Photo by Matthew Jay

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.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

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?
The most in-demand types of vacation rentals in Portland are houses. Ready for more choices? Vrbo has plenty of options to match the unique needs of our guests, so you’ll see vacation homes in loads of sizes and shapes. The perfect fit is waiting for you — get hold of yours today.
How much does it cost to rent a vacation rental in Portland?
Length of stay, property type and time of year are some of the things that can influence the price of a vacation home. Simply click on your travel dates to find your ideal escape. From comfy cabins to sprawling luxury villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Portland?
The average price for a vacation home by the beach in Portland depends on when you’re going and the type and size of property you want. You can easily find prices on Vrbo by entering the dates you’ll be traveling. Then use our filter tool to pick the number of bedrooms and amenities that you require, like a pool, WiFi and air conditioning.
Are there pet-friendly vacation rentals in Portland?
With eight vacation rentals that welcome four-legged guests, your furry buddy can join in the fun on your Portland getaway. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
What are popular rental amenities in Portland?
When it comes to rental amenities that people are on the lookout for in Portland, tennis, a barbecue grill and a water view are the most popular. With Vrbo vacation rentals, there are choices to fit your taste and style, whether you’re planning to get away with relatives, friends or even pets.
Are there large group vacation rentals in Portland?
Take your pick of six vacation rentals in Portland that can host 10 or more guests. Whether you’re planning a trip with the family or some kind of special event, there’s plenty of space to get your loved ones together under the same roof.
Are there vacation rentals in Portland that welcome kids?
With eight family-friendly vacation properties to pick from in Portland, now is an awesome time to introduce your children to the excitement of travel. Click on our “Properties good for families” filter to discover stays packed with conveniences ideal for traveling families, such as kitchens, backyards, bunk beds and entertainment areas.
What are the top attractions for families in Portland?
You’ll find lots of wonderful things to see and do with the family in Portland, including:

  • McClurg Museum
  • Darwin R. Barker Historical Museum
  • Lake Erie State Park

Are there vacation rentals with WiFi in Portland?
Portland has seven vacation rentals with WiFi, so you’ll be able to stay connected while you’re traveling. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with the family to updating your social media, these Vrbo homes make it a breeze to get online.
How can I find vacation rentals with air conditioning in Portland?
Portland has six vacation rentals where you can wind down in air-conditioned comfort. To locate a stay on Vrbo with this amenity, enter your desired 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 is generally 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your preferred Portland vacation rental before booking your stay.
How long can I rent a vacation rental in Portland for?
It’s really down to the Portland property. To see all available options offering extended stays, simply enter your travel dates and guest number into Vrbo’s search page. Look forward to having the entire property to yourself, as well as amenities such as air conditioning, a kitchen and an outdoor space to run around in. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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