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Popular Portland Vacation Rentals

Find the perfect Portland vacation rental

Apartment Portland
$172 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (67 ratings)
Portland, Cumberland County, Maine, United States
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Vrbo
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House Portland
$139 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (1 rating)
Portland, Cumberland County, Maine, United States
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Vrbo
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House Portland
$204 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
"Excellent" (132 ratings)
Portland, Cumberland County, Maine, United States
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Vrbo
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House Portland
$238 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (139 ratings)
Portland, Cumberland County, Maine, United States
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Vrbo
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House Portland
$256 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (57 ratings)
Portland, Cumberland County, Maine, United States
Details
Vrbo
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House Portland
$208 per night
House ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (47 ratings)
Portland, Cumberland County, Maine, United States
Details
Vrbo
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Apartment Portland
$139 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (85 ratings)
Portland, Cumberland County, Maine, United States
Details
Vrbo
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House Portland
$301 per night
House ∙ 5 guests ∙ 2 bedrooms
4.8
"Excellent" (10 ratings)
Portland, Cumberland County, Maine, United States
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Vrbo
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Apartment Portland
$170 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (82 ratings)
Portland, Cumberland County, Maine, United States
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Vrbo
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Apartments and vacation rentals with a kitchen

House Kitchen Portland
$110 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (58 ratings)
Portland, Cumberland County, Maine, United States
Kitchen
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Vrbo
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House Kitchen Portland
$253 per night
House ∙ 8 guests ∙ 3 bedrooms
4.5
"Outstanding" (48 ratings)
Portland, Cumberland County, Maine, United States
Kitchen
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Vrbo
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Apartment Kitchen Portland
$257 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (80 ratings)
Portland, Cumberland County, Maine, United States
Kitchen
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Vrbo
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Vacation rentals with Wi-Fi

Cottage Internet Portland
$343 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (58 ratings)
Portland, Cumberland County, Maine, United States
Internet
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Vrbo
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Cottage Internet Portland
$248 per night
Cottage ∙ 4 guests ∙ 3 bedrooms
4.9
"Excellent" (83 ratings)
Portland, Cumberland County, Maine, United States
Internet
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Vrbo
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Condo Internet Portland
$560 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (159 ratings)
Portland, Cumberland County, Maine, United States
Internet
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Vrbo
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Vacation rentals and apartments with air conditioning

Apartment Aircondition Portland
$202 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (130 ratings)
Portland, Cumberland County, Maine, United States
Aircondition
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Vrbo
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House Aircondition Portland
$483 per night
House ∙ 4 guests ∙ 3 bedrooms
4.9
"Excellent" (89 ratings)
Portland, Cumberland County, Maine, United States
Aircondition
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Vrbo
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Condo Aircondition Portland
$525 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (222 ratings)
Portland, Cumberland County, Maine, United States
Aircondition
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Vrbo
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Frequently Asked Questions

Is renting a vacation home in Portland expensive?

In Portland, vacation rentals start at $108 per night.

Can I book a vacation rental in Portland?

Tripping.com offers great selection on vacation rentals with 1,006 offers currently available in Portland.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Portland Information

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.

Popular Day Trips Near Portland

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