Destination guide

Take in the waterfront beauty of Chebeague Island

Enjoy the history and other features of Chebeague Island. This city's shopping, island views and cycling draw many visitors. Portland Observatory and Wadsworth-Longfellow House are just a couple of the must-see attractions in the area. 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.


Activities and attractions in Chebeague Island

Are you hoping to find top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Chebeague Island a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Wilbur's of Maine Chocolate Confections (7.7 mi / 12.4 km)
  • Southworth Planetarium (9.6 mi / 15.4 km)
  • Riverside Municipal Golf Course (9.9 mi / 16 km)
  • Joker's Family Fun and Games (10.8 mi / 17.5 km)
  • Sable Oaks Golf Course (13.1 mi / 21.1 km)
  • Twin Falls Golf Club (13.2 mi / 21.2 km)
Natural features

Exploring the natural landscape of Chebeague Island

Whether you're an adventurous traveller or just want to appreciate the scenery, Chebeague Island is a great place to get out in nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Casco Bay Islands (1.1 mi / 1.7 km)
  • Eagle Island State Park (3.5 mi / 5.7 km)
  • Wolfe's Neck State Park (6.4 mi / 10.4 km)
  • Casco Bay (6.6 mi / 10.6 km)
  • Mackworth Island (6.7 mi / 10.7 km)
  • Wolfe's Neck Farm (6.8 mi / 11 km)
How to get there

Transport options to and around Chebeague Island

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 11.5 mi (18.6 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Brunswick, ME (NHZ-Brunswick Executive), which is 14.2 mi (22.9 km) away.

How many holiday rentals are available around Chebeague Island?

Our 2019 accommodation listings offer a large selection of 543 holiday lettings around Chebeague Island. From 264 Houses to 114 Cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What is the best area to stay when travelling to Chebeague Island?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chebeague Island:

  • Orr's Island: 200 holiday homes
  • Willard: 31 holiday homes
  • West Point: 17 holiday homes
  • Pine Point: 279 holiday homes
  • Town Landing: 21 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Chebeague Island?

HomeAway offers a large selection of holiday accommodations near great places in Chebeague Island. From HomeAway travellers, the most popular points of interest to stay near are:

  • Scarborough Downs: 1,424 holiday lettings
  • Scarborough Beach State Park: 1,356 holiday lettings
  • Southern Maine Community College: 1,328 holiday lettings
  • Dunegrass Golf Club: 1,583 holiday lettings
  • Southworth Planetarium: 1,392 holiday lettings

But there are many other points of interest around Chebeague Island listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Chebeague Island?

Yes, of course. HomeAway offers 264 Houses in Chebeague Island. Our other popular types of Chebeague Island holiday rentals include:

  • Cottages: 114 self catering accommodations
  • Cabins: 114 self catering accommodations
  • Bungalows: 114 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Flats and more.

Can I find a holiday accommodation with pool in Chebeague Island?

Yes, you can select your preferred holiday accommodation with pool among our 18 holiday homes with pool available in Chebeague Island. Please use our search bar to access the selection of holiday rentals available.

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