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-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday 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 holiday home and check out everything that makes Bailey Island a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 traveller 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 centre:

  • 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)
How to get there

Transport 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 centre. 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 near Bailey Island?

Our 2019 accommodation listings offer a large selection of 147 holiday rentals near Bailey Island. From 95 Houses to 45 Cottages, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Bailey Island for a long holiday or a weekend break 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 rentals for a long holiday or just a weekend break in Bailey Island:

  • Topsham: 191 holiday homes
  • Cash Corner: 20 holiday homes
  • Orr's Island: 198 holiday homes
  • Freeport: 16 holiday homes
  • Highlands: 37 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes 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 homes near great places in Bailey Island. From HomeAway travellers, the most popular points of interest to stay near are:

  • Bailey Island Bridge: 934 holiday rentals
  • Spring Point Ledge Lighthouse: 1,314 holiday rentals
  • South Portland Historical Society Museum: 1,344 holiday rentals
  • Brunswick Maine Street Station: 835 holiday rentals
  • Higgins Beach: 1,461 holiday rentals

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 95 Houses in Bailey Island. Our other popular types of Bailey Island holiday rentals include:

  • Cottages: 45 holiday houses
  • Cabins: 45 holiday houses
  • Bungalows: 45 holiday houses

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.

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