Chebeague Island holiday lettings

We found 731 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Chebeague Island that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as a fireplace and garden. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Chebeague Island

Showing deals for:6 Mar - 13 Mar

Image gallery for Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Our private neighborhood path to the beach, lined with beach roses!
10 out of 10, Exceptional, (60 reviews)
Exceptional
(60 reviews)

Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Scarborough, ME

19% off
Price is £3,846
for 7 nights, 1 home
£549 per night
includes taxes & fees
Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Find spaces that suit your style

Explore the waterfront setting in Chebeague Island

Enjoy the history and other features of Chebeague Island. Renowned for its shopping, island views and cycling, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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

Do you want to find things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Chebeague Island a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Nonesuch River Golf Club (15.2 mi / 24.5 km)
  • Ash Cove Pottery (4.8 mi / 7.7 km)
  • Gilsland Farm Audubon Center (7.1 mi / 11.4 km)

Exploring the natural features in Chebeague Island

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chebeague Island is a great place to spend some time outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Casco Bay (6.5 mi / 10.4 km)
  • Sand Beach (7.5 mi / 12 km)
  • East End Beach (8.3 mi / 13.4 km)
  • Desert of Maine (8.5 mi / 13.7 km)
  • Willard Beach (9 mi / 14.5 km)
  • Thompson's Point (11.2 mi / 18 km)

Transport options to and around Chebeague Island

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 12.1 mi (19.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to 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 when booking a holiday rental?
When considering a holiday rental on Chebeague Island, the best area to stay in is the vicinity of Chebeague Island Village. This charming neighbourhood is not only picturesque but also conveniently located near some of the island's top attractions. The village offers a delightful mix of local shops, eateries, and community activities, making it a vibrant hub for visitors.

One of the highlights of staying in this area is the proximity to the Chebeague Island Historical Society, where you can immerse yourself in the island's rich maritime history. Additionally, the nearby Chebeague Island Golf Club provides a lovely spot for those who enjoy a round of golf amidst stunning views of the ocean.
How much does it cost to rent a holiday home in Chebeague Island?
Prices for holiday 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 holiday 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, Maine, consider the picturesque areas along the island's coastline, particularly around the Chebeague Island Yacht Club and the nearby sandy shores. This region offers a variety of holiday rentals with stunning views of Casco Bay, many of which come with amenities such as private decks, outdoor seating, and fully equipped kitchens, making them superb for families or friends looking to enjoy a seaside retreat.

The area near the Chebeague Island Inn provides additional options, where you can find charming cottages that often feature rustic interiors, modern conveniences, and easy access to the beach. Many of these properties include outdoor fire pits and picnic areas, ideal for soaking in the beautiful surroundings after a day of swimming or sunbathing.
What is the most popular type of holiday rental accomodation in Chebeague Island?
On Chebeague Island, holiday houses and cottages are the most popular types of rental accommodations, with several options available. These properties typically feature welcoming interiors, fully equipped kitchens, and comfortable living spaces, making them great for families or groups looking to enjoy a relaxing getaway. Many of the rentals are located near the island's beaches and scenic spots, allowing guests to easily access the stunning coastal views and outdoor activities.
Are there any family house rentals in Chebeague Island?
On Chebeague Island, visitors will find several family-friendly holiday rentals that cater well to groups looking for a memorable getaway. The island's charming neighbourhoods offer a variety of homes equipped with spacious living areas, kitchens for preparing family meals, and outdoor spaces great for children to play and explore. Many properties also boast amenities such as Wi-Fi and comfortable furnishings, ensuring a pleasant stay.
Can I rent a holiday home with a pool or hot tub in Chebeague Island?
In Chebeague Island, there are several holiday homes available for rent that feature pools or hot tubs, making it a delightful choice for travellers seeking relaxation. This charming island offers a serene atmosphere with stunning coastal views, and many of the rentals are situated near the waterfront, providing easy access to sandy beaches and scenic walks.
Can I find long-stay holiday rentals in Chebeague Island?
A long-stay holiday rental in Chebeague 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 Chebeague Island?
In Chebeague Island, there are several pet-friendly house rentals available, making it an excellent destination for travellers who wish to bring their furry companions along. Many of these holiday homes feature spacious interiors, private gardens, and amenities that cater to both pets and their owners, such as outdoor decks and fully equipped kitchens for convenient meal preparation.
Are there any remote work holiday rentals in Chebeague Island?
Chebeague Island, Maine, offers several remote work-friendly holiday rentals, making it an excellent choice for those looking to blend work and leisure. The island features a variety of properties, including charming cottages and spacious homes, many of which are equipped with reliable Wi-Fi and dedicated workspaces to ensure productivity during your stay.

Visitors can enjoy the serene coastal environment, with picturesque views of Casco Bay and easy access to local beaches and walking trails. Amenities in these rentals often include fully equipped kitchens for home cooking, comfortable living areas, and outdoor spaces for relaxation after a day's work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chebeague Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chebeague 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 Chebeague Island?
In Chebeague Island, popular rental amenities include microwaves, patios, and coffee makers in the rooms, making for a comfortable and convenient stay. Many properties also offer cookware, dishware, and utensils, allowing guests to prepare their own meals easily. Additionally, some rentals provide onsite golf facilities, appealing to those looking to enjoy a round in the scenic surroundings.
When is the best time to visit Chebeague Island for a holiday rental?
The best time to visit Chebeague Island for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts visitors eager to embrace the island's charming coastal lifestyle, enjoy outdoor activities, and immerse themselves in the local community events. Warm temperatures, typically in the high teens to low twenties Celsius, create an inviting backdrop for exploring the island's stunning beaches and scenic walking trails.

During these summer months, Chebeague Island comes alive with a variety of recreational opportunities such as kayaking, sailing, and biking. The island's picturesque landscapes, coupled with its quaint shops and delightful eateries, make it a superb destination for travellers.

For those looking for a more budget-friendly option, consider planning your getaway in November. This quieter month allows for a relaxed exploration of the island's natural beauty, with fewer crowds and a chance to enjoy the tranquillity of the off-season. The peaceful atmosphere in late autumn can be quite enchanting, offering stunning coastal views and the chance to connect with nature in a more intimate setting.
How early should I book a Chebeague Island holiday rental?
Book your Chebeague Island holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Chebeague Island home rental booking on Vrbo?
To find Chebeague Island holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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