Discover a selection of 131 vacation rentals in Bailey Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and kitchens. Prices start at $116 per night, and cottages and houses are popular options for a stay in Bailey Island. Either way, you'll find a rental for everyone's needs.
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Destination guide

Soak up Bailey Island's alluring old-world vibe

Jutting off Maine's ruggedly beautiful coast into the deep blue Atlantic, Bailey Island lures visitors from far and wide thanks to its pristine shorelines, its sedate way of life and its beguiling old-world ambience. Bailey is located in the town of Harpswell, home to one of Maine's last remaining working harbors, which you'll invariably find packed with gently bobbing fishing boats and yachts. The island is also scattered with quirky boutiques and welcoming inns serving hearty home-cooked fare. Bailey Island vacation rentals range from cozy cottages perfect for a romantic getaway to sprawling family homes where you could host a big family get-together.

Things to do

Bailey Island's natural wonders

As you approach the island, it's certainly worth stopping to marvel at the distinctive Bailey Island Bridge. Constructed in the 1920s, it was recognized in 1984 as a Historic Civil Engineering Landmark, as it was believed to be the only bridge on the planet made of granite cribstone. Once you've settled into your Bailey Island vacation rental, be sure to make a pit-stop at Mackerel Cove, a picture-postcard harbor where the shimmering water is ideal for swimming in the summer, and crabbing when it's cooler outside. For further spectacular coastal scenery, take a short hike to the Giant's Stairs, a dramatic rocky outcrop that dates back over 500 million years, where crashing waves can often be seen in the gleaming sunshine.

Activities

Shopping and seafood feasts on Bailey Island

Discerning shoppers will be enthralled by Bailey Island's array of independent stores, where you can pick up everything from one-of-a-kind artworks to exquisite hand-crafted jewelry to chic designer fashion. Bailey's dining scene is similarly captivating, Freshly-caught seafood naturally features prominently on many menus, so you can look forward to feasting on creamy clam chowder, buttery lobster rolls, decadent deep-fried clams or locally harvested oysters. If you fancy learning how your dinner was caught, join a lobster harvesting tour, where a local expert will talk you through the history of lobster trapping as you head out to sea, before showing you precisely how it's done.

Weather

Vivid seasons on Bailey Island

Bailey Island vacation rentals draw in big numbers of visitors during the sun-dappled months of summer. The days are long, warm and sunny, ideal for afternoons at sea or strolling down coastal paths. Winters, by contrast, are rather cold, with temperatures frequently tumbling below freezing and a fair amount of snowfall. Spring and fall are great times to visit, with mild to warm temperatures and fewer out-of-towners competing for prime accommodation.

Natural features

Animal encounters on Bailey Island

Unspoiled Bailey Island is a haven for nature and wildlife lovers. Its waters serve as a naturally spectacular habitat for playful porpoises, seals and other adorable marine life. Birders are also in for a treat, with rare hooded warblers, majestic osprey and all manner of other species making their home here. And, of course, Bailey Island is a prime fishing destination, its waters teeming with everything from giant tuna to sharks.

How to get there

Transportation 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 center. 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.

How many vacation rentals are available around Bailey Island?

Our 2020 property listings offer a large selection of 131 vacation rentals around Bailey Island. From 57 cottage rentals to 67 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Bailey Island?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Bailey Island:

  • Peaks Island: 65 vacation rentals
  • Munjoy Hill: 60 vacation rentals
  • Willard: 30 vacation rentals
  • Falmouth Foreside: 22 vacation rentals
  • West Point: 18 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Bailey Island?

Vrbo offers a large selection of vacation rentals near lovely places in Bailey Island. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Bailey Island Bridge: 864 vacation rentals
  • Land's End Gift Shop: 811 vacation rentals
  • Cobwork Bridge: 851 vacation rentals
  • Higgins Beach: 1,376 vacation rentals
  • East End Beach: 1,312 vacation rentals

But there are many other points of interest around Bailey Island listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Cottages in Bailey Island?

Yes, of course. Vrbo has 57 Cottages in Bailey Island. Our other popular types of vacation rentals in Bailey Island include:

  • Houses: 67 rentals available
  • Cabins: 57 rentals available
  • Bungalows: 57 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Bailey Island?

Yes, you can select your preferred vacation rental with pool among our 5 vacation rentals with pool available in Bailey Island. Please use our search bar to access the selection of vacation rentals available.

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