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Portland, Maine, is one of the top getaways in New England and one of the best stops on a New England coastline road trip. So I’ve rounded up the best Airbnbs in Portland, Maine.
The Ultimate Portland, Maine Travel Guide
From Colonial homes to coastal cottages to penthouse apartments, these are the perfect “home bases” for exploring Portland’s harbors, islands, parks, attractions, and historic city center.
Here are the best Airbnbs in Portland, Maine to inspire your next trip!
Ocean Views
6 guests bedrooms beds.5 baths
Get ready to fall in love with the ocean views from almost every room in this home. You’ll have a gourmet kitchen, fireplace, garden, hot tub, indoor jacuzzi, four decks and porches, a clawfoot tub, and a luxury glass shower.
Art-Filled Home
6 guests bedrooms beds baths
This exquisitely decorated, art-filled home in Portland’s sought-after East End neighborhood has water views from the master bedroom and roof deck. There’s also a stunning kitchen, beautiful decor and furniture in every room, a large dining room, and a fabulous patio with outdoor seating.
East End Apartment
4 guests bedroom beds1 bath
Get ready to fall in love with this sunny, loft-style apartment close to the Eastern Promenade and some of the city’s best restaurants and breweries. This apartment has a green Chesterfield couch, colorful artwork, mid-century modern furntiure, and a cozy loft mezzanine bedroom.
Romantic Retreat
2 guests bedroom bed1 bath
You’ll love this island cottage that’s on a sandy beach with water views from every window. This home has a fenced-in yard for your furry friends, a golf cart for exploring the island, unique furniture, and al fresco dining. Plus, you’ll be close to a public boat ramp, the ferry terminal, restaurants, and shops.
The Penthouse of Your Dreams
4 guests bedrooms beds baths
This dreamy penthouse is in the heart of the Old Port neighborhood, and you’ll love the private patio and incredible views. The apartment is an architectural marvel that’s perfect for a girls’ or couples’ getaway. You’ll be close to public transportation, parks, nightlife, restaurants, bars, and shops.
Room For Your Whole Crew
14 guests bedrooms beds baths
Get your whole crew together to enjoy this craftsman-style home with water views. You’ll have two kitchens, three living rooms, a gas fireplace, lots of on-site parking, a screened-in porch, patio, hot tub, and large yard. Plus, you’ll be close to Portland’s Old Port.
Modern Condo
4 guests2 bedrooms beds bath
If you want a budget accommodation that’s centrally located, then this modern condo is for you. This first-floor unit has a stunning kitchen, breakfast bar, and a private patio. Plus, you’ll be able to walk to many of the city’s best attractions, restaurants, and shops.
Recommended Tours in Portland
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What are your favorite Airbnbs in Portland, Maine? Share with us in the comments!
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The Best Airbnbs in Portland, Maine
Frequently Asked Questions
Is it worth visiting Portland, Maine?
Yes! After just one visit, Portland is one of my favorite cities in the Northeast United States! There are so many public parks and outdoor spaces, I felt very safe as a female traveler, and the city’s food and beer scenes are fantastic.
What is the best month to visit Maine?
June – August is Portland’s peak tourism season. These are the driest months of the year, and daytime temperatures rarely go above the high 70s. It’ll be in the 50s at night, so bring layers. Summer is also when most of the city’s festivals, art exhibits, and regattas take place. Tourist numbers and hotel prices will be at their highest during these months, so book your tours and accommodation in advance to save some money and ensure availability.
Portland is the perfect place to visit in September – November if you want to avoid the crowds and peep some Fall foliage. Two of the city’s renowned foodie events – Harvest on the Harbor and Portland Beer Week – are held during these months. Temperatures will drop to the 50s in the day and 30s at night, and these are the rainiest months of the year. Vacation home rentals and hotels lower their prices significantly in these months, but some activities and boat tours don’t operate in the Fall.
December – February is Portland’s off-season because daytime temperatures are below freezing, and it’s in the low teens at night. Snow is common, and the city hosts some incredible snow activities, such as ice fishing, cross-country skiing, ice skating, and sledding. Many tours, attractions, and restaurants close or reduce their hours during the winter. If you can brave the cold, then you can score some great accommodation deals.
March – May is Portland’s shoulder season. It won’t start feeling like Spring until May when daytime temperatures will finally reach the high 60s. Rain is common in these months, so bring rain gear and warm clothes. The rain will bring beautiful Spring flowers to the city and surrounding area. Mid-April is the start of the whale-watching season, so boat tours will resume. Tourist numbers and prices will also still be relatively low during these months.
Is Portland, Maine walkable?
Portland, Maine, is a very walkable city. Some of the neighborhoods are too far apart to walk between them, and the beaches are further from the city, but public transportation and rideshares are easy to find and use.
How long should you spend in Portland?
Give yourself at least 3-4 days to explore Portland. This will give you plenty of time to experience the historic downtown, enjoy the food scene, and take a day trip.
What is there to do in Portland, Maine for 2 days?
If you only have two days in Portland, then prioritize these activities:
1. Visit the Portland Head Light
2. Go on a schooner cruise
3. Explore the Old Port
4. Have a picnic at the Eastern Promenade
5. Visit the Portland Observatory
6. Do a craft brewery tour
7. Spend a day at Willard Beach (if it’s warm enough)
8. Walk out to the Spring Point Ledge Lighthouse
9. Take a ferry to Peaks Island
10. Visit the Historic Victoria Mansion
11. Go on a food tour
What food is Portland, Maine known for?
The Best Restaurants in Portland, Maine:
My Favorites: Eventide Oyster Co. (Oyster Bar, $$$), Central Provisions (Small Plates, $$$), Fore Street Restaurant (New American, $$$$), Duckfat (Cafe, $$).
Fine Dining: Hugo’s (Farm-To-Table, $$$$), Grace (American, $$$$), The Corner Room Italian Kitchen & Bar (Italian, $$$).
Seafood: J’s Oyster ($$), The Highroller Lobster Co. ($$), Luke’s Lobster Portland Pier ($$).
Craft Beer: The Great Lost Bear (Gastropub, $$), The King’s Head (Pub, $$), Gritty McDuff’s Brew Pub (Brewpub, $$).
Brunch: Bayside American Cafe ($$), The Front Room ($$), The Sinful Kitchen ($$).
Waterfront Dining: Portland Lobster Company (Seafood, $$), DiMillo’s On The Water (Seafood, $$), Saltwater Grille (Seafood, $$$).
How many days do you need for Portland, Maine?
Give yourself at least 3-4 days to explore Portland. This will give you plenty of time to experience the historic downtown, enjoy the food scene, and take a day trip.
Is downtown Portland safe?
I felt very safe during my entire trip to Portland. But, as with any destination, you need to take precautions to keep yourself safe. Don’t walk by yourself at night, stay in a secure and well-located hotel or vacation home, use slash-proof, lockable, and RFID-protected bags and purses, and always have a charged cell phone with you.
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This article about the best Airbnbs in Portland, Maine, is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this post about the best Airbnbs in Portland, Maine, are affiliate links, and, at no cost to you, I may earn a small commission.
