Holiday houses in Portland

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.

4.98 out of 5 average rating, 152 reviews

Apartment in East End

Modern Luxury with Bay Views * 5 Star Location!

Well-appointed, high-end private apartment with wide plank pine floors sourced from Western Maine, luxury bathroom and bedroom. Shared patio with grill and fire pit. A short walk to the Eastern Prom or restaurants of the Old Port and Washington Street. I pay attention to details such as cleanliness, local coffee, quality linens, furniture and furnishings. Queen bed with a view of the harbor. This is a non-smoking, non-cooking space. Not suitable for infants children. Hi speed internet.

4.9 out of 5 average rating, 229 reviews

Apartment in Oakdale

Bright & Sunny Apartment with Patio

Centrally located in Portland, just steps away from USM/Maine Law, Back Bay, Bird & Co., Rose Foods, and other Oakdale gems. This apartment features personal touches and is stylishly furnished with attention to detail. Located on a quiet street in the Oakdale neighborhood, it is one of the best locations - as you can walk everywhere. It is a short Lyft or Uber to the famous Old Port. Feel the charm of a quiet neighborhood while also being close to city center. License #: STHR-004014-2022

4.96 out of 5 average rating, 319 reviews

Guesthouse in Portland

Beautiful large studio on the ocean.

PLEASE NOTE WE HAVE A 4 NIGHT MINIMUM STAY DURING THE SUMMER. Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests so if you'd like to book please introduce yourselves and let us know who is coming. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

Guest suite in Downtown Portland

4.96 out of 5 average rating, 693 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

4.96 out of 5 average rating, 157 reviews

Guest suite in Saco

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

4.78 out of 5 average rating, 577 reviews

Apartment in West End

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 suite in Ferry Village

5 out of 5 average rating, 254 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

4.92 out of 5 average rating, 282 reviews

Guest suite in East End

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 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 !

Hotel room in Downtown Portland

4.92 out of 5 average rating, 195 reviews

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft hosted by The Docent’s Collection. Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

4.97 out of 5 average rating, 139 reviews

Cabin in Kennebunk

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."

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Portland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Portland's top sights

Willard Beach45 locals recommend

Portland Museum of Art59 locals recommend

Peaks Island76 locals recommend

Other great holiday rentals in Portland

5 out of 5 average rating, 52 reviews

Cabin in Freeport

The Maine Frame: Cozy Firepit 7 Min to L.L. Bean

DennisRating, 5 stars3 days ago

Private and relaxing, I enjoyed really peaceful. The roster made so easy with all recommendations and resources we needed, me and my spouse loved it was really good experience “ we recommend”

5 out of 5 average rating, 17 reviews

Barn in Scarborough

Stunning 1 bedroom barn.

MariaRating, 5 stars7 months ago

I had a lovely stay at thr barn. Check in was smooth, space was very clean, the location was perfect. Lots of nature and beautiful park/trail at walking distance with a very quick drive to beach! Christopher and Nathalie are great hosts! They were responsive and also very accommodating with my needs. This is a wonderful Airbnb for a peaceful and serene nature retreat while also being close to Portland!

4.87 out of 5 average rating, 464 reviews

Hotel room in West End

Eateries, nightlife, galleries – walk to it all

MeganRating, 5 stars3 days ago

Aloft was a great place to stay! The room looked exactly how it was described and shown. The location of Aloft was great, it was very private and quiet. Walkable to many restaurants, shops, and waterfront locations. We had a great time staying with Aloft at their location in Downtown Portland. We look forward to our next time in the area!

Private room in Deering Center

4.87 out of 5 average rating, 659 reviews

The peaceful attic bedroom

AshleyRating, 5 stars2 weeks ago

Laura’s home was BEAUTIFUL! Straight out of a story book! We stayed there for one night and it was the perfect beginning to our trip! She was also very responsive and helpful. Thank you, Laura!

5 out of 5 average rating, 9 reviews

Apartment in West End

West End apartment with parking

HannahRating, 5 stars5 days ago

Very nice place with full kitchen and easy location to get to restaurants and concert venues. Super friendly host! Would definitely recommend.

Apartment in Downtown Portland

5 out of 5 average rating, 4 reviews

Old Port Loft - 302

MarieRating, 5 stars1 week ago

Great location, close to so much to do! Loved the bed - super comfy! It is in the heart of a lot- so at night it is bright from lights on resteraunts and there is noise- but we knew what to expect so it didn’t bother us. If you aren’t used to “city living” bring some ear plugs and an eye mask and you will be fine! Host was very responsive and even let us check in early as our train was scheduled earlier than we had planned. Would definitely stay again!

5 out of 5 average rating, 68 reviews

Apartment in Back Cove

Luxe Eco Studio near Back Cove

AmyRating, 5 stars6 days ago

Hands down my favorite Airbnb! Emma and Dave are thoughtful, responsive hosts whose space is a tranquil and restorative. It is beautifully designed with comfortable beds, furniture and perfectly layered lighting. The neighborhood is very quiet and we slept soundly every night. In fact, I feel like we did a little less sightseeing than we normally would have because we just didn’t want to leave! Our daughter loved the cozy sleeping nooks. Every detail was considered. I’ve already recommended this location to a couple of friends who live in Boston and would gladly stay again if we find ourselves back in ME. Loved every minute of our stay! Thanks, Emma and Dave!