Find Vacation Rentals in Portland (ME)

Highlights Portland (ME)

  • New England
  • Civil war forts
  • Lobster and seafood
  • lighthouses
  • Museums

Best Vacation Rentals in Portland (ME)

Guests agree: these stays are highly rated for location, cleanliness, and more.
Portland (me), Cumberland County (maine)
Vacation Rental • 517 ft² • 4 Bedrooms
(20 reviews)
This studio suite can sleep 2 to 4 people, is newly built, with a complete kitchen, washer/dryer, air-conditioning, cable tv, internet, pull out sofa, designated parking spot for one car, BBQ area, miles of hiking trails across the street with saltwater marsh & waterfalls. Centrally located to downtown Portland, ferry service to the Islands, swimming, sailing and all of coastal Maine. Portland License # STHR-004156-2022
from $247 / night
Portland (me), Cumberland County (maine)
Vacation Rental • 1496 ft² • 3 Bedrooms
(53 reviews)
Third Floor home of a 2 residence home. 3 bedrooms include a master with CA King temperpedic bed, 2nd BR has a Queen size bed, and 3rd BR has a Full size bed. Kitchen includes granite counters and dishwasher. Brick exterior with easy parking in back of house. Owner occupied and is available to assist with questions you might have about the Greater Portland Area. Close to the Western Promenade park.
from $227 / night
Portland (me), Cumberland County (maine)
Vacation Rental • 8 Guests • 4 Bedrooms
(10 reviews)
Vacation summer house on Great Diamond Island, with the boat mooring right out front.Our 4 bedroom house sports a grand view of Casco Bay because of its proximity to the shoreline. The panoramic west view provides an unobstructed view of the sunset to the horizon every night. The wrap around front porch has a picnic table for outdoor eating and a hammock for relaxing. A propane bbq for outdoor cooking. There are two upper level balconies expanding two of the upstairs bedrooms. Perfect reading nooks. Beach access is quick and easy right down off the front yard. There is a rock reef just off ...
from $401 / night

Prices and availability

Vacation rental prices Portland (ME)

$257for 11 Feb - 18 Feb
$509 annual average
Average price per week

Vacation rentals availability Portland (ME)

52%for 11 Feb - 18 Feb
45% annual average
Percentage of available rentals

Vacation rentals in Portland

Experience Portland with a comfy vacation rental

Set on a peninsula in Maine’s Casco Bay, Maine is a quintessential slice of New England on the US Atlantic Coast. The town has all the trappings of a nostalgic coastal town where seagulls cry and the smell of fish & chips waft through the salty air. The Old Port district is quite reminiscent of an old European town thanks to its 19th century streets, bookstores, and intimate pubs. When you tire of all those historic landside distractions and museums, take off on a lobster-hunting excursion, a sunset cruise or a boat ride to the nearby islands. Maine’s largest city is best enjoyed with a vacation rental as your base.

Breezy vacation properties for all

A true four-season destination, Portland is easily accessible from Boston – it’s just a 2 hour drive up north. Vacation rentals in Portland are well-equipped with amenities such as high-speed Wi-Fi, television, sunny patios, and fully-functional kitchens. The best part is you can choose from a range of sea-facing rentals with divine Atlantic Ocean views. Families with kids and dogs, solo travelers, and honeymooners will feel right at home here. With regards to the best area to live in, the Old Port district in Downtown Maine is quite popular owing to its proximity to popular lobster houses, bars, and museums – it’s also right by the Casco Bay waterfront. The Arts District will appeal to museum-goers as Portland’s Museum of Art and the Children’s Museum are both located here. For cheaper prices on accommodation, look for vacation rentals around the Portland International Airport, and those off the highway.

Travelers and activities

A destination for museum fiends

Maine’s history has been wonderfully preserved through its historic parks, mansions, and lighthouses. Rent a car and set about exploring the coast. Hard to miss is the picturesque Portland Head Light which is America’s most photographed lighthouse having guided ancient mariners since 1791! While it is closed to the public, visitors can certainly enjoy views of the craggy coastline and working harbor from here. Nearby is the Fort Williams Park, a historic artillery base where you can stroll through the ruins and check out the WWII bunkers on the lawns. Food trucks at the park sell tasty lobster rolls. Finally, on a nice day consider kayaking out to Fort Gorges on Hog Island Ledge where you can explore the ruins of the former US military fort.

Museum-hopping can be just as fun!

Start at the Portland Museum of Art (PMA) opened in 1882 in the iconic Arts District. This is Maine’s oldest and largest public art institution, and it houses important European, American, and Contemporary art – look out for Renoir and Monet’s works, as well as those of local Maine artists. The Maine Jewish Museum in the East End district offers visitors a crash course in the contribution of Jewish immigrants to the region – there are art exhibitions to be enjoyed here as well. Finally, don’t miss the immersive and thoroughly engaging Children’s Museum & Theater where kids can milk fake cows, navigate replica lobster boats, and even try some dress-up theater! If possible, catch a show at Maddy’s Theater, America’s oldest continuously operating theater for children.

Travelers and activities

A destination for culture seekers

Fuel yourself with a hearty breakfast at Becky’s Diner, local favorite since 1991. Their luscious chocolate chip pancakes, pastrami omelets, and sausage patties are highly sought after and the prices are honest too. Bang on the pier is DiMillo's On The Water, a bit of a Portland institution, opened in 1954 by Tony DiMillo. Their Lobster Mac & Cheese, fried clams, and Angus beef preparations are excellent. Five minutes away is another heavyweight on the town’s culinary scene – the Portland Lobster Company. Enjoy their famous steamed lobster dinners, and mussels in romantic waterfront setting. A memorable meal in a lighthouse setting awaits at The Lobster Shack at Two Lights. Savor their classic warm clam chowder to the sounds of the crashing surf. What about drinks? Don't forget Portland’s brewery of choice since 1988, the award-winning Gritty’s Portland Brew Pub – you’ll love their classic pale ales and pub fare.

A booming performing arts scene

Portland boasts a fun line-up of events be it theater, cinema, or live music. With Moorish and Art Deco architectural elements, the historic State Theater is Portland’s top choice performing arts venue with a capacity of 1,870 spectators. Close on its heels is the Portland House Of Music and Events (H0ME) where some of the region’s best tribute bands perform – they have an expansive dance space too. Next is Portland’s original dive bar, the dimly lit Gino’s Rock Club which has welcomed both newbie bands and established ones over the years. If punk, metal, and mosh pits are your idea of a good time, hit Gino’s! Mellow things down a bit at Blue, a live music venue known for its jazz, bluegrass, and blues concerts. Looking to catch a movie with that someone special? Book tickets at the super comfy Nickelodeon Cinema.

Did you know that in 2009, Portland’s folks put together the world’s largest lobster roll at 61 feet using 48 pounds of lobster flesh?

Top 5 travel tips for Portland

1. Cruise Maine’s colorful coastline

One of the best ways to experience the famed New England coastline is with a Maine coastal cruise. Knowledgeable captains will regale you with tidbits of information on the islands, lighthouses, and historic districts of coastal towns you’ll cruise by!

2. Nature and art at Scarborough town

Fifteen minutes south of Portland lies the town of Scarborough whose top attraction is the Prouts Neck Cliff Walk – make sure to photograph the genteel old homes en route. You can also visit the erstwhile home of one of America’s greatest landscape artists, Winslow Homer.

3. A trip to Ferry Beach State Park

Set on the pristine Saco Bay, Ferry Beach State Park merits mention for its sweeping vistas of white sand beaches along the Saco River. Well-marked natural trails and guided programs are a fun and informative way to reconnect with nature.

4. Lobster hunting excursions

Having tried all those tasty lobsters at Maine’s coastal cafes, how about catching some of your own? A lobster cruise is a fantastic way to get acquainted with local lobster men and pick up some hunting skills.

5. Arcade fun at Palace Playland

Get in touch with your inner child at New England’s only beachfront amusement park where over 250 games await. Classic rides such as Tilt-a-Whirl, Dodgem Cars, and carousels make this a mandatory stop for the family.

FAQs: Vacation Rentals in Portland (ME)

How much do you pay, on average, for vacation rentals in Portland?

Our data shows that Portland had an average price of $462 per night, a relatively high one for a city in the USA.

Which months allow you to save the most on vacation rentals?

Those who want to save as much as possible visit Portland in February, March, or May, the cheapest months of the year, with average prices of $376, $409, and $416 per night, respectively, based on the previous year.

During which months are vacation rentals more expensive in Portland?

Following the data observed last year, costs per night for accommodation here are usually higher, on average, during the months of October ($548), November ($501), and June ($497).

Is it necessary to plan a trip to Portland well in advance?

So you don't run out of accommodation options in Portland, we recommend you to plan ahead as 87% of rentals are usually booked, according to last year's data.

What are the best months for a last-minute getaway?

Last year, the months with the largest number of accommodations available of the year in Portland were June, July and October, with average availabilities of 25%, 23%, and 18%, respectively.

How many rentals are there in Portland?

Holidu works with 3 different partners to offer you an inventory to choose between 60 properties we have in Portland.

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