Holiday rentals in Chebeague Island

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Top-rated holiday rentals in Chebeague Island

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Guest favourite
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.
23–30 Jan
$322 SGD per night
4.99 out of 5 average rating, 320 reviews
Guest favourite
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. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.
22–29 Jul
$161 SGD per night
4.97 out of 5 average rating, 101 reviews
Guest favourite
Guest house in Portland
Beautiful large studio on the ocean.
Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.
28 Apr – 5 May
$179 SGD per night
4.95 out of 5 average rating, 277 reviews

Popular amenities for Chebeague Island holiday rentals

Stay near Chebeague Island's top sights

Chebeague Island Inn12 locals recommend
Doughty's Island Market4 locals recommend
Slow Bell Cafe5 locals recommend
Great Chebeague Golf Club3 locals recommend
The Niblic & Gallery3 locals recommend
Museum of Chebeague History, South Road, Chebeague Island, ME3 locals recommend

Other great holiday rentals in Chebeague Island

Guest favourite
Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
10–17 Feb
$77 SGD per night
4.94 out of 5 average rating, 326 reviews
Guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
6–13 Jun
$550 SGD per night
5.0 out of 5 average rating, 202 reviews
Superhost
Home in Yarmouth
Cousins Island Summer Getaway
28 Jul – 4 Aug
$333 SGD per night
4.84 out of 5 average rating, 32 reviews
Guest favourite
Guest house in Yarmouth
Private Guesthouse in the Woods
3–10 May
$189 SGD per night
5.0 out of 5 average rating, 59 reviews
Superhost
Island in Cumberland
Bates Island: Casco Bay Glamping Experience
6–13 Dec
$1,171 SGD per night
4.91 out of 5 average rating, 11 reviews
Guest favourite
Guest house in Cumberland
Cozy & Convenient Cumberland Guest Cottage
20–27 Mar
$148 SGD per night
4.94 out of 5 average rating, 82 reviews
Guest favourite
Cottage in Long Island
Seacret Seaside Cottage, charming 3 bedroom
7–14 Sep
$803 SGD per night
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Yarmouth
Sweet 1-Bedroom Apartment in Vintage Village Cape
30 Mar – 6 Apr
$169 SGD per night
4.96 out of 5 average rating, 91 reviews
Guest favourite
Flat in Falmouth
Sweet 2-story 1910 Bungalow near Portland, Beaches
12–19 Nov
$145 SGD per night
5.0 out of 5 average rating, 37 reviews
Guest favourite
Guest house in Freeport
Mast Landing Cottage
28 Jan – 4 Feb
$150 SGD per night
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Harpswell
Brand new year-round oceanfront home with beach.
1–8 Feb
$1,332 SGD per night
5.0 out of 5 average rating, 80 reviews
Guest favourite
Cottage in Yarmouth
Demure coastal cottage steps to private beach.
27 Dec – 3 Jan
$509 SGD per night
4.95 out of 5 average rating, 22 reviews

Destinations to explore