Bailey Island Vacation Homes
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Featured Vacation Homes in Bailey Island

Centerview cottage

Beautiful Oceanfront House- Stunning Water Views

Boothbay Harbor Woodland Retreat

5 Star Back Cove Apartment with water view!

Downtown Waterfront Cottage with shoreline sitting room

Rare West End Home • Walk to Old Port, Harbor View

Captain's Guest Room. The authenticity & value in one place. Walk to everything!
Hotel Options in Bailey Island

Clarion Hotel Portland Airport ME

Portland Harbor Hotel

Cambria Hotel Portland Downtown-Old Port
Bailey Island Vacation Homes
Book vacation homes in Bailey Island
Next time you take a group getaway top Bailey Island, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Bailey Island vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.
Homes for every Bailey Island vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Bailey Island; instead of going to a small hotel room at the end of a busy day, you’re going home.
Vacations are all about creating lasting memories, and a Bailey Island rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Bailey Island is sure to be a winner.
Bailey Island Vacation Homes essential information
Accommodation | 576 Vacation Homes |
|---|---|
Lowest Price | $131 |
Highest Price | $862 |
Popular accommodation | Centerview cottage, Beautiful Oceanfront House- Stunning Water Views, Boothbay Harbor Woodland Retreat, 5 Star Back Cove Apartment with water view!, Downtown Waterfront Cottage with shoreline sitting room, Rare West End Home • Walk to Old Port, Harbor View, Captain's Guest Room. The authenticity & value in one place. Walk to everything!, Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need ", Boothbay Harbor, 2-Story Cottage, downtown |


