Bailey Island vacation rentals
Find spaces that suit your style
Find the best place to stay - Bailey Island
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Top rated rentals - Bailey Island
Vacation on the ocean
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Take in the waterfront beauty 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. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.
Activities and attractions in Bailey Island
Do you want to find things to do during your stay? Venture out of your cozy vacation rental and check out everything that makes Bailey Island a fun spot to vacation. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:
- Casco Bay Lines Ferry Terminal (13.9 mi / 22.4 km)
- Land's End Gift Shop (1.3 mi / 2.1 km)
- Paddleworks (1.7 mi / 2.8 km)
- Ash Cove Pottery (1.4 mi / 2.3 km)
- Wilbur's of Maine Chocolate Confections (9.7 mi / 15.6 km)
- Capt Lyman Stuart, LLC (10.9 mi / 17.6 km)
Exploring the natural landscape of Bailey Island
Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Bailey Island. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:
- Casco Bay (2.8 mi / 4.6 km)
- Little John Island Preserve (6.8 mi / 11 km)
- Wolfe's Neck Woods State Park (7.5 mi / 12.1 km)
- Popham Beach State Park (9.8 mi / 15.7 km)
- Popham Beach (10.6 mi / 17.1 km)
- Desert of Maine (11.7 mi / 18.8 km)
Transportation to and around Bailey Island
The nearest airport is in Portland Intl. Jetport Airport (PWM), located 17 mi (27.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away.