Top Bailey Island Holiday Cottages in 2026
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Featured Cottages in Bailey Island

The Outlet House, Comfortable Cottage

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Ocean Inlet Cottage w/ Deck & Grill!

A quintessential Maine cottage experience, captivating guests of all ages

Thorburn - Experience a classic ME vacation at this beautiful summer cottage

Peaceful Lakefront 3 bedroom Cottage On Quiet Forest Lake

Sea Chaser Cottage - Perfect getaway for those drawn to the sea

Cozy Waterfront Cottage in Harpswell, Maine

Waterfront Cottage w/ Fireplace & Deck - Minutes to Downtown

Beach Plum Cottage - on Popham Beach!

Oceanfront Escape: Deck & Granite Steps to Shore
Immerse yourself in local style in Bailey Island Cottages
If you're the sort of traveller who finds yourself seeking out local architecture wherever you visit, and relish the idea of getting a real feel for the cultural identity of destination as embodied by the local landmarks, then you'll probably love Bailey Island Cottages. That's because local styles and local architecture are what tend to set a cottage apart from the crowd. There's none of the cookie-cutter looks of large-scale hotels to be found in this type of accommodation. It's all about immersing yourself in the styles of the region – something that culture lovers are bound to enjoy. Just be ready to wake up in a place that really fits the bill and channels the Bailey Island vibe.
Getting cosy in Bailey Island Cottages
There are few accommodation types in Bailey Island that will have you feeling quite as cosy as a cottage. Quaint and charming, these little boltholes might be just a bed and a bathroom, snug and compact and nestled in their very own little gardens. Others are larger, suited to families looking for somewhere warm and welcoming. They could pack in kitchen areas and dining rooms, lounges with real fires or cushiony sofas, TVs and outdoor porches for curling up and watching the world go by.
A stay in a holiday cottage also brings the added comfort of seclusion. Whether you're a pair of honeymooners in search of somewhere a little more private than a sprawling holiday resort, or a family who need just a tad extra space to spread out, you can rest assured that you'll get it by opting for a cottage from ebookers.
Save money on Bailey Island Cottages
Bailey Island Cottages don't have to break the bank. Far from it. These cosy little nooks could actually help you save money on that next adventure. For starters, they tend to be smaller and more compact than large-scale pads, making them an affordable alternative to other popular family accommodations. What's more, many come with on-site kitchen areas. That means you can rustle up your own food whenever you want, using tasty produce from local markets and drinking wines from local farms. That all saves plenty, especially if you're skipping restaurant trips for the whole family.
Search ebookers to choose the best Bailey Island Cottages
With such a wide range of Bailey Island Cottages on offer on ebookers, you might think it would be tricky to home in on the one that's perfect for you. That's where our accommodation search and travel map come in. They let you filter out all other hotel types and discard cottages that don't have the facilities you're after. And you'll be able to zoom in and out of the destination to discover that hidden holiday cottage you've been pining for. All you need to do is enter the dates you're planning on travelling and ebookers will do the rest.
Bailey Island Cottages essential information
Accommodation | 187 Cottages |
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Popular accommodation | The Outlet House, Comfortable Cottage, Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More, Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage, Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace, Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches, Ocean Inlet Cottage w/ Deck & Grill!, A quintessential Maine cottage experience, captivating guests of all ages, Thorburn - Experience a classic ME vacation at this beautiful summer cottage, Peaceful Lakefront 3 bedroom Cottage On Quiet Forest Lake , Sea Chaser Cottage - Perfect getaway for those drawn to the sea, Cozy Waterfront Cottage in Harpswell, Maine, Waterfront Cottage w/ Fireplace & Deck - Minutes to Downtown, Beach Plum Cottage - on Popham Beach!, Oceanfront Escape: Deck & Granite Steps to Shore, Charming Southport Island Cottage on Cozy Harbor with Sunny Deck - Sleeps 6! |

