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Portland holiday lettings

We found 219 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.

Holiday rentals with weekly discounts - Portland

Showing deals for:5 Dec - 12 Dec
  • 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Portland

Find out more about Portland

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)
  • Quincy Cellars (17.4 mi / 27.9 km)
  • Shorewood Country Club (7 mi / 11.2 km)
  • Grape Discovery Center (8.6 mi / 13.8 km)
  • Chautauqua Golf Club (12.1 mi / 19.4 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:

  • Point Gratiot Park (9.1 mi / 14.7 km)
  • Chautauqua Lake (15 mi / 24.1 km)
  • Dewittville Bay (10.3 mi / 16.5 km)
  • Whitney Bay (14 mi / 22.5 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 centre.

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