Holiday 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.

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

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!

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

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.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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.

Mermaid's Chair | Private Beach | Hot Tub

*Hot tub not available after October 27- April This is a rare one. A classic 1939 Maine camp sitting directly on Casco Bay with a private dock, sweeping water views, and a saltwater hot tub, all on a quiet private road. Properties like this don't come around often, and once you're here, you'll understand why. The dock puts you right on the water, with one slip available for guests. Wolf's Neck State Park and Wolf's Neck Farm are a short walk away, and Downtown Freeport.

Sunset Hideaway on Bailey Island

Welcome to Sunset Hideaway, a comfortable one bedroom apartment sleeping 4 guests (1 queen bed, 1 pull-out). Perfectly located in the heart of Bailey Island within walking distance of local food options. The large lawn just across the street lends to easy water access, perfect for launching a kayak to explore the coast of Harpswell or combing the shoreline for treasures. You'll love the stunning sunsets painting the sky with beautiful purple, rose, and orange hues.

Bird Watching Paradise Harpswell

Gorgeous brand new 1BR in law unit above the garage in a waterfront property with 1.6 acres big lawn! It is so peaceful just to look outside with the big windows or just grab a drink and have some fresh air on the deck. Watch the wild animal crossing the lawn, maybe you will spot a red fox, ducks and geeks are regular visitors :) Also enjoy the Maine wood trails and bay trails around, this is truly a great place for getaway and enjoy the nature!

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.

Rising Tide Times - quintessential Maine cottage

Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!