Destination guide

Experience Portland from vacation home rentals

History and culture come together winningly in Portland, one of the heritage jewels of Maine. The city’s graceful waterfront, quaint old port, and charming downtown are magnets for lovers of architecture, while the arts district comprises many important museums and galleries. From the rugged beauty of Casco Bay to the buzz of Monument Square, Portland provides the perfect recipe for a spontaneous short break. If you're planning to get to know this hospitable city a little better, Portland vacation rentals are a great way to absorb new experiences without forgoing the comforts of home.


Historic sites near vacation homes in Portland

Portland has a rich history that’s displayed through many heritage sites. Vacation rentals can be found near places like Victoria Mansion, a 19th-century Italian villa with an ornate interior and museum, and the Portland Observatory, a historic maritime signal tower and museum. You could also visit Bug Light, a historic lighthouse inspired by a Greek monument with spectacular harbor views.

Things to do

Sightseeing near Portland vacation rentals

Portland Head Light is one of the city’s most iconic landmarks. The 1791 lighthouse was the first to be built in the state of Maine, and still shines its beam over the entrance to Portland Harbor. Its fame was further enhanced when Edward Hopper made it the subject of one of his best-known paintings. The former lighthouse keeper’s cottage is now a museum, where you can learn more about the historic structure and how it has kept pace with technological changes. The complex is situated within Fort Williams Park, an military site that played a vital role during both World Wars.


Things to do near Portland vacation homes

A walking tour of the Old Port district is one of the highlights of any first-time visit to Portland. This quaint quarter of cobblestone streets and fishing piers was once the commercial hub of the Portland peninsula. The disused buildings were saved from demolition in the 1970s and converted into desirable living and working spaces. Today, the Old Port pulses with life day and night, with a wealth of restaurants and bars, fashion boutiques, street entertainment, and cultural events. The annual Old Port Festival is a red-letter day, offering family-friendly activities, local food specialties, and live music.


Local weather for your stay in Portland vacation homes

The climate of Portland falls within the range of humid continental, resulting in cold, snowy winters and warm, moderately wet summers. Thanks to its location on the Gulf of Maine, summer humidity is moderated by the cool waters of the Atlantic Ocean. In high summer, it’s a good idea to look for Portland vacation rentals with a pool or close to the beaches of Casco Bay, to provide welcome refreshment at the end of an action-packed day. A good tip for finding bargains in Portland vacation rentals is to visit during spring or fall, when temperatures are ideal for sightseeing.

Natural features

Marine life in Portland

Casco Bay’s fishing heritage lives on in its abundant marine life. Predominant species include mackerel, bluefish, and striped bass, along with crustaceans such as mussels, clams, and the tasty lobsters that are a specialty of Maine restaurants. Fishing trips can be booked within easy reach of downtown Portland vacation rentals, with the likelihood of bringing home a freshly caught supper. Native and migrating sea birds also benefit from the protective bay, most commonly cormorants, gulls, and ducks. Rare sightings of ospreys, eagles, and herons are a bonus for keen bird-watchers.

How to get there

Transportation options to and around Portland

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 2.6 mi (4.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Brunswick, ME (NHZ-Brunswick Executive), which is 23.2 mi (37.3 km) away.

If you'd rather travel by train, the main station serving the city is Portland Transportation Center.

Good for couples

Couple's retreat near Portland vacation homes

Portland’s scenery and quirky attractions set the perfect stage for a couple’s retreat. Vacation homes can be found near places like the Umbrella Cover Museum, a specialty museum with a whimsical collection of umbrella covers, and Commercial Street, a downtown area with unique shops and boutiques. You'll also like the Tate House Museum, a colonial-era home of a British naval officer with period furnishings and tours.

Where to stay around Portland?

Our 2019 property listings offer a large selection of 733 vacation rentals near Portland. From 296 Houses to 110 Cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Portland for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Portland?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Portland:

  • Peaks Island: 77 vacation rentals
  • Downtown Portland: 92 vacation rentals
  • West End: 59 vacation rentals
  • Back Cove: 21 vacation rentals
  • Parkside: 58 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Portland?

HomeAway offers a large selection of vacation rentals near lovely places in Portland. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Eastern Promenade: 1,356 vacation rentals
  • University of Southern Maine: 1,372 vacation rentals
  • Maine Narrow Gauge Railroad Company and Museum: 1,354 vacation rentals
  • Portland Stage: 1,383 vacation rentals
  • Cross Insurance Arena: 1,374 vacation rentals

But there are many other points of interest around Portland listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Portland?

Yes, of course. HomeAway has 296 Houses in Portland. Our other popular types of vacation rentals in Portland include:

  • Cottages: 110 rentals available
  • Cabins: 110 rentals available
  • Condos/Apartments: 294 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Portland?

Yes, you can select your preferred vacation rental with pool among our 106 vacation rentals with pool available in Portland. Please use our search bar to access the selection of vacation rentals available.

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