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Price $10 - $1000+

539 Portland Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Portland holiday rentals from 4 rental sites including HomeAway, Booking.com, TripAdvisor, and more, ranging from $29 to $2150 a night. 
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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 a vacation rental in Portland? Tripping.com has 572 rental homes available in Portland. Potential renters will find 3 studios, 308 1-bedroom, 78 2-bedroom and 183 rentals with 3 or more bedrooms ranging from $29 a night to $2150 a night. Many of these properties are instantly bookable.

    The average price of a nightly rental in Portland is $253 while the average price of a weekly rental is $2121. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Portland home is $7497.

    Wondering if you can bring your favorite dog or cat with you? We have 104 pet friendly vacation rentals available for you. In addition to accommodating pets, Portland rentals offer a variety of amenities. In particular, 260 rentals have internet and wifi, 480 have TV and/or cable and 30 have a pool or hot tub.

    Search properties from 4 rental sites in Portland where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 263 HomeAway rentals, 237 Booking.com short term rentals and 39 TripAdvisor vacation rentals.