Holiday rentals in Orr's Island

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Top-rated holiday rentals in Orr's Island

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Top guest favourite

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 favourite

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 favourite

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 favourite

Guest house in Harpswell

4.95 out of 5 average rating, 462 reviews

Harpswell Studio on Waterview Property! Lobster!

6/23 - 7/1 - last minute pricing! 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!

Top guest favourite

Guest suite in Freeport

4.97 out of 5 average rating, 236 reviews

Waterfront Private Apartment only 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Superhost

Home in Harpswell

4.94 out of 5 average rating, 123 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!

Top guest favourite

Flat 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)

Superhost

Home in Harpswell

4.9 out of 5 average rating, 116 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 favourite

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 favourite

Home in Bridgton

5 out of 5 average rating, 104 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Guest favourite

Guest house 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 favourite

Home in Harpswell

4.98 out of 5 average rating, 204 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

Top guest favourite

Cabin in Harpswell

5 out of 5 average rating, 23 reviews

Waterledge Cottage - Orrs Island, Maine

MarcieRating, 5 stars1 month ago

Our family thoroughly enjoyed Waterledge. The home is lovingly decorated and comfortable. The kitchen is fully stocked with everything needed to cook complete meals. Indoor games and outdoor toys such as corn hole, croquet, kayaks… are also available. We enjoyed the stunning sunsets from the large porch, exploring the beach/waters edge at low tide and hiking. Everyone in our party of 6 wants to come back!

Guest favourite

Cottage in Harpswell

4.87 out of 5 average rating, 158 reviews

Quaint & Peaceful Designer's Oceanfront Cottage

JenniferRating, 5 stars2 weeks ago

One of the few Airbnbs that was better than the photos. Beautiful, all the things we needed, comfortable beds, gorgeous location.

Top guest favourite

Cottage in West Bath

4.92 out of 5 average rating, 77 reviews

Coastal Waterfront Tiny home in West Bath

LeahRating, 5 stars1 week 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!

Home in Phippsburg

5 out of 5 average rating, 4 reviews

Mid Coast Getaway w/ water views

KristenRating, 5 stars2 weeks ago

Fantastic stay this past weekend. Easy to find and flexible with check in. I got there an hour earlier than expected and it was no problem for me to go in early. Felt safe being a solo traveller. The views were insane! So so peaceful. Some considerations: Some outdoor comfortable seating would've been great. I could not lock anything because the locks of the sliders wouldn't open/close with the keys-I was afraid I would break a key off. So left wide open during the day. The couch, comfy, but stained. Only 2 towels were left-more would've been appreciated. I was freezing! So glad I brought an extra blanket. Leaky sink in kitchen. ZERO I mean ZERO water pressure-awful! Service is spotty in the area but the wifi was a big help. The price, views, communication, and flexibility cancels out any flaws of this place. With some TLC this place would be flawless. Thank you!

Top guest favourite

Flat in West Bath

5 out of 5 average rating, 40 reviews

Maine oceanfront getaway.

EvaRating, 5 stars2 weeks 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!

Guest favourite

Cottage in Harpswell

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!

Guest favourite

Cabin in Harpswell

4.85 out of 5 average rating, 34 reviews

Secluded Cabin

SarahRating, 5 stars9 months ago

This cottage was perfect for our family of 4. Quiet location with privacy is important for us - this property is part of an association, so there are other houses nearby, but there was a good buffer of trees in between. Susan provided helpful info and recommendations, and the cottage had everything we needed. Beautiful location, with lots of places to visit within 30-40 minutes’ drive (or less than 10!). This location is not within walking distance to a sandy beach, but the association does have a small access to a rocky waterfront, so that was nice. We’d definitely stay here again if we wanted to visit this part of Maine in the future.

Flat in Harpswell

4.83 out of 5 average rating, 266 reviews

Sunny Apartment on the Ocean.

RitaRating, 5 stars2 weeks ago

Jane and Rick's place was wonderful - immediately felt like home! Really friendly and hospitable couple. The place is much bigger than the photos suggest. The deck on the water is a dream come true. Would love to stay again!

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Holiday rentals in Orr's Island

Top-rated holiday rentals in Orr's Island

Holiday rentals for every style

Popular amenities for Orr's Island holiday rentals

Other great holiday rentals in Orr's Island

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