Maine

11 Stunning Airbnbs in Portland, Maine

by Sarah Lamagna
Updated October 02, 2021

Stunning AirBnBs To Get the Best Out of Portland, Maine
Photo: Noel V. Baebler / Shutterstock

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Aaahhh, Portland. Where the lobster rolls are served fresh and the soft, chocolatey whoopie pies are overflowing.

The capitol of Maine might be Augusta, but insiders know Portland is where it’s at. Just an hour north of Boston, Portland has the same amenities as Boston without the aggressive driving or strong accents. The Portland locals are some of the kindest and friendliest ones you’ll ever meet. Just remember that Mainers fiercely love their state and the businesses that operate there, so make sure to buy local whenever you can while you visit (especially for food!)

As visitors to Maine, you should know to always take off your boots when entering a home  – it’s just what they do. (Don’t have boots? Head to LLBean for their quintessential Bean Boots.)

Whether you’re in Maine shopping in Freeport (it’s only 20 minutes north) or touring the state’s lighthouses and beaches, the airbnbs in Portland will probably be a highlight of your trip. From luxurious downtown lofts to renovated barns, this bustling seaside town is an ideal spot for a lovely retreat. And the airbnbs in Portland below are the best of the best.

Related read: Guide to Lincolnville, Maine: Things to Do, Where to Eat & Stay

1. A Cape in a Cove

A cape in a cove Portland Maine

Why you should stay: Work out the kinks in your back with your own massage table in the en suite.

  • Sleeps: 4+
  • Minimum stay: 2 nights
  • Rates from: $245/night

Look no further than this Back Cove cape-style rental for unbeatable quaintness and solitude within the city limits. The house is filled with New England charm, shown through overflowing bookshelves, free-standing globes, and even a bongo drum set. But the real stunner to this place is the backyard.

Sip your morning coffee on the bistro-style table and chairs or lounge in the hammock before everyone else wakes up. For lunch, grab some local lobster and crack ‘em open on your picnic table out back. When the sun sets, grab some vino and wind down around the fire pit. Then sooth your achy feet in the hot tub before bed.

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Related read: 11 Amazing Maine Swimming Holes & Swimming Beaches

2. Renovated Barn

Renovated barn Portland Maine

Why you should stay: boots? How about high heels, ’cause this barn elegance oozes from every surface.

  • Sleeps: 2
  • Minimum stay: 3 nights
  • Rates from: $157/night

If you’re prone to Hay Fever, well…you’re in luck. There’s no hay left in this renovated, turn-of-the-century barn airbnb in Portland. Spoiler, though: the largest suite is in the former hayloft on the second floor. But if you find yourself sneezing while snoozing, it’s probably just because it’s allergy season.

Regardless of your allergy status, you’re sure to find it easy to relax here. There’s even a quaint reading nook complete with Victorian-era velvet chair with plenty of books on the side table. One last note: don’t muck up the place. This might’ve once been a barn, but the hosts have turned it into an incredibly modern, elegant space. No pigsties allowed.

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3. Romantic West End Gem

Romantic West End gem Portland maine
Photo: Airbnb

Why you should stay: You can’t tell if it’s a Portland airbnb or a secret garden in the English countryside.

  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $128/night

Travelers get to experience the beauty behind this hidden retreat in Portland’s West End neighborhood, starting with the Wisteria curtains adorning the courtyard’s brick walls. Not to nerd out, but you’ll feel like Elizabeth Bennet in “Pride and Prejudice” waiting for her Mr. Darcy – or at the very least, you may find yourself talking in an English accent.

If you’re feeling royal, take your Earl Grey tea out onto the courtyard. When breakfast is finished, put on your favorite bonnet and head into town for some grand shopping. Ladies can head to Bliss to find the best women’s coastal clothing while gents get their suit tailored at David Wood Haberdashery (it’s not just hats!)

Need evening plans? Order some traditional European dishes at Little Giant before going for a promenade on an actual promenade. With a stay at this Portland airbnb, you can expect to be saying “cheerio!” and “isn’t it grand?” to everyone you meet.

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4. Munjoy Hill Flat

Munjoy Hill Flat Portland Maine
Photo: Airbnb

Why you should stay: Be the first to see the sun rise in Portland.

  • Sleeps: 2
  • Minimum stay: 2 nights
  • Rates from: $212/night

Portland has various neighborhoods with varying degrees of uniqueness, but its East End is known for its quirky and funky side. The Munjoy Hill Flat is no exception, with unique furnishings and mid-century modern decor. If you’ve got some musical talent, take a stab at playing the mini grand piano. If cooking is more your style, then the large kitchen with ample counter space will suit your needs. Regardless of your skills and talents, be sure to take in the beautiful views from this amazing airbnb in Portland.

“We loved the view of the harbor from the window, especially when using binoculars provided by the host!”

Alisha, Rockville, MD
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5. The Cornelia

Photo: Airbnb

Why you should stay: Why have walls when you could have windows?

  • Sleeps: 4
  • Minimum stay: 3 nights
  • Rates from: $500/night

Can’t afford a ritzy apartment in New York City? Then look no further than this high-end penthouse in the heart of Portland (you know, the other NYC) without worrying about crowded subways or chaotic cab drivers. Not only does this place exude luxury (it’s a Portland airbnb in a top-floor penthouse, after all), but it also creates a welcoming ambiance for unwinding after being active all day. After popping into the first-floor ice cream shop, take your cone up to the rooftop deck and watch the yachts in the harbor.

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6. Peaks Island Cottage

Photo: Airbnb

Why you should stay: Listen to the crashing waves below from your private rooftop deck.

  • Sleeps: 12
  • Minimum stay: 2+ nights
  • Rates from: $686/night

Enter into your very own seaside getaway with this gorgeous cottage on Casco Bay. It’s chock-full of nautical elements including a porthole window in the largest bedroom. But you won’t need that circular window to get a glimpse of the surrounding vistas due to the sliding glass door leading to a private balcony. For a closer look at the ocean (though you can’t get that much closer), walk across the street to the pebbly beach.

Don’t forget to check the ferry times before checking in. You can find them here. Conveniently, the ferry departs Portland every hour starting early in the morning. It’s one of the pricier airbnbs in Portland, but you can split the cost as long as some guests don’t mind bunking on air mattresses.

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Follow ’em: @selkiesrest

7. Historic Downtown Home

Historic downtown home Portland maine
Photo: Airbnb

Why you should stay: Chic, affordable stay for a girls’ trip.

  • Sleeps: 5
  • Minimum stay: 2 nights
  • Rates from: $146/night

The bones of this house might be 177 years old, but everything else feels as modern as Carrie Bradshaw roaming the NYC streets in the latest designer dress. If you’re more of a Charlotte (she’s the refined one), get your favorite glass of chardonnay and lounge on the white leather sofa.

If you’re a Miranda, you’ll love that the home has fast Wi-Fi and plenty of space to work and read. And if you’re a Samantha (the over-the-top outgoing one), you’ll love that you’re just minutes from bars and restaurants so you’ll never have to go without brunch. The price here varies a ton month-to-month, so consider visiting midweek in the off-season (i.e. not summer) for the best deals.

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8. Three-story Deering Townhome

Three-story Deering townhome Portland Maine
Photo: Airbnb

Why you should stay: Close enough to the city to be convenient, but far enough away for plenty of quiet nights.

  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $251/night

Looking like it’s been plucked out of New England Home Magazine, this quaint townhome has everything you need for a comfortable week in Maine. Quaint feature reviewers loved include a white-picket fence and the manicured front garden, plus the muted colors and zen-like ambiance inside. When you want to venture out, check out the Treehouse Café or the Honey Exchange, both just down the road from this conveniently placed Portland airbnb.

“Bars, coffee shops and markets all walking distance and a gorgeous outdoor deck area for coffee and enjoyment.”

Jaime, Boston, MA
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9. Modern Rustic Downtown Condo

Photo: Airbnb

Why you should stay: Lux downtown condo with a to-die-to-for outdoor living space.

  • Sleeps: 4
  • Minimum stay: 4 nights
  • Rates from: $450/night

Airbnbs in Portland aren’t as tiny as those in bigger cities, but still, 1,600 square feet is a lot of space. But that’s what you get with this elegant rental. Have a small, high-end dinner party with your fellow travelers using the in-house decanter and wine cart (wine not provided, sadly.) You can sit at your bar counter or gather around the table before enjoying a few late-night drinks on the comfortable outdoor couches.

Couple traveling together? Enjoy your glass of wine in the soaking tub, complete with a wood-plank shelf (which is also a great place to prop up your iPad and watch a movie for a lazy evening in.)

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10. East End Loft

East End loft Portland Maine
Photo: Airbnb

Why you should stay: Location, location, location (and a stylish apartment.)

  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $275/night

Chesterfields are back in fashion and this downtown apartment makes a green one its focal point. With its emerald-green leather, you can’t help but think it looks like it’d be more at home in a funky cocktail bar (or perhaps the Emerald City?) This Portland airbnb place is so cute, even the Great and powerful Wizard of Oz may have a hard time dreaming up something more appealing.

What else could you want? A loaded bookshelf? Got it. Loft space for extra guests? Yup. What about a large rain shower? You already know the answer. The only thing you’ll need to wish for is a fun adventure, but you don’t have to be a wizard to find that.

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11. Francis Fassett House

Photo: Airbnb

Why you should stay: Stay at a historical landmark without paying admission to a museum.

  • Sleeps: 8
  • Minimum stay: 2 nights
  • Rates from: $267/night

Want to feel royal while visiting a New England seaside town? Look no further than the Francis Fassett House. Its namesake was one of Portland’s finest 19th-century architects. With almost 4,000 square feet of living space, even the largest families won’t be tripping over each other.

There’s plenty of place to relax in this roomy Portland airbnb. The green sitting room is perfect for your morning tea and a good book and the parlor room is ideal for playing a game of cards and sipping your whiskey. More of a chef? Make use of the grand kitchen. The home is a townhouse, but there’s a good chance it’s bigger than 90 percent of single-family homes in most other towns.

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Plan your trip to Portland, Maine

Portland has something for everybody in its bustling downtown. Check out these must-see recommendations!

  • If you’re not already staying on Peaks Island, take a trip on the Casco Bay ferry. Rent a golf cart while you’re there for easy traveling.
  • While you’re on Peaks Island, go to the Umbrella Cover Museum – it’s exactly what you think it is.
  • Grab a handmade handbag from Rough & Tumble for all you fashionistas out there!
  • Do a culinary tour of Old Port because you can’t just choose one restaurant to go to.
  • Take the Allagash Brewery tour and stop wondering why Mainers love the craft brew. Or take a Local Pour Tour and sample many Maine breweries.
  • Try the famous fries at Duckfat Friteshack. Seriously, don’t ask. Just do it.
  • Decipher how to get into Lincoln’s It’s not hard but I’m also not going to give it away.
  • And, of course, EAT LOBSTER. If you haven’t tasted fresh lobster (like from the boat!), then you haven’t lived. You can try Porthole or Bob’s Clam Hut first but you will want to sample all around town!

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