Holiday houses 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, 397 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.

Guest favourite

Apartment in South Portland

4.94 out of 5 average rating, 142 reviews

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

Guest favourite

Guest suite in Portland

4.97 out of 5 average rating, 214 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Guest favourite

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

Top Guest favourite

Guest suite in Saco

4.96 out of 5 average rating, 158 reviews

LunaSea Suite

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

Superhost

Apartment in West End

4.78 out of 5 average rating, 578 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

Apartment in East End

4.84 out of 5 average rating, 247 reviews

Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom

Beach vibes in this cozy space make for a comfortable home base while you explore Portland's Munjoy Hill neighborhood. The apartment is situated in the East End, a short walk to the Eastern Promenade, local grocery, great restaurants and bakeries. Head to the East End Beach, or paddle to the islands in Casco Bay. Walk to the Old Port from this quiet neighborhood in 15 minutes or head over to Washington Ave, for amazing food, distilleries and breweries!

Top Guest favourite

Guest suite in South Portland

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.

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

Guesthouse in Brunswick

4.94 out of 5 average rating, 155 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.

Guest favourite

Guest suite in South Portland

4.92 out of 5 average rating, 256 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."

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

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

Superhost

Apartment in Portland

4.85 out of 5 average rating, 60 reviews

Cozy Back Cove Apartment - 5 min from Old Port

TanyaRating, 5 stars2 weeks ago

My husband & I really enjoyed our stay at Nicholas's place. Only a 5-min. drive to downtown so easy access to everything ($5 All Day Parking Lot at the end of Commercial St (near Becky's Diner) will save you a ton! Lots of great food (The Friendly Toast for amazing breakfast, Luke's for best lobster rolls, Coffee Me Up for lattes/bfast sammies). There is a cute coffee/smoothie shop (The Conscious Cup) right next door to the air bnb. An ice cream shop &Thai restaurant also right there. Do a trolley tour that goes to the Portland Head Light & take the ferry to Peak's Island for a nice boat ride. Some traffic noise being located right at the corner but nothing extreme. Getting in/out was easy, but the light by our stairs was out so we walked up carefully at night. Extra bedding/towels were mentioned but only a fitted sheet, pillowcases&a new pillow at the back of the utility closet were present. The extra bed pillows/fitted sheet saved us as night. Convenient smart TV. Overall A!:)

Top Guest favourite

Cabin in Freeport

5 out of 5 average rating, 53 reviews

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

TaylorRating, 5 stars2 days ago

It was our first time visiting Maine and to be able to stay at this adorable cabin was the cherry on top of a great trip. It was private, clean and beautiful - what more do you need? Sarah was a super responsive host and really made us feel right at home with all of the little touches. We can’t wait to stay here again!

Apartment in East End

4.85 out of 5 average rating, 447 reviews

Modern East End studio, perfect Portland home base

JacobRating, 5 stars2 weeks ago

Ian’s place was great! Very conveniently located and perfect for a long weekend for the two of us!

Guest favourite

Apartment in Portland

4.83 out of 5 average rating, 12 reviews

Roof Deck | Parking | 5 Min Downtown

AmberRating, 5 stars1 week ago

Great space and beautiful set up! The place is exactly as it looks in the photos. It’s located in a quiet and peaceful neighborhood, and is only a short drive to downtown Portland. A perfect rooftop deck to read on and catch some rays. The hosts were responsive and the instructions were clear. Very easy check in and check out process. Would highly recommend!

Guest favourite

Apartment in West End

5 out of 5 average rating, 6 reviews

West End Nest with Parking

JakeRating, 5 stars2 days ago

Great location, it was great to have parking. Perfect for someone who just needs a place to lay their head and is interested in spending time out and about. Very clean and cozy apartment with a lot of character, just be prepared to walk up to the third floor; although it didn’t bother us at all. A real find.

Top Guest favourite

Apartment in Cape Elizabeth

4.99 out of 5 average rating, 75 reviews

Crescent Beach Gardens

JohnRating, 5 stars1 week ago

Simply wonderful, the perfect place to stay in Cape Elizabeth! Such a bonus that it’s dog-friendly, too. Scroll the reviews and you’ll see that everyone who stays here loves it! Thanks Ilya, and we hope to return someday. 😊

Top Guest favourite

Apartment in Portland

5 out of 5 average rating, 69 reviews

Luxe Eco Studio near Back Cove

AmyRating, 5 stars1 week 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!

Top Guest favourite

Apartment in East End

4.96 out of 5 average rating, 134 reviews

The Howard on Munjoy Hill

KarenRating, 5 stars2 days ago

The location can't be beat, from walking to the waterfront to popping into restaurants to an engaging stroll to the art museum. Even though the apartment is in the city, the neighborhood was quiet and peaceful. I appreciated how updated and clean the apartment was without sacrificing the charm of an older dwelling. Would definitely stay there again!

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Quick stats about holiday rentals in Portland

Total rentals
1.6K properties
Total number of reviews
172K reviews
Family-friendly rentals
850 properties are a good fit for families
Pet-friendly rentals
450 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
800 properties have a dedicated workspace

Holiday houses in Portland

Top-rated holiday rentals in Portland

Holiday rentals for every style

Popular amenities for Portland holiday rentals

Stay near Portland's top sights

Other great holiday rentals in Portland

Quick stats about holiday rentals in Portland

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Destinations to explore