Chebeague Island vacation rentals

We found 765 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Chebeague Island that are perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as a hot tub and a washer and dryer. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about Chebeague Island

Why visit Chebeague Island

  • Scenic Beaches: Enjoy stunning beaches that provide a perfect backdrop for relaxation and outdoor activities.
  • Outdoor Adventures: Engage in various recreational activities at the Chebeague Recreation Center and explore the island’s natural beauty.
  • Rich Local Culture: Immerse yourself in the island's history and community, enhancing your vacation experience.
  • Charming Accommodations: Choose from a range of vacation rentals, including cozy cottages and stylish condos.
  • Tranquil Atmosphere: Experience the serene, laid-back vibe ideal for romantic getaways or family vacations.

Popular types of accommodation in Chebeague Island

Planning a getaway to Chebeague Island? You’re in the right place. Our most popular vacation rentals include Houses, cozy Cottages, and stylish Condos. Whether you’re looking for Chebeague Island rentals or specific listings like the Chebeague Inn, we have a variety of options to suit your needs. Explore our Maine cottage rentals for a perfect retreat and enjoy the island's charm.

  • Houses: The top choice for visitors to Chebeague Island, offering spacious and comfortable accommodations ideal for families and groups.
  • Cottages: A charming option that provides a cozy, home-like atmosphere, perfect for a relaxing getaway.
  • Condos: A popular selection that combines convenience and great amenities, suitable for a modern vacation experience.
  • Apartments: These offer an affordable and flexible option for travelers seeking a home base during their stay.
  • Cabins: A delightful retreat for those looking to immerse themselves in nature with rustic charm.**

Top attractions near Chebeague Island

Chebeague Island, Maine, is perfect for outdoor and romantic getaways, offering stunning beaches and scenic views. Visitors can explore the charming island, enjoy activities at the Chebeague Recreation Center, and relax at various beach spots. Don't miss out on the local culture and the best vacation rentals available. Whether you're traveling solo or with loved ones, Chebeague Island has something for everyone seeking a memorable coastal experience.

  • Casco Bay: A picturesque bay located 6 miles from Chebeague Island, offering stunning outdoor scenery and beautiful beaches perfect for relaxation and exploration.
  • Little John Island Preserve: Just 2 miles away, this serene preserve features walking trails and friendly locals, providing a peaceful escape with an urban vibe.
  • East End Beach: Situated 8 miles from Chebeague Island, this lovely beach is ideal for sunbathing and enjoying the refreshing ocean breezes.

Things to do recommended for couples

For a romantic getaway on Chebeague Island, consider paddleboarding with Paddleworks for an adventurous day on the water, indulging in luxury at the Portland Club, or enjoying live music at Port City Music Hall. Each offers a unique experience for couples looking to connect and unwind.

Things to do recommended for families

Your family vacation to Chebeague Island promises fun with visits to the Portland Observatory for stunning views, relaxation at Fort Williams Park, and exciting games at Bayside Bowl. Each spot offers unique experiences perfect for family bonding and enjoyment.

Things to do recommended for groups

Groups visiting Chebeague Island can shop at the LL Bean Flagship Store and the Maine Mall, both offering unique experiences. For adventure, the Desert of Maine campground provides outdoor activities perfect for families and friends looking to bond in nature.

*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 Chebeague Island

If you’re traveling with a group, your family, or pets, or if you're considering longer stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chebeague Island with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Chebeague Island with young kids: Traveling with little ones can be quite a challenge. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you may want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chebeague Island: For many families, a vacation wouldn’t be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer essentials like feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chebeague Island: If you're in search of vacation rentals that offer 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 spacious kitchen, or a private pool in your search as well.

Where to stay near Chebeague Island

Chebeague Island, Maine, offers a charming blend of outdoor adventures and scenic beauty, making it an ideal destination for a romantic getaway or a family-friendly vacation. Explore the island’s relaxing beaches, immerse yourself in its rich history, and enjoy the tranquil atmosphere. Nearby neighborhoods provide a unique mix of culture and secluded excursions, ensuring a memorable Maine island experience filled with beach vibes and beautiful properties in a great location.

  • Portland: Located 9 miles from Chebeague Island, Portland is a vibrant coastal city known for its stunning scenery and outdoor activities. Visitors can enjoy the bustling arts scene, with numerous theaters and performance venues showcasing everything from live music to dramatic plays. The city's waterfront offers beautiful beaches and lakes, perfect for a family day out or a relaxing afternoon. Portland’s shopping centers provide an array of local boutiques and well-known brands, making it a great spot for retail therapy. Don’t forget to explore the local culinary scene, famous for its seafood and craft breweries.
  • Casco Bay Islands: Just 2 miles from Chebeague Island, the Casco Bay Islands are an enchanting archipelago that boasts breathtaking natural beauty and outdoor experiences. This area is perfect for beach lovers and those seeking scenic views, with numerous opportunities for hiking, kayaking, and enjoying the great outdoors. Visitors can engage in activities like golfing or exploring educational exhibits at local institutions. With beautiful bays, serene lakes, and pristine beaches, the Casco Bay Islands offer a peaceful retreat from the hustle and bustle.
  • Littlejohn Island: Situated 2 miles from Chebeague Island, Littlejohn Island is a charming destination perfect for eco-friendly travelers and families. The island features a nature reserve and serene parks, ideal for picnics, hiking, and observing local wildlife. One of its highlights is the historic lighthouse, which provides a glimpse into the maritime heritage of the area. Littlejohn Island offers a tranquil escape with its lush landscapes and family-friendly activities, making it a wonderful addition to your vacation itinerary.

Best time to go to Chebeague Island

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.4°F (-3.1°C)Light RainMostly SunnyLowSlightly Low
February27.1°F (-2.7°C)Light RainMostly CloudyAverageSlightly Low
March33.6°F (0.9°C)Light RainMostly SunnyAverageSlightly 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 SunnyLowAverage
December33.1°F (0.6°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily manage your travel plans. You can now find the properties you've saved or booked categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Chebeague Island

Enjoy the history and other features of Chebeague Island. Renowned for its shopping, island views and biking, this city welcomes all visitors. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Chebeague Island

Are you hoping to discover top things to see and do in the area? Venture out of your cozy vacation rental and check out everything that Chebeague Island has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ash Cove Pottery (4.8 mi / 7.7 km)
  • Land's End Gift Shop (5.5 mi / 8.9 km)
  • Paddleworks (6.6 mi / 10.6 km)
  • Happy Wheels Skate Center (11.9 mi / 19.2 km)
  • Spring Meadows Golf Course (15.5 mi / 24.9 km)
  • Gilsland Farm Audubon Center (7.1 mi / 11.4 km)

Exploring the natural features in Chebeague Island

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Chebeague Island is a great spot to appreciate mother nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Casco Bay (6.5 mi / 10.4 km)
  • Sand Beach (7.5 mi / 12 km)
  • East End Beach (8.3 mi / 13.4 km)
  • Eastern Promenade (8.4 mi / 13.5 km)
  • Desert of Maine (8.5 mi / 13.7 km)
  • Willard Beach (9 mi / 14.5 km)

Transportation options to and around Chebeague Island

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 12.1 mi (19.4 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 23 mi (37.1 km) away.

Frequently asked questions

What is the best area to stay in Chebeague Island, Maine, United States of America when booking a vacation rental?
When considering a vacation rental in Chebeague Island, Maine, the best area to stay is often near the waterfront. This picturesque part of the island offers stunning views of Casco Bay and easy access to various outdoor activities. You'll find a charming selection of vacation homes and cottages that allow you to soak in the island's serene atmosphere.

One of the top attractions in this area is the Chebeague Island Historical Society, where visitors can learn about the island's rich maritime history. Additionally, the nearby Chebeague Island Golf Club is a delightful spot for those looking to enjoy a round of golf while surrounded by breathtaking landscapes. The waterfront area also provides convenient access to local eateries, where you can savor fresh seafood and enjoy the island's laid-back vibe.
How much does it cost to rent a vacation home in Chebeague Island?
Prices for vacation rentals in Chebeague 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chebeague Island 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 Chebeague Island vacation house rentals?
You can find great discounts on house rentals in Chebeague 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 Chebeague Island?
For renting a beach house in Chebeague Island, travelers should explore the picturesque waterfront areas, particularly around the Chebeague Island Marina and the nearby beaches. This region boasts charming vacation rentals that often feature stunning views of Casco Bay, spacious decks for outdoor dining, and easy access to sandy shores. Many properties come equipped with amenities like kayaks, outdoor grills, and well-appointed kitchens, making them great for families and groups seeking a relaxing seaside getaway.

The area around the Chebeague Island Inn offers additional options, where visitors can find lovely cottages and homes that provide a blend of modern comforts and coastal charm. These rentals typically include cozy living spaces, private gardens, and proximity to local attractions such as the island's historic lighthouse and nature trails. Guests can enjoy leisurely strolls along the shoreline or partake in various activities like fishing and boating.

Furthermore, the island's close-knit community vibe and local eateries add to the experience, allowing travelers to immerse themselves in the laid-back island lifestyle.
What is the most popular type of vacation rental accomodation in Chebeague Island?
In Chebeague Island, vacation houses and cottages are the most popular types of rentals, with several options available throughout the island. These properties typically offer a charming, rustic atmosphere, great for enjoying the coastal beauty of Maine. Most vacation houses and cottages come equipped with essential amenities such as fully stocked kitchens, comfortable living spaces, and outdoor decks or porches for taking in the stunning views of Casco Bay.
Are there any family house rentals in Chebeague Island?
In Chebeague Island, Maine, there are several family-friendly house rentals available, making it a lovely spot for families looking to enjoy a coastal getaway. The island features charming neighborhoods with homes that often include spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play and explore. Many properties come equipped with amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay for all.

Visitors can take advantage of nearby attractions such as local beaches great for swimming and picnicking, as well as scenic walking trails that showcase the island's natural beauty. The proximity to the Chebeague Island Historical Society offers a glimpse into the local culture and history, providing an enriching experience for families.
Can I rent a vacation home with a pool or hot tub in Chebeague Island?
In Chebeague Island, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque island offers a serene escape with beautiful coastal views and a charming community atmosphere. Many of these properties come equipped with desirable amenities such as private pools, hot tubs, outdoor patios, and fully equipped kitchens, making them great for relaxation and family gatherings. Travelers can also enjoy nearby activities such as hiking and exploring the island's unique landscapes, enhancing their overall vacation experience.
Can I find long-stay vacation rentals in Chebeague Island?
A long-stay vacation rental in Chebeague Island 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 Chebeague Island?
In Chebeague Island, there are several pet-friendly house rentals available, making it an excellent destination for travelers looking to enjoy a coastal getaway with their furry companions. Many of these vacation homes feature welcoming amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios where pets can enjoy the fresh sea air. The island's picturesque surroundings and relaxed atmosphere provide a superb backdrop for a memorable vacation.

While exploring the area, pet owners will appreciate the proximity to various outdoor spaces, including beaches and walking trails, where they can take their pets for strolls.
Are there any remote work vacation rentals in Chebeague Island?
In Chebeague Island, Maine, there are several vacation rentals suitable for remote work. Many properties offer essential amenities like Wi-Fi and internet access, ensuring that guests can stay connected while enjoying the serene island atmosphere. Travelers can expect comfortable accommodations with features such as dedicated workspace areas, cozy living rooms, and fully equipped kitchens, making it easy to balance work and leisure.

The island itself is known for its beautiful coastal views, charming landscapes, and outdoor activities like hiking and biking, providing a great backdrop for those looking to combine work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chebeague Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chebeague Island 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 Chebeague Island?
In Chebeague Island, popular rental amenities cater to families and those seeking a comfortable getaway. Many properties feature kitchens, allowing guests to prepare their own meals, while decks or patios provide outdoor spaces for relaxing and enjoying the scenic views. Some rentals also include porches or lanais, superb for taking in the island's serene atmosphere. Additionally, several accommodations offer books for children, making them ideal for families traveling with kids.
When is the best time to visit Chebeague Island for a vacation rental?
The best time to visit Chebeague Island for a vacation rental is during the peak summer months of June to August, with July being the most popular month among travelers. This vibrant season attracts those seeking a quintessential Maine experience, where the warm weather and sunny days create a friendly space for outdoor activities such as kayaking, sailing, and exploring the island's scenic trails.

During these months, visitors can enjoy temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, providing comfortable conditions for beach outings and leisurely strolls along the shore. The island's charming local shops and dining options thrive, offering fresh seafood and delightful treats that enhance the vacation experience.

For those looking to travel on a budget, consider visiting in November, when the island is quieter and offers a unique sense of tranquility. While the temperatures dip to the low 30s and 40s Fahrenheit, this time of year is great for those who appreciate the peacefulness of the off-season, where you can enjoy coastal walks and take in the stunning fall scenery without the hustle and bustle of peak tourist crowds.

Ultimately, your ideal time to visit Chebeague Island hinges on whether you want to immerse yourself in the lively summer atmosphere or seek a more serene experience in the late fall.
How early should I book a Chebeague Island vacation rental?
Book your Chebeague 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.
What are the top attractions in Chebeague Island, Maine, United States of America?
On Chebeague Island, visitors can explore a variety of attractions that highlight the island's natural beauty and charm. The Chebeague Island Historical Society offers insights into local history and culture, making it a great stop for those interested in the island's heritage. The island is known for its picturesque beaches, such as the lovely Chandler's Cove, where visitors can enjoy swimming, sunbathing, and stunning views of Casco Bay.

Outdoor enthusiasts can explore the numerous walking trails that wind through the island, providing opportunities for hiking and birdwatching. The island's community parks, such as the Chebeague Island Recreation Center, often host events and activities, offering a glimpse into the local way of life.

Additionally, the nearby Chebeague Island Golf Club presents a great experience for golf lovers, with beautiful views and a relaxed atmosphere.
Can I change or cancel my Chebeague Island home rental booking on Vrbo?
To find Chebeague 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 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 Chebeague 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.
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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