Bailey Island Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Bailey Island

Captain's House 2BR Apartment. Walk to Everything!

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Oceanfront Cabin-Castle in Maine Woods

Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

The Cityside Maple House

Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Camp Forever cottage

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Holiday Accommodation Bailey Island
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Bailey Island are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Bailey Island itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Bailey Island holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Bailey Island, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Bailey Island with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Bailey Island Holiday Homes essential information
Accommodation | 581 Holiday Homes |
---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Captain's House 2BR Apartment. Walk to Everything!, Charming 2-bedroom house with AC, WiFi in lovely Falmouth, Oceanfront Cabin-Castle in Maine Woods, Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer, The Cityside Maple House, Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access, Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces, New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach, Camp Forever cottage, Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, Downtown Boothbay Harbor, 2-Story Cottage, Rent a room in the gorgeous Holt House |
More accommodations in Bailey Island
Top trending hotels in Bailey Island

BAILEY ISLAND MOTEL
^Eligibility requirements and conditions apply