Holiday rentals in Long Island

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Top-rated holiday rentals in Long Island

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Top guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 395 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

Superhost

Cottage in Cape Elizabeth

4.85 out of 5 average rating, 148 reviews

Kettle Cove, Crescent Beaches, Trails, Peaceful

The Kettle Cove neighborhood is beautiful, relaxing, safe, quiet. Kettle Cove and Crescent beaches are a stroll from the home. We live in a 200 year-old farmhouse, and we love to host guests at our guesthouse, which is separate and private. The wide lawn, fire-pit, and BBQ are open for our guests. We are quiet, friendly, inviting, and respectful of our guests' space and privacy. The Red-Brick patio is exclusively reserved for our guests. ***WE REQUIRE FRIDAY/SATURDAY/SUNDAY NIGHTS STAY***

Superhost

Loft in Portland

4.9 out of 5 average rating, 294 reviews

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

Top guest favourite

Yurt in Chebeague Island

4.98 out of 5 average rating, 135 reviews

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.

Top guest favourite

Flat in Peaks Island

4.98 out of 5 average rating, 151 reviews

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Top guest favourite

Flat in Cape Elizabeth

4.98 out of 5 average rating, 264 reviews

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

Guest favourite

Guest suite in East End

4.92 out of 5 average rating, 282 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Top guest favourite

Tiny home in Portland

4.96 out of 5 average rating, 478 reviews

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

Guest favourite

Guest suite in South Portland

4.92 out of 5 average rating, 253 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

Guest favourite

Cabin in Kennebunk

4.97 out of 5 average rating, 139 reviews

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

Guest favourite

Guest house in Peaks Island

4.95 out of 5 average rating, 133 reviews

Tiny Cottage Hideaway, close to everything

A studio built in 1920 turned one-bedroom Guest Cottage, full of charm, on "Peaks Island". Within 5 minutes walking distance to the ferry, restaurants, a beach and shopping "Down Front". Perfect for 1-2 people and possibly a third. The Tiny Cottage is an off-the-beaten-path Maine experience. Peaks Island is an 18 min ferry ride from Portland.

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Popular amenities for Long Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Long Island

Flat in South Portland

5 out of 5 average rating, 3 reviews

Charming Victorian Getaway With Private Patio

TravisRating, 5 stars4 days ago

We had a wonderful visit at Colleen’s place!! The place is beautiful and very comfortable. The private deck area is a beautiful spot and so relaxing. Everything inside was given great attention and the art displayed is beautiful. You will not regret choosing this this as your vacation destination!!!

Home in Long Island

5 out of 5 average rating, 7 reviews

Waterfront Home on Long Island -Golf Cart Included

ColbyRating, 5 stars33 months ago

Such a beautiful house in such a special place. The listing looked great but wow… it’s so much better when you get there. Scooting over to the beach for the day couldn’t be easier with the golf cart and then you get to watch and awesome sunset over the bay every night. It’s wild. We can’t wait to come back.

Top guest favourite

Guest house in Freeport

5 out of 5 average rating, 65 reviews

Mast Landing Cottage

ClarkRating, 5 stars2 weeks ago

The cottage was perfect for our week in Freeport. The cottage was well equipped, the yard was very well kept, and the parking was great. We worked remote some while we were there and the dedicated desk and internet speed was perfect. I would highly recommend a stay here!

Cottage in Peaks Island

4.62 out of 5 average rating, 26 reviews

Seaview Cottage/Quintessential Maine With a View

JamisonRating, 5 stars11 months ago

Mary is an excellent host. Very friendly, helpful and responsive. The house was not just clean and comfortable but it was obviously decorated with love and care. The Sun Room was an especially lovely place to be , with amazing views of Great Diamond and the bay…like a private tree house with lots of light. Also, the kitchen was VERY well appointed…great for cooking.. a special nod to the back deck…that’s where to find a cool breeze and a view of the very pretty gardens.

Guest favourite

Cottage in Long Island

4.8 out of 5 average rating, 46 reviews

Picturesque Maine water view Long Island

KristaRating, 5 stars9 months ago

Was so grateful to be back on the island, and Rebecca was so accommodating to our needs! we loved the house, the big deck, and how easy it all was! we are long timers to long Island, and really enjoyed our stay there! Rebecca is a great host and super chill! will come back if we are able!

Home in Phippsburg

New place to stay

Mid Coast Getaway w/ water views

Sarah CatherineRating, 5 stars2 weeks ago

We had an incredible stay! The location was unbelievable, and the many windows made it so no matter where we were sitting, we had a gorgeous view. We loved being able to walk right across the street for oysters, and our dog loved exploring the area. We couldn’t be more grateful for the best weekend getaway.

Flat in Peaks Island

5 out of 5 average rating, 23 reviews

Beach Front, Waterfront, Ferry Beach

PattiRating, 5 stars2 weeks ago

I can’t wait to come back! I can not say enough about location, host, island, beds, bathroom, kitchen, ……… Recommend highly

Home in Long Island

5 out of 5 average rating, 8 reviews

The Long Island Maine House - Family Island Time!

SeanRating, 5 stars34 months ago

Great place, slept 8 wonderfully. Very accessible to the different spots on the island. Plenty of chairs and beach accessories. Stephanie was very responsive and her instructions were clear. Kitchen was fully stocked with plenty of dishes etc. The only thing to keep in mind during your stay is to plan for the ferry in the morning on your check out date it comes quickly! So ensure your cleaning is done prior! Couldn’t recommend it more 10/10

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Quick stats about holiday rentals in Long Island

Total rentals
70 properties
Nightly prices starting at
₹6,851 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Holiday rentals in Long Island

Top-rated holiday rentals in Long Island

Holiday rentals for every style

Popular amenities for Long Island holiday rentals

Other great holiday rentals in Long Island

Quick stats about holiday rentals in Long Island

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Destinations to explore