Portland vacation rentals

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Best Portland vacation rentals

Most recommended vacation rentals in Portland

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East End Annex
8.4 Very good
C$ 260+
C$ 260+
Free Wi-Fi

Good to know

Low season

May

High season

November

Average price (weeknight)

C$ 409

Average price (weekend night)

C$ 285
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 67% rise in price.
Average Sun. - Thu. price over the last 2 weeks.
Average Fri. & Sat. price over the last 2 weeks.

When to book a vacation rental in Portland

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Portland vacation rental deals

  • If you want to enjoy some local history on your trip, you should look for Portland holiday rentals that are in the centre of the city, where many of the main attractions are. For example, West End Retreat @ The Arts District is located a short walk from Victoria Mansion, which is a popular historical landmark.
  • For those that want to enjoy some of the best food that the city has to offer, you should look for Portland holiday rentals that are near East Bayside. For instance, Panoramic Water, Island & City Views W/Private Roof Deck is located only a short distance from popular eateries like Chong Tu Bot and Terlingua.
  • If want to enjoy a holiday by the coast, you should look for Portland house rentals that are close to the beach. For example, Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants is only about a 10min walk to East End Beach, which is a calm beach that offers a range of activities.
  • To make the most of the hiking trails that are in the city, you should look for Portland holiday rentals in the East End. For example, if you stayed at Enjoy Portland With Family or Friends, you would be close to popular walks like the Eastern Promenade Trail.
  • If you are looking to hire a car during your visit to Portland, you should look for properties that provide you with parking areas. For instance, Adorable Portland Getaway on the Eastern Promenade typically provides parking spaces to its guests.
  • Vacation rentals in Portland are around 56% more expensive than hotels on average. Search here to compare prices for all accommodation types in Portland.
  • The best vacation rental properties in Portland are Brand New 1 Bedroom Apartment in Portland (10.0, 22 reviews), The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries (10.0, 29), and Completely remodeled 2 bedroom apartment in Portland's West End (10.0, 20), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Portland, you should consider visiting during the low season. The cheapest vacation homes in Portland can be found in June and July.
  • The cheapest night for renting a vacation home in Portland is Tuesday. In contrast, the most expensive is Monday.
  • Book your Portland vacation rental at least 69 days before your stay begins to get the best price.
  • The cheapest Portland vacation rental found on KAYAK in the last 2 weeks was C$ 114, while the most expensive was C$ 289.

FAQs when booking a vacation home in Portland

  • How much is a vacation rental for a week in Portland?

    The average price for a weekly Portland vacation rental found by KAYAK users in the last 2 weeks is C$ 4,244.

  • How much is a vacation rental for a month in Portland?

    The average price for a monthly Portland vacation rental found by KAYAK users in the last 2 weeks is C$ 18,188.

  • What types of vacation rentals are available in Portland?

    There are loads of different property types that you can make your vacation home in Portland. You’ll find houses, apartments, condos, cottages and luxury tents.

  • What are some of the most-loved vacation rentals available in Portland?

    There are many types of properties available for Portland vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Victorian by the Sea and Kineo View Lodge.

  • Are there any pet-friendly vacation rentals in Portland?

    There are a number of dog and pet-friendly Portland vacation rentals, with around 17% allowing you to bring your pet along with you.

  • How much is a vacation rental in Portland?

    KAYAK users have found vacation rentals in Portland for as cheap as C$ 275 in the last 3 days. The average price is C$ 606.

  • How much is a vacation rental in Portland for tonight?

    In the last 72 hours, users have found Portland vacation rentals for tonight for as low as C$ 213. Search here for similar prices

  • How can I find vacation rentals near me in Portland?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • What are the benefits of a self-catered property?

    When you’re in the U.S. you will find that there are many great places to eat, but it can be expensive to eat out every day. If you get a self-catered property, you’ll have the option to dine in whenever you fancy. For example, Glorious Getaway On Portland's Eastern Promenade provides facilities like an oven and cooktop, so you can cook as much as you like. There is also a range of shops nearby, where you can pick up fresh ingredients for your stay.

  • Where is best to stay in Portland for nightlife?

    If you want to go to the best bars and pubs, you should look for accommodation that’s in the centre of the city. For example, Bright & Spacious Apartment with Amazing Shower is only a short distance from popular establishments like Blackstones and The Jewel Box.

  • What options are there for Portland properties that have swimming pools?

    If you want to swim but prefer to avoid the sea, you will be pleased to know that there are properties that have pools. For example, Close To Downtown With Hot Tub! has an outdoor pool for its guests as well as a spa for you to use.

  • Where is best to stay to be close to the airport?

    If you want to be close to Portland International Jetport (PWM), then you should stay close to Highway 95, so you’ll be close to the terminal. For example, Beautifully Spacious with Charm is about a 12min drive from the airport.

Where to stay in Portland?

Our map will help you find the perfect place to stay in Portland by showing you the exact location of each vacation rental.