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Portland vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Portland

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

Rental unit in East End
RETRO BnB in the Heart of East End Portland
Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!
$178 per night
Hotel room in West End
Skolfield Inn | Parking | Self-check-in | Garden 2
Welcome to The Skolfield Inn! ROOM 2: In this room you can relax on the couch with a book or snuggle up in bed to watch Netflix. While the room is bright and spacious, the bathroom is what keeps people coming back for more! With a double vanity, large marble glassed in shower, and original hardwood floors, you will look forward to your own little spa-like oasis. This room also comes with one, off street parking spot (cannot support larger SUVs/trucks).
$168 per night
Hotel room in Downtown Portland
Inn at Parkspring | Private entrance | Parking | 6
Location, Location, Location! Welcome to The Inn at Park Spring! Formerly the Park Spring Bed & Breakfast, we recently dropped the breakfast to serve Airbnb guests near and far as a boutique hotel. ROOM 6: With your own private guest entrance at the back of the building (motel style), this room offers a quiet retreat in the heart of Portland. One off street parking spot is offered, only one block away from the inn.
$181 per night

Stay near Portland's top sights

Portland Harbor Museum348 locals recommend
The Maine Mall86 locals recommend
Peaks Island176 locals recommend
DiMillo's On The Water101 locals recommend
Fort Williams Park229 locals recommend
Portland International Jetport50 locals recommend

Portland beach vacation rentals

Rental unit in East End
Ocean Way East End
$164 per night
Rental unit in East End
Parkside Retreat on Portland's Eastern Promenade
$172 per night
Rental unit in East End
Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom
$172 per night
Rental unit in West End
Huge Dreamy urban Artist-designed loft
$199 per night

Private Portland vacation rentals

Rental unit in Portland
Beautiful 1st Floor Apartment & Amazing Shower
$180 per night
Rental unit in Downtown Portland
Spacious Apartment Walkable to Downtown Portland
$148 per night
Loft in Downtown Portland
Spacious Studio in Arts District w/ Free Parking
$198 per night
Rental unit in West End
Charming & Sunny West End Nest with Parking
$179 per night

Portland house rentals

Home in South Portland
The Knightcap
$160 per night
Private room in Portland
The grey room - quiet and calming
$98 per night
Home in Portland
Quiet Comfy Victorian Escape
$210 per night
Home in Portland
Explore Portland from a 18th-Century Victorian
$183 per night

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.

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland