Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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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

Flat in Downtown Portland

4.98 out of 5 average rating, 313 reviews

Light-Filled Getaway with Private Porch

Spacious (1100 sqft), updated early Victorian (1838) apartment bordering the Arts District in Portland's historic and beautiful downtown West End. The apt. has great natural light, ample workspace, free on-street parking, a private garden entrance, and a sheltered, leafy screened porch. With a Walk Score of "95-A Walkers Paradise", you'll be able to stroll to nearby restaurants, cafes, museums, parks and Old Port. Then, return to a relaxing space that you'll be very happy to call 'home'!

Guest favourite

Guest suite in Downtown Portland

4.96 out of 5 average rating, 688 reviews

Studio, Walk to everything, Parking

5 to10 minute walk to all Portland has to offer; restaurants, breweries, galleries, shops, and famers markets. Located in a vibrant, safe, and transitional neighborhood. Steps from Portland's Arts district + Congress Street, (Portland Public Market, Broken Arrow, Regards, Portland School of Art). Home to Batson River Brewing & Distilling, ISA, Wilson BBQ. Short walk to downtown and the Old Port. Park your car and leave it for the duration of your stay. License # 20180110-ST

Top guest favourite

Guest suite in Saco

4.96 out of 5 average rating, 157 reviews

Suite LunaSea

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

Guest favourite

Flat in East End

4.93 out of 5 average rating, 629 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Superhost

Flat in West End

4.78 out of 5 average rating, 576 reviews

Downtown Studio, Walk Everywhere, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

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!

Guest favourite

Tiny home in Portland

4.96 out of 5 average rating, 480 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

Top guest favourite

Flat in East End

4.97 out of 5 average rating, 574 reviews

Cozy & Comfortable apartment in a perfect location

Bright sunny 1 bedroom private apartment in a quiet, Owner Occupied building. Perfect location. A short walk to Duckfat, Eventide and the rest of Portland. Top floor with full kitchen, work/desk area, comfortable living room, full bath with tub and shower, bedroom with a comfortable Queen bed. If you're a book lover, you'll enjoy it even more! Includes Reserved off street parking. Portland City License #STHR-000980

Guest favourite

Guest suite in South Portland

4.92 out of 5 average rating, 255 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

Flat in East End

4.87 out of 5 average rating, 254 reviews

Petit Pad Atop Munjoy Hill+Steps to Eastern Prom!

Our space is small yet cozy. Tiny living at its best. It's bright with many windows lending a glimpse of Casco Bay, and the third floor level welcomes the cool breeze off the water. Well appointed with everything you need to be comfortable and feel at home. A perfect home base while you explore Portlands Munjoy Hill neighborhood and beyond! We know you'll love it!

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."