Holiday rentals in Bailey Island

4.99 out of 5 average rating, 396 reviews

Cottage in Pownal

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

4.99 out of 5 average rating, 135 reviews

Cabin in Georgetown

Sauna+Near Beach+Pond+Outdoor Shower+FirePit+A/C

Come relax at Pine Cabin, one of two cabins on 8 acres with a pond minutes from one of the best beaches in Maine. Unwind in your private outdoor cedar glass sauna w/forest views & refresh in our seasonal outside shower! * Minutes to Reid State Park & 5 Island🦞 * Fire Pit * Family Own & Run * Gas Grill * Private Bedroom w/Queen Bed * Loft w/Queen Bed & Record Player * Rain Shower * Custom cabinets & couch * Screen porch * AC/Heat * EV charger * Fast Wifi * Beach Gear * Smart TV * Generator

4.86 out of 5 average rating, 7 reviews

"Footnote" A unique quintessential Maine cottage

New Listing !! "Footnote" is an ideal quintessential 1920's Maine cottage located on Orr's Island, ME. Stunning ocean views & breathtaking sunsets. The kitchen & bathroom are new with new appliances. The cottage sleeps 4, one queen bed, 2 twins. Living room, sitting room, screened in room & great outside deck. Ocean views from most every room ! For the adventurous there is a steep trail alongside of the property leading to the rocky shore. Close to Brunswick. Sorry no pets, washer or dryer.

4.89 out of 5 average rating, 54 reviews

Basin Cove Retreat: Perfect to explore Mid-Coast

Welcome to our peaceful waterfront cottage on Basin Cove, perfect for year-round relaxation. This cozy 2-bedroom, 1-bath retreat offers serene water views and breathtaking sunsets. Just 12 miles from Brunswick, 30 mins from iconic LL Bean in Freeport, and an hour from Portland, you'll enjoy both tranquility and convenience. Ideal for a quiet winter escape or a summer adventure. The cottage is close to Live Well Farm and Bowdoin College, providing the perfect blend of relaxation and exploration.

4.96 out of 5 average rating, 23 reviews

Home in Georgetown

Breathtaking Bay Views!

Enjoy glorious sunsets over Sagadahoc Bay on Indian Point at the tip of Georgetown Island! Walls of glass bring the outside in to this 3 bed, 2 bath contemporary home where the only decisions you'll make are whether to spend your days at the beach, on the ocean, or exploring the trails... Later in the day you need to choose whether to grill under the stars, take a short drive to one of the great local spots, or head to Five Islands on the wharf for some of the best lobster Maine has to offer!

Superhost

4.94 out of 5 average rating, 122 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

4.95 out of 5 average rating, 462 reviews

Guest house in Harpswell

Harpswell Studio on Waterview Property! Lobster!

Available dates in late June! Cottage Style Studio! Clean, spacious, colorful, comfy, bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away. Enjoy the trails in the woods with spectacular views or walk on the beach at one of the state parks! So beautiful!

4.98 out of 5 average rating, 61 reviews

New Modern Cottage with Ocean Views & Wildlife

The Salty Roost, a modern Scandinavian-inspired guest cottage is positioned on one acre adjacent to our main home in a coastal neighborhood. This property offers distance water views of Middle Bay, dock/water access, on-site parking, grill, hammock chairs, kitchen with all the amenities, WIFI, washer and dryer combo unit, hardwood floors. The cottage is minutes from great restaurants, breweries, hiking trails, and shopping. The most amazing sunsets will surely bring joy to your stay.

4.98 out of 5 average rating, 135 reviews

Yurt in Chebeague Island

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

Superhost

4.9 out of 5 average rating, 115 reviews

Rising Tide Times - quintessential Maine cottage

Out of State guests please read the Maine State COVID-19 restrictions currently in affect. 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!

Superhost

Flat in Harpswell

4.92 out of 5 average rating, 12 reviews

Sunset Hideaway on Bailey Island

Welcome to Sunset Hideaway, a comfortable one bedroom apartment sleeping 4 guests. 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.

4.98 out of 5 average rating, 202 reviews

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.

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Other great holiday rentals in Bailey Island

4.87 out of 5 average rating, 157 reviews

Quaint & Peaceful Designer's Oceanfront Cottage

GeorgiaRating, 5 stars3 weeks ago

My partner and I had a lovely stay at this home! It was beautifully decorated and the view was gorgeous, even in the fog. We especially enjoyed the cozy gas fireplace.

LilyRating, 5 stars2 weeks ago

Cricket Lodge

What a beautiful house and location! We feel so lucky that we found the Cricket Lodge. Nikoline was a lovely and responsive host, and the home was even more charming in person. My friends and I are already talking about trying to plan a trip back. Thank you so much!

4.99 out of 5 average rating, 141 reviews

Guest house in Yarmouth

Private Guesthouse in the Woods

RachelRating, 5 stars4 days ago

We had a great stay here! The place was perfect location and in a very nice area. Very quiet and close by to a lot of things. Also, very clean!

4.98 out of 5 average rating, 42 reviews

On Island Time Cottage

KatieRating, 5 stars9 months ago

Cathy is such a great host. Her space had so many kid-friendly details (toys, books, art supplies, reading lamps). She also lent us the an outdoor wagon and even a Tonka truck for my toddler - both big hits. The three-ring binder with information and recommendations was well organized and accessible. Cathy was more than happy to give recommendations for good places to hike. The area has so many beautiful and accessible trails, including a nature preserve right across the road from the Airbnb cottage. Popham beach is a good 45 minute drive, but Cedar Isle beach is just 5 minutes away and also has nice sand with far fewer seagulls. Great place to stay for young families and nature-lovers!

5 out of 5 average rating, 7 reviews

Coastal Home away from Home

TerriRating, 5 stars2 weeks ago

This is an absolutely beautiful home! It was very comfortable and had an amazing view from the back porch. The home was very clean and had all of the amenities that we needed. Kathryn was extremely responsive to all of our questions and needs. We would most definitely stay here again if we travel back to the area.

Flat in Harpswell

4.83 out of 5 average rating, 265 reviews

Sunny Apartment on the Ocean.

CarissaRating, 5 stars2 weeks ago

Jane’s place was lovely and peaceful. Check in was smooth and the entire stay was relaxing

5 out of 5 average rating, 5 reviews

Cedar Cottage on Quahog Bay

MikeRating, 5 stars8 months ago

Absolutely beautiful setting over looking a bay full of lobster boats and sailboats. You can enjoy your morning coffee on the deck right outside your den, in some large Adirondack chairs under some trees, or out at the end of a long floating pier. Miles and miles of hiking trails are minutes away. We saw large flocks of turkeys every day within a couple of hundred yards of the cabin. We saw deer and seals on hikes. When you find something like this, there’s no reason to keep looking for something better. You’re not going to find it.