Destination guide

Delight in the waterfront landscape of Bailey Island

Enjoy the monuments and other features of Bailey Island. Renowned for its island views, shopping and fishing, this city welcomes all visitors. Portland Head Light and Portland Observatory are just a couple of the must-sees in the area. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.


Sightseeing in and around Bailey Island

Are you hoping to find top things to see and do while you're in the area? Venture out of your vacation home and check out everything that makes Bailey Island a fun spot to vacation. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Wilbur's of Maine Chocolate Confections (10.2 mi / 16.5 km)
  • Brunswick Golf Club (13.1 mi / 21 km)
  • Brunswick Golf Course (13.1 mi / 21 km)
  • Southworth Planetarium (15.3 mi / 24.6 km)
  • Riverside Municipal Golf Course (16.3 mi / 26.2 km)
Natural highlights

Exploring the natural landscape of Bailey Island

Whether you're an adventurous traveler or just want to take in the scenery, Bailey Island is a great place to get outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Casco Bay (2.5 mi / 4 km)
  • Eagle Island State Park (3.6 mi / 5.8 km)
  • Casco Bay Islands (6.4 mi / 10.3 km)
  • Hermit Island (6.6 mi / 10.7 km)
  • Bates-Morse Mountain Conservation Area (7.9 mi / 12.7 km)
  • Wolfe's Neck Farm (8.1 mi / 13 km)

Transportation to and around Bailey Island

Fly into Brunswick, ME (NHZ-Brunswick Executive), the closest airport, located 11.5 mi (18.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Portland, ME (PWM-Portland Intl. Jetport), which is 17.2 mi (27.7 km) away.

Where to stay around Bailey Island?

Our 2019 accommodation listings offer a large selection of 149 holiday lettings near Bailey Island. From 97 Houses to 46 Cottages, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Bailey Island is on HomeAway.

What is the best area to stay when travelling to Bailey 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 Bailey Island:

  • Scarborough: 756 holiday homes
  • Peaks Island: 82 holiday homes
  • West End: 62 holiday homes
  • Freeport: 830 holiday homes
  • Yarmouth: 806 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 Bailey Island?

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

  • Bailey Island Bridge: 971 holiday lettings
  • Seguin Island Lighthouse: 894 holiday lettings
  • Higgins Beach: 1,512 holiday lettings
  • Reid State Park: 970 holiday lettings
  • Cape Elizabeth Light: 1,401 holiday lettings

But there are many other points of interest around Bailey 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 Bailey Island?

Yes, of course. HomeAway offers 97 Houses in Bailey Island. Our other popular types of Bailey Island holiday rentals include:

  • Cottages: 46 self catering accommodations
  • Cabins: 46 self catering accommodations
  • Bungalows: 46 self catering accommodations

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

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

Yes, you can select your preferred holiday accommodation with pool among our 4 holiday homes with pool available in Bailey Island. Please use our search bar to access the selection of holiday rentals available.

    Explore destinations around Bailey Island

    756 holiday rentals
    735 holiday rentals
    437 holiday rentals
    777 holiday rentals
    698 holiday rentals
    477 holiday rentals
    Peaks Island
    82 holiday rentals
    565 holiday rentals
    762 holiday rentals
    75 holiday rentals
    1,205 holiday rentals
    New Gloucester
    245 holiday rentals
    830 holiday rentals
    64 holiday rentals
    236 holiday rentals
    607 holiday rentals
    105 holiday rentals
    129 holiday rentals
    20 holiday rentals
    198 holiday rentals