Holiday rentals in Orr&#x27;s 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

Cottage in Harpswell

"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.

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!

4.92 out of 5 average rating, 120 reviews

Flat in Orr's Island

Shore House, Posey Unit - Ocean Front Property

On top of the world in this second level unit of a multi-unit house. Lovely views from the scenic deck over looking a working wharf on Garrison Cove and Casco Bay. The unit has 2 bedrooms (additional accommodations to sleep up to 6), one bath, and a full kitchen and breath taking sunsets Dogs allowed upon approval. Must not be big barkers and well behaved pets. We want to be courteous of all renters and their pets. Weekly rentals preferred in July and August months (Saturday - Saturday)

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, 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!

4.91 out of 5 average rating, 116 reviews

Tiny home in Bowdoinham

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

4.97 out of 5 average rating, 510 reviews

Cabin in Freeport

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

4.93 out of 5 average rating, 153 reviews

Guest house in Brunswick

Modern Brunswick Cottage near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.

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 Orr's Island

4.95 out of 5 average rating, 20 reviews

Guest suite in Freeport

Studio Apartment in Freeport

SarahRating, 5 stars1 day ago

We had a great stay at Dustin and Brianna’s! It’s spotless and smells fresh! Our four year old loved the fun bed and books to read! Would definitely book again!

5 out of 5 average rating, 32 reviews

Guest house in West Bath

Spruce Ledge Boathouse

JenniferRating, 5 stars2 weeks ago

We loved every minute we spent in this beautiful cabin. The views were stunning and the cabin was cozy. It's a truly delightful spot.

4.87 out of 5 average rating, 157 reviews

Cottage in Harpswell

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.

4.98 out of 5 average rating, 61 reviews

New Modern Cottage with Ocean Views & Wildlife

MackenzieRating, 5 stars8 months ago

We can’t say enough good things about this stay. We came for our honeymoon, and were met with flowers and a few other treats from the host as a gift. How sweet! As far as the property, the cottage is perfectly sized for two or three, and is designed delightfully. It is on a shared lot with the family’s primary residence , but feels very comfortable and private. A close by walk to the water as well. Inside, you will find everything you could ever need from pots and pans, spices, towels, and the best recommendations for the area. We’d build our own version of this cottage to take home with us if we could. We hope to one day be back and will always remember our amazing time in Harpswell.

4.92 out of 5 average rating, 77 reviews

Cottage in West Bath

Coastal Waterfront Tiny home in West Bath

LeahRating, 5 stars4 days ago

What an awesome airbnb! The views are stunning and surroundings couldn’t have been more peaceful. The cottage itself was exceptional and had everything I needed and more. Wish I could've stayed there longer! 10/10 would recommend this place to anyone!

5 out of 5 average rating, 40 reviews

Flat in West Bath

Maine oceanfront getaway.

EvaRating, 5 stars1 week ago

We’d knew we’d stumbled upon something extra special after reading one excellent review after another here…and yet still hadn’t fully imagined how perfect it would all be in person. Our anniversary weekend started with the beautiful and relaxing drive out to the point where we were warmly welcomed by Deborah who had a wealth of local tips and answered our every question. Highlights: Spectacular views over the water and inviting spaces to relax in the lovely garden; the clean, relaxing, beautifully and uniquely designed studio; dinners at Enoteca Athena and Blue (Grey Havens Inn); easy hikes, notably Morse Mountain and out to the beach… But the best? Deborah. With her thoughtfully placed vases of flowers, sweet offerings and treats, and especially her contribution to the overall feeling of connection in this special part of Maine. Thank you!