Vacation rentals in Bailey Island

Quaint & Peaceful Designer's Oceanfront Cottage

Coco Cottage is a peaceful, cliffside escape with stunning 180° views of Harpswell Sound. Located at the end of a private road, it’s perfect for a designer’s retreat or family getaway. Three bedrooms—two queens, plus a twin/office combo—make it ideal for remote work or rest. Relax fireside and watch a movie, dine on the patio, read on the dock, or explore the amazing trails, beaches, seafood and sunsets of Harpswell. Enjoy oceanfront tranquility just 15minutes from Bowdoin College and Brunswick.

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Little Harbor Cottage

Waterfront cottage on perfect for the whole family. Newly renovated in 2024, this 5 bedroom, 2.5 bath house features ocean views from each bedroom and easy access to rocky beaches. Well appointed kitchen, high speed WiFi, and AC in each room make this the perfect place for your next Maine vacation. Centrally located on Bailey Island in Casco Bay, an easy home base for your coastal adventures. If the specific dates you’re looking for aren’t available, reach out to see if we have any flexibility

Mermaid's Chair | Private Beach | Hot Tub

*Please note: The hot tub is unavailable from October 27 through April. The booking guest must be at least 25 years old. This classic 1939 Maine camp sits directly on Casco Bay, offering a private dock, sweeping water views, and a saltwater hot tub, all on a quiet road. Properties like this don't come around often, and once you arrive, you’ll understand why. The dock places you right on the water, with one boat slip available for guests. Wolfe’s Neck State Park and Wolfe’s Neck Farm are nearby.

Slack Tide

Relax on the dock at this stylish private guesthouse and watch the sunset over an expansive tidal cove. This waterfront retreat features a private deck with gas grill and fire pit, a full kitchen and living area with fantastic water views, leather recliner, sofa and cable TV. The bedroom has an adjustable king Tempurpedic bed and a luxurious ensuite bathroom with a large shower, towel warmer, led mirror, hand-held bidet, heated toilet seat and washer/dryer. Wake up to breathtaking water views!

Sunset Stunner w/summer dock

Relax with the family at this peaceful place to stay. This cozy waterfront home offers a tranquil escape with breathtaking ocean sunset views that paint the sky each evening. Lots of windows and open concept living area provide uninterrupted vistas of the water, allowing golden light to flood the space. The wrap around deck just steps from the water's edge is an ideal spot for morning coffee or evening dinners as the sun dips below the horizon. This charming home blends comfort and nature.

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax with ocean views, warm up in the sauna or take a refreshing dip. Our cottage is part of Gurnet Village, an over 100-year-old working lobstering & oyster farming property on historic Route 24, between Brunswick & Harpswell. Expect boats, workers, road traffic, gear, and the occasional sounds & smells of a real Maine working waterfront. All rooms have ocean views, with access to the tidal beach & floating dock (May-Dec).

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Lovely Coastal Cottage on Quiet Cove

Wake up to gorgeous views and go to sleep under dark starlit skies. This modern and well-appointed coastal home is your chance to experience life on the water in Maine. Harpswell is a beautiful waterfront town with more coastline than anywhere else in Maine. When you're not relaxing on the deck overlooking the cove or, in winter, being cozy by the fire, you'll be able to explore the dozens of hikes on the peninsula and the year-round restaurants in nearby Bath or Brunswick.

Orchid Harbor, Bailey Island 3BR

Welcome to Orchid Harbor, a classic New England-style cottage home with stunning southerly views of Casco Bay. Perfectly located in the heart of Bailey Island, it's within walking distance of Cook's Lobster & Ale House, Morse's Seafood Grille, the historic Cribstone Bridge, and the Salt Cod Cafe. You'll love the breathtaking sunsets painting the sky. Enjoy easy water access, perfect for launching a kayak to explore the coast of Harpswell or combing the shoreline for treasures.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.