327 Portland Holiday Rentals

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Information about Portland

About Portland

Perched on Casco Bay, it’s Maine’s largest urban area and is home to a plethora of island and coastal communities. The bustling seaport city is known as a cultural, dining, and shopping haven, as well as a mecca of hiking and biking trails, coastal beach spots, and scenic routes that’ll keep travelers of all sorts busy for sure. The more than scenic town is a year-round destination offering picturesque cobblestone streets, plenty of art galleries, a load of fresh seafood restaurants, and tons of history, especially at the Old Port waterfront, where you’ll find working fishing wharves and converted vintage warehouses now boasting retail shops and restaurants. Sitting atop a bluff nearby is also the Western Promenade, a public park boasting river and mountain views. There’s even the surrounding district of West End, which is full of Victorian-era homes, including the Victoria Mansion museum.

Get a taste of Maine state history by embarking on a self-guided walking tour of Portland's four major historic districts. The once-fishing-only town has risen to the top of hip travelers' must-visit lists over the last several years, has garnered acclaim as a top food destination, and is packed with funky boutiques, trendy bars, and lots of fun things to do.

Things to do in Portland

All year round, there’s plenty to take advantage of in Portland. Fight the summer heat with a dip into the refreshing waters, or watch the leaves slowly fade from vibrant green to lovely shades of yellow, red, and orange in the autumn time while visiting a nearby apple orchard for a day of apple-picking and eating cider donuts. Snow bunnies will adore ice-skating around the city’s many local rinks, or cross-country skiing through nearby pine forests in the winter-- as well as making their way through the countless cafes spread across the creative West End hub.

For something different try taking the scenic route on the mail boat, a charming three-hour ride through the Casco Bay that allows for the chance to see Great Diamond, Little Diamond, and the Cliff islands. Or catch a baseball game at Hadlock Field, home of the Portland Sea Dogs before taking a stroll through the Portland Museum of Art, which houses works by Edward Hopper, Picasso, Matisse, and even Monet.

Portland Day Trips

Explore the Pine Tree state through its finest urban peninsula all in a day. For most visitors, a ride on the Luck Catch through Casco Bay is a must. The boat takes a dozen or so passengers on a ninety-minute tour to learn about how lobster traps are hauled, set, and baited. You can even participate in the lobster catching process yourself!

Another entertaining way to learn about Portland's history, architecture, and major sites would be to climb on board the Portland Discovery trolley tour, which is a 105-minute-long fully narrated trip that even makes a pit stop at the famed Portland Head Light for a photo op. Art lovers will also no doubt enjoy taking a tour of the historic Winslow Homer Studio. Tours start at the Portland Museum of Art and you’ll get the chance to witness the spot where the famed American artist lived and painted many of his greatest masterpieces until his death in 1910.

Portland Accommodations

From hotels and motels, to charming inns and guest lodges, you’ll find a wide variety of accommodation options in Portland. There’s the Holiday Inn by the Bay, with an enviable waterfront location that makes it a super popular choice for travelers. Luxury seekers can opt for the Westin Harborview, which was recently-renovated in January 2014 to much fanfare. It’s ideally located in the heart of downtown Portland, and even has a trendy rooftop lounge offering tasty cocktails and 360-degree views of the city.

For something more quaint, try out the Pomegranate Inn, a charming stay in the West End that was built back in 1884. The Italianate home is brimming to the tee with funky antiques and colorful contemporary art. There’s even a carriage house to shack up in. Rad.

Portland Transportation

It’s easy to get around, especially via METRO bus service, which offers rides throughout the Greater Portland region while making convenient stops within walking distance of museums, galleries, shops, restaurants, and historic landmarks. Travelers also have the option to connect to train, ferry, and other regional transportation options. There’s even expanded bus service to Yarmouth and Freeport, as well as more comfortable options with Concord Trailways, a coach line that serves points in New Hampshire and Maine to Boston South Station and Boston’s Logan International Airport.

The local Downeaster also makes daily round-trips between Brunswick, Maine and Boston. And if you’re flying in, Portland International Jetport, Maine’s largest airport, is a compact and close spot just five miles from the heart of Portland. Water lovers might even opt for the Casco Bay Ferry, which can carry passengers, vehicles, and freights between Portland, Maine and the islands of Peaks, Little Diamond, Great Diamond, Long Island, Chebeague, and Cliff. Scenic summertime music cruises, private charters, and lobster bakes are also available. Go on and explore the coast of Maine.

Vacation Rentals in Portland

Looking for the perfect vacation rental for your Portland getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Portland offers 327 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 265 properties with high-speed internet, 51 full with jacuzzi and pool, and homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $17994 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Portland has 327 gorgeous homes with 99 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

Search properties from 6 rental sites in Portland where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 204 HomeAway rentals, 46 Booking.com short term rentals and 36 TripAdvisor vacation rentals.