Where to stay around Portland?

Our 2019 property listings offer a large selection of 711 vacation rentals near Portland. From 286 Houses to 239 Condos/Apartments, 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: 57 vacation rentals
  • Downtown: 86 vacation rentals
  • East End: 68 vacation rentals
  • West End: 59 vacation rentals
  • Parkside: 55 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: 1,392 vacation rentals
  • Fifth Maine Museum: 1,338 vacation rentals
  • East End Beach: 1,390 vacation rentals
  • Casco Bay Lines Ferry Terminal: 1,393 vacation rentals
  • Victoria Mansion: 1,432 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 286 Houses in Portland. Our other popular types of vacation rentals in Portland include:

  • Condos/Apartments: 239 rentals available
  • Studios: 130 rentals available
  • Cabins: 124 rentals available

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

Can I find a vacation rental with pool in Portland?

Yes, you can select your preferred vacation rental with pool among our 96 vacation rentals with pool available in Portland. Please use our search bar to access the selection of vacation rentals available.

    Portland—a winning combination

    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.

    Portland Old Port’s renaissance

    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.

    Portland’s guiding light

    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.

    How to find the perfect Portland pad

    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.

    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.

    Explore destinations around Portland

    Great Diamond Island
    424 vacation rentals
    Old Orchard Beach
    789 vacation rentals
    1,483 vacation rentals
    379 vacation rentals
    Cape Elizabeth
    1,012 vacation rentals
    854 vacation rentals
    377 vacation rentals
    783 vacation rentals
    387 vacation rentals
    Frye Island
    99 vacation rentals
    652 vacation rentals
    1,174 vacation rentals
    666 vacation rentals
    316 vacation rentals
    773 vacation rentals
    883 vacation rentals
    Long Island
    377 vacation rentals
    212 vacation rentals
    South Portland
    300 vacation rentals
    Chebeague Island
    539 vacation rentals