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Portland vacation rentals

We found 214 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Portland that are perfect for your trip. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, like cable TV and a washer and dryer. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.
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Find the perfect vacation rental for your Portland getaway

Experience the unique character of Portland with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Portland

Are you looking for attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Portland a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Chautauqua Belle Steamboat (9.8 mi / 15.7 km)
  • Midway State Park (12.7 mi / 20.4 km)
  • Willow Creek Winery (14.7 mi / 23.7 km)
  • Quincy Cellars (17.4 mi / 27.9 km)
  • Grape Discovery Center (8.6 mi / 13.8 km)
  • Chautauqua Bookstore (9 mi / 14.6 km)

Exploring the natural landscape of Portland

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Portland. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Chautauqua Lake (15 mi / 24.1 km)
  • Point Gratiot Park (9.1 mi / 14.7 km)
  • Dewittville Bay (10.3 mi / 16.5 km)
  • Ripley Community Park (14.9 mi / 23.9 km)
  • Fishermans Beach (18.5 mi / 29.8 km)

How to get to and around Portland

Fly into Jamestown, NY (JHW-Chautauqua County), the closest airport, located 18.7 mi (30.1 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Portland?
Cottages are the most popular type of vacation rental in Portland, according to our data. Even if you have a different idea about what you’d like, Vrbo has vacation homes in all shapes and sizes. Look through our options to find your perfect pad.
How much does it cost to rent a vacation rental in Portland?
The average price for a vacation rental in Portland depends on several factors, such as season, property type and length of stay. Whether you’re dreaming about a sprawling villa with a pool or a comfy cabin just enough for two, just enter your travel dates to view stays with great value.
How much does it cost to rent a beach house in Portland?
Prices for beach houses in Portland differ depending on the type and size of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use our filters to narrow your search by ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Portland?
With nine properties that allow pets, your furry companion can also come along on your Portland vacation. Use our filter tool to browse our pet-friendly vacation rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Portland?
Tick the “pool” box in our handy filter tool and you can choose from two houses with private pools in Portland on Vrbo. Morning swim, sunset soak or midnight dip? Leisure time is up to you when your Vrbo vacation home comes with a swimming pool.
What are popular rental amenities in Portland?
Tennis, a water view and a fireplace are the most popular rental amenities in Portland. Whether you’re heading away as a party of one, with your significant other or a group of best friends, Vrbo can help you find a vacation rental that suits your style with all the extras you’re looking for.
Are there large group vacation rentals in Portland?
With five properties that can sleep 10 or more guests in Portland, there’s no need to keep your invite list short. From family get-togethers to special events like birthday and Christmas parties, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Portland that welcome kids?
Portland has nine family-friendly vacation rentals. And finding a stay that welcomes kids is simple with Vrbo’s “Properties good for families” filter. On top of having the whole place to yourselves, you’ll get access to conveniences and perks such as bunk beds, pools and kitchens.
Are there vacation rentals with WiFi in Portland?
Take your pick of eight vacation rentals with WiFi in Portland. If you want to disconnect from the world on your trip, but still want to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Portland?
Portland has seven vacation rentals where you’ll be able to unwind in air-conditioned comfort. To book a stay on Vrbo that has this amenity, choose your travel dates and use the convenient filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Portland?
The minimum age permitted can differ between properties on Vrbo, so be sure to check the rules of the vacation home in Portland you’re considering. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Portland for?
It’s really down to the Portland property. To look at a list of options offering extended stays, simply enter your dates and guest number into Vrbo’s search page. Enjoy having the entire place to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and an outdoor space where the kids can run and play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Portland?
In Portland, you’ll find some incredible deals and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re planning a mini escape or a few weeks away, we offer a host of options to suit your needs and budget.

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