Orr's Island vacation rentals

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Top-rated vacation rentals in Orr's Island

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Top guest favorite

Cottage in Pownal

4.99 out of 5 average rating, 396 reviews

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.

Top guest favorite

Cabin in Georgetown

4.99 out of 5 average rating, 135 reviews

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

Guest favorite

Cottage in Harpswell

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.

Top guest favorite

Apartment in Orr's Island

4.92 out of 5 average rating, 121 reviews

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)

Top guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 462 reviews

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!

Superhost

Home in Harpswell

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!

Guest favorite

Tiny home in Bowdoinham

4.91 out of 5 average rating, 116 reviews

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.

Top guest favorite

Townhouse in Harpswell

4.98 out of 5 average rating, 52 reviews

Tower Hill House Harpswell, Orr’s Island, Maine

Gather with family (including pooches!) and friends at our airbnb in Maine. Explore the coast, shops and restaurants or simply relax! Curl up with a book in the cozy reading nook, play board games or put together a puzzle on the game table. Enjoy a game of croquet or corn hole, dine alfresco, sit by the fire pit on a chilly evening. Source ingredients from local farmers and fishermen and prepare a meal in the fully equipped kitchen or enjoy dining at our local restaurants.

Superhost

Cottage in Harpswell

4.89 out of 5 average rating, 156 reviews

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.

Guest favorite

Cabin in Freeport

4.97 out of 5 average rating, 510 reviews

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

Guest favorite

Guesthouse in Brunswick

4.93 out of 5 average rating, 153 reviews

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.

Top guest favorite

Home in Harpswell

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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Popular amenities for Orr's Island vacation rentals

Gym

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Other great vacation rentals in Orr's Island

Top guest favorite

Home in Freeport

5 out of 5 average rating, 47 reviews

Waterfront Cottage in Freeport

BrianRating, 5 stars2 weeks ago

Beautiful location on the water with stunning views, tranquil and peaceful with plenty of osprey and bald eagle sightings (there is a nest across the bay on Pettingill Island visible from the property). The house is very well-appointed and well-decorated. Irena was very communicative and responsive, and the house directions are clear and complete. We would stay there again. Thank you!

Top guest favorite

Apartment in Phippsburg

5 out of 5 average rating, 29 reviews

Twin Heart Treetop

GregRating, 5 stars2 weeks ago

It was our first time using Airbnb and we couldn't have been luckier to find TwinHeart TreeTop hosted by Buck and Marie. It is a very clean,quiet and comfortable place. Marie and Buck are fantastic hosts,so nice and very accommodating. The area around Small Point is magical with so many things to see and do. The private beach is spectacular,we even saw some gray seals feeding. We'd love to be able to return. Thanks again to Buck and Marie for allowing us to stay in their special place.

Top guest favorite

Guesthouse in West Bath

5 out of 5 average rating, 32 reviews

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.

Guest favorite

Cottage in Harpswell

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.

Top guest favorite

Cottage in West Bath

4.92 out of 5 average rating, 77 reviews

Coastal Waterfront Tiny home in West Bath

LeahRating, 5 stars5 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!

Guest favorite

Cabin in Hope

5 out of 5 average rating, 15 reviews

Cozy Lakefront Cabin - Hope Floats

WillRating, 5 stars2 weeks ago

Spent a relaxing long weekend at the cabin. Idyllic location right on the water with plenty to do outside. We enjoyed making fires, fishing, and exploring in the canoe. Inside, the cabin was thoughtfully decorated and very comfortable. Camden is nearby for a nice dinner or a stroll and shopping downtown. Acadia is also close enough for a day trip. Checkin/checkout was very straightforward, and the host was helpful and quick to answer any questions. Hope to visit again!

Top guest favorite

Place to stay in West Bath

5 out of 5 average rating, 35 reviews

Cozy Coastal Cabin -in the woods

SaraRating, 5 stars1 week ago

First time renting on Airbnb, it couldn’t have been a more perfect experience. The cozy cabin on the cliffs of Maine was beyond anything I could’ve imagined. Stephanie & Heather thought of everything; welcome snacks, dog treats, water, things to do,etc. They even had binoculars, we used on a bald eagle diving into water. Being able to use their kayaks (no charge), made packing & planning much easier. The peaceful surroundings & natural beauty made it easy to disconnect & relax. We saw so many jellyfish in the ocean and they were beautiful! On check-out morn, Stephanie messaged us to say we stay later in day because no one was checking in today, it was the nicest day. That extra time meant everything, we ended up leaving around 4pm with no extra charge. The level of kindness & hospitality is rare & so appreciated. This stay was absolutely unforgettable, we will 100% be coming back. Thank you, Stephanie & Heather, for creating such a peaceful, thoughtful, & welcoming escape.

Top guest favorite

Apartment in Cape Elizabeth

4.99 out of 5 average rating, 73 reviews

Crescent Beach Gardens

AmyRating, 5 stars1 week ago

The views were amazing and the place was perfect! They’ve thought of everything (beach chairs, extra linens, coffee) and the flowers and birds make the property even more lovely. I stayed with my daughter and there is privacy within the space. The beach is a five minute walk from the house. We will definitely stay again!

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Orr's Island vacation rentals

Top-rated vacation rentals in Orr's Island

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