
Vacation rentals in Portland
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Popular amenities for Portland vacation rentals
Private vacation rentals in Portland

Sweet Fern Cabin on Merrymeeting Bay

East End, Munjoy Hill ~ light filled retreat

Bright & Sunny Apartment with Patio

Luxury Year-round Treehouse with private hot tub

Spacious, relaxing, Back Cove 3 bed

Portland 1 Bedroom Condo in the Arts District.

Port City Studio Loft

Quiet West End Retreat - parking - 100% Non Smoker
House rentals in Portland

The East End

Waterfront Gem walkable to Restaurants!

2 bed house w/king bed, pets & off-street parking!

East End Unit

LUX Designer Private Waterfront

Beautiful Coastal Maine Getaway

New build with hot tub in Old Orchard Beach

Unplug at a Beachy Bolthole with Classic New England Style
Condo rentals in Portland

Luxury Beach Front Condo! Prime Location!

First Floor Portland Condo 3 Bed 2 Bath + Parking

Modern Industrial Beach Cottage

Cozy condo by the beach!

Heart of city, water view, off street parking

Comfy condo with loft by the beach!

Mary J. Eastburn House--Baxter Suite

Luxury Condo in Downtown Portland Old Port
Quick stats about vacation 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
Your guide to Portland
All About Portland
Perched along the dramatic slate-gray waters of the Atlantic Ocean, where gulls wheel and whitecaps dot the surf, Portland is quintessential Maine combined with the allures of a metropolis. Established as a booming port town by traders and fishermen, Portland is now the state’s biggest city. Here you can tread cobblestone streets, visit historic lighthouses, and dine on lobsters hauled from the nearby waters. But you’ll also find top-notch museums and galleries, boutique shopping, and a celebrated foodie scene that boasts award-winning restaurants and a thriving microbrew culture. New and old Maine commingle comfortably here, where you can enjoy the best of both worlds.
The best time to stay in a vacation rental in Portland
Summers are brief and mild in Portland, where June through September bring average temperatures in the 70s Fahrenheit. October and November cool down, with temperatures in the 40s and 50s, and December through February are chilly, with temperatures in the 30s. Things grow steadily warmer starting in March, ushering in 40-degree weather and climbing into the low 60s by May. You’re likely to encounter rainfall year-round, and snow December through March. Pack lots of warm layers, hats, and scarves.
Top things to do in Portland
Portland Head Light
The Portland area is home to several historic lighthouses, but the Portland Head lighthouse is the undisputed heavyweight. Construction began in 1790, making it the oldest in the state. Visitors can tour the quaint lighthouse and its grounds, which include the former keepers’ house, now repurposed as a museum. Take in the sweeping vista, which includes views of four more lighthouses and the possibility of watching lobstermen pulling their traps from the bay, before taking a scenic stroll through Fort Williams, the 90-acre park in which the lighthouse resides.
Casco Bay and the Calendar Islands
Hop on a ferry (or charter a water taxi) to tour the photogenic Calendar Islands, clustered in grand Casco Bay. You can experience small-town Maine life here. Teensy Cliff Island has fewer than 60 year-round residents and a small schoolhouse. Peaks Island offers four miles of uninterrupted coastline and historical sites such as a World War II artillery bunker. Tonier Great Diamond Island, where a private community has been installed within the refurbished military buildings of historic Fort McKinley, boasts upscale dining. Don’t have time to set ashore? Casco Bay Lines, the island ferry service, offers speciality cruises that will afford you a sailor’s-eye view of the islands and dazzling bay.
Old Port District
Travel back in time in this quaint maritime neighborhood that still looks very much the way it did in the early 19th century. Narrow cobblestone streets and historic brick warehouses lend the enclave its cozy feel, but that’s where the frozen-in-time vibe ends. The restored Old Port District, which is on the National Register of Historic Places, is home to quirky boutiques, inventive eateries, and brewpubs. You’ll find many of these offerings on buzzy Exchange Street.
Frequently Asked Questions
How is the weather in Portland?
Portland experiences a humid continental climate. Summers are typically warm, averaging 79°F (26°C), while winters, known for their snowfall, can drop to 12°F (-11°C). Autumn is colorful with fall foliage, and spring brings mild and refreshing weather.
What are some of the best things to do in Portland?
There's a wealth of activities to enjoy in Portland. Visitors often explore the historic Old Port district, sample local produce at the Portland Farmers' Market, or take a Casco Bay Lines Ferry to the nearby islands. Visiting the Portland Museum of Art is also frequently recommended.
What is the best time of year to visit Portland?
The most popular time to visit Portland is during the summer, from June to August. This period features warm weather and several local events, including the Old Port Festival in June and the Maine Lobster Festival in nearby Rockland in August.
What are the best places to stay in Portland?
Portland, Maine, has numerous charming neighborhoods, each with a unique character. The Arts District is known for its creative buzz and art galleries, while the Old Port area boasts cobblestone streets and waterfront views. Peaks Island, just a 20-minute ferry ride from downtown, provides a serene, coastal stay.
What are the best places to visit in Portland?
Visitors to Portland often find delight in exploring the Portland Museum of Art, the historic Victoria Mansion, and the Eastern Promenade park. A trip to the iconic Portland Head Light, one of the oldest functioning lighthouses in the US, is also frequently suggested.
What are some hiking trails in Portland?
For nature enthusiasts, Portland has several hiking trails. The Fore River Sanctuary Trail provides picturesque views and a chance to spot local wildlife, while the Back Cove Trail offers an easy urban hike around a tidal basin. The Peaks Island Loop is another scenic coastal trail.
What are some family activities to do in Portland?
Families visiting Portland can enjoy a fun-filled day at the Children's Museum and Theatre of Maine, explore the fascinating sea life at the Maine State Aquarium, or take a scenic ferry ride to Peaks Island. A stroll in the Eastern Promenade park is also a popular choice.
What are some of the best day trip ideas in Portland?
From Portland, visitors often take day trips to the coastal town of Kennebunkport, the scenic Peaks Island, or Freeport for shopping at the famed L.L. Bean flagship store. The stunning Acadia National Park, though a bit farther at 160 km, is a popular choice for a longer day trip.
What types of vacation rentals are available in Portland?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Portland. From over 100 condo rentals to over 430 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Portland?
Yes! Work meets play with ease at over 800 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
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- Pemaquid Beach
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- Dunegrass Golf Club
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