Portland Maine

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Top-rated vacation rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Charming Arts District Studio with Parking
Entire loft · 2 guests · 1 bed · 1 bath

Charming Arts District Studio with Parking2021 City of Portland registration STHR 000854 Enjoy the quieter end of Oak Street in the heart of Portland's Arts District. This studio is perfect for couples, solo adventurers and business travelers. Walk to just about everything! Travel restrictions may apply- please be sure to check the requirements for your state on the Maine government website.

Artsy Getaway - 2nd Floor Private Apartment
Entire apartment · 2 guests · 1 bed · 1 bath

Artsy Getaway - 2nd Floor Private ApartmentA large, sunny one bedroom apartment on the second floor with private entrance and parking in driveway. Lots of art on the walls, large comfy couch and fun open plan kitchen. Fifteen minutes to downtown Portland close to the highway for exploring beaches, breweries and local restaurants.

Oceanfront with amazing views and private entrance
Private room · 2 guests · 1 bed · 1 private bath

Oceanfront with amazing views and private entranceAs of May 1, all guests are welcome to book. Maine Covid-19 restrictions have been lifted, but we still encourage all guests to be fully vaccinated or be tested for Covid within 72 hours of arrival.

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Popular amenities for Portland vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Portland

  1. Entire house
  2. Portland
Quiet Comfy Victorian Escape
$182 per night
  1. Entire guest suite
  2. Portland
Garden Suite - A Peaceful Oasis on Munjoy Hill
$76 per night
  1. Entire apartment
  2. Portland
Private Garden Retreat on Munjoy Hill
$142 per night
  1. Private room
  2. Portland
Large, spacious, and eclectic Room, Private Bath
$70 per night
  1. Barn
  2. Portland
Garrison Cove Studio
$161 per night
  1. Entire cottage
  2. Falmouth
Osprey Cottage
$348 per night
  1. Entire cottage
  2. Portland
Cozy & Quiet Modern Cottage
$132 per night
  1. Entire guesthouse
  2. Portland
Portland's Heart
$300 per night
  1. Entire cottage
  2. Portland
Cottage hideaway, close to everything
$191 per night
  1. Private room
  2. Chebeague Island
Peaceful island retreat, walk to beach
$250 per night
  1. Private room
  2. South Portland
Bright clean room for one in fragrance free home!
$50 per night
  1. Entire house
  2. Portland
Back yard paradise
$459 per night

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.

How do I get around Portland?

Fly into Portland International Jetport (PWM), located about 15 minutes from downtown. You can explore this walkable city on foot — particularly the Arts District and Old Port, which are next to each other. The Greater Portland Metro operates several bus lines that navigate the city, and taxis and rideshares are also easily found. Renting a car is a good idea if you plan to explore nearby towns and attractions, such as the Portland Head Light.

When is the best time to book a Portland vacation rental?

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.

What are the 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.

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