rent a vacation home with a pool or hot tub in Harpswell?
In Harpswell, Maine, there are several vacation homes available for rent that feature pools and hot tubs, providing travelers with a refreshing and relaxing experience. This picturesque coastal town is known for its stunning waterfront views and charming lighthouses, making it an attractive destination for visitors. Many of the vacation rentals in Harpswell offer amenities such as private pools, hot tubs, outdoor seating areas, and fully equipped kitchens, ideal for families or groups looking to unwind after a day of exploring the beautiful coastline. Find your rental in Harpswell with a pool or a hot tub.
Can I find long-stay vacation rentals in Harpswell?
A long-stay vacation rental in Harpswell is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Harpswell?
In Harpswell, travelers can find a variety of pet-friendly house rentals, with around 66 options available. These vacation homes often come equipped with essential amenities such as fully stocked kitchens, outdoor spaces for relaxation, and cozy living areas, making them suitable for families and groups. Many properties offer stunning views of the surrounding coastline or access to nearby beaches, providing a friendly space for both guests and their furry companions.

The area is known for its picturesque landscapes and charming coastal villages, with easy access to outdoor activities such as hiking, kayaking, and exploring local parks. Pet-friendly points of interest include nearby beaches and trails where pets can enjoy the fresh air and scenic surroundings. See all pet-friendly rentals in Harpswell.
Are there any remote work vacation rentals in Harpswell?
In Harpswell, Maine, there are numerous remote work vacation rentals available, with about 122 options to choose from. This picturesque coastal town is an excellent choice for those looking to combine work and leisure. Many of the properties are equipped with dedicated office spaces, including desks and ergonomic chairs, ensuring a comfortable working environment. High-speed Wi-Fi is typically available, allowing for seamless connectivity during work hours.

Travelers can expect properties that feature amenities such as computer monitors and safes for securing valuables. Additionally, many rentals offer stunning views of the water, along with outdoor spaces where one can relax after a productive day. The charming local area is dotted with scenic points of interest, including lighthouses and walking trails, making it a delightful place to unwind in between work commitments. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Harpswell vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Harpswell with parking available—perfect for families or travelers 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 Harpswell?
In Harpswell, popular vacation rental amenities include WiFi, kitchens, patios, coffee and tea makers, and decks or patios. These amenities enhance the comfort and convenience of stays, allowing travelers to enjoy home-cooked meals and beautiful views while relaxing outdoors. Many rentals are situated near scenic coastal areas, making them great for exploring the stunning natural landscapes of Maine.
When is the best time to visit Harpswell for a vacation rental?
The best time to visit Harpswell for a vacation rental is during the peak season of June to August, with July being the most popular month. This vibrant period attracts travelers eager to soak up the sun and enjoy the stunning coastal scenery, superb for outdoor activities such as kayaking, sailing, and exploring the picturesque shorelines.

During these summer months, temperatures typically range from the mid-60s to mid-80s Fahrenheit, providing ideal conditions for enjoying the outdoors. Visitors can take advantage of the beautiful weather to hike along the scenic trails or enjoy fresh seafood at local eateries while overlooking the ocean.

For those seeking a more budget-friendly experience, November offers a quieter alternative. The fall season brings a unique charm to Harpswell, with fewer crowds and opportunities to enjoy the crisp autumn air while taking leisurely walks along the coast. It's a time to appreciate the natural beauty of the area, with the changing foliage providing a stunning backdrop.

Ultimately, the best time to visit Harpswell will depend on whether you prefer the bustling summer atmosphere filled with activities or the tranquil beauty of the fall season.
How early should I book a Harpswell vacation rental?
Book your Harpswell 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.
What are the top attractions in Harpswell?
In Harpswell, Maine, visitors can enjoy a variety of attractions that highlight the area's natural beauty and maritime heritage. The picturesque coastline offers stunning views, with places like the Harpswell Coastal Trails providing scenic walking paths and access to the water. The trails meander through forests and along the shore, making it an ideal spot for hiking and birdwatching.

Another highlight is the iconic Bailey Island, accessible via the Cribstone Bridge, where travelers can explore charming seaside cottages and enjoy fresh seafood at local eateries. The area is also known for its lighthouses, such as the historic Cape Elizabeth Light, which offers beautiful photo opportunities and is steeped in maritime history.

In addition, the nearby Brunswick area boasts attractions like the Bowdoin College Museum of Art and the Androscoggin River, great for those interested in culture and outdoor activities.
Can I change or cancel my Harpswell home rental booking on Vrbo?
To find Harpswell 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Harpswell 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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