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Portland holiday rentals

We found holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Portland that are perfect for your trip. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a pool and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • 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, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Portland getaway

Learn about the unique charm of Portland with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 hoping to discover top things to see and do during your stay? Venture out of your cosy holiday rental and experience everything that Portland has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for fun outdoor activities or just want to appreciate the scenery, Portland is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Chautauqua Lake (15 mi / 24.1 km)
  • Point Gratiot Park (9.1 mi / 14.7 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 centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Portland?
The most in-demand types of holiday homes in Portland are houses. Ready for more choices? Stayz has plenty of options to match the unique needs of our guests, so you’ll see holiday 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 holiday home in Portland?
Length of stay, property type and time of year are some of the things that can influence the price of a holiday home. Simply click on your travel dates to find your ideal escape. From comfy cabins to sprawling luxury villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Portland?
The average price for a holiday 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 Stayz by entering the dates you’ll be travelling. 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 holiday homes in Portland?
With eight holiday homes 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 holiday homes and find your pawfect pad on Stayz.
What are popular home amenities in Portland?
When it comes to home amenities that people are on the lookout for in Portland, tennis, a barbecue grill and a water view are the most popular. With Stayz holiday homes, 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 holiday homes in Portland?
Take your pick of six holiday homes 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 holiday homes in Portland that welcome kids?
With eight family-friendly holiday 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 travelling 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 holiday homes with WiFi in Portland?
Portland has seven holiday homes with WiFi, so you’ll be able to stay connected while you’re travelling. 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 Stayz homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Portland?
Portland has six holiday homes where you can wind down in air-conditioned comfort. To locate a stay on Stayz 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 holiday home in Portland?
The minimum age is generally 16, 18 or 21. It can differ across properties on Stayz, so look at the rules of your preferred Portland holiday home before booking your stay.
How long can I rent a holiday home 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 Stayz’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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