Ossipee holiday lettings

We found 467 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 8 homes and other holiday rentals in Ossipee that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a pool. You'll be sure to find a property to rent to meet everyone's 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, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Delight in the lakeside landscape of Ossipee

The lake and beaches create a pretty picture of Ossipee. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Ossipee

Are you searching for attractions to visit in the area? Venture out of your cosy holiday rental and experience everything that makes Ossipee a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Brainerd International Raceway (10.7 mi / 17.1 km)
  • Mount Ski Gull (13.1 mi / 21.1 km)
  • Paul Bunyan Land (13.1 mi / 21.1 km)
  • Cragun's Legacy Courses (14.4 mi / 23.1 km)
  • The Classic at Madden's Golf Course (14.8 mi / 23.8 km)
  • Legacy at Cragun's (14.9 mi / 24 km)

Exploring the natural features in Ossipee

Whether you're an adventurous traveller or just want to take in the scenery, Ossipee is a great place to get outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Gull Lake (10.7 mi / 17.3 km)
  • Bay Lake (17.1 mi / 27.6 km)
  • Farm Island Lake (18.7 mi / 30.1 km)
  • Cuyuna Country State Recreation Area (6.8 mi / 10.9 km)
  • Horseshoe Lake (8.1 mi / 13 km)
  • Crosby Memorial Park (9 mi / 14.5 km)

Travelling to and around Ossipee

Fly into Brainerd, MN (BRD-Brainerd Lakes Regional), the closest airport, located 9.6 mi (15.4 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday rental in Ossipee?

A number of things can influence how much you'll pay for a holiday rental in Ossipee, including the season, length of stay and type of property. But, all Vrbo homes have something in common — exceptional value. Just enter your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Ossipee?

The average price for a holiday rental by the beach in Ossipee will depend on when you're going and the size and type of property you want. Find prices quickly and easily on Vrbo by entering your destination and travel dates. Then use the handy filters to pick the number of bedrooms and amenities that you require, like WiFi, a pool and air conditioning.

How old do you have to be to rent a holiday rental in Ossipee?

The minimum required age is typically 16, 18 or 21. It can change between properties on Vrbo, so check the rules of your chosen Ossipee holiday home before booking your trip.

How long can I rent a holiday rental in Ossipee for?

The amount of time you can book an Ossipee holiday rental for differs depending on the property. Just enter your travel dates to find options offering longer term stays. They include the things you need to make your extended holiday more enjoyable and comfortable, such as air conditioning and laundries. Some properties may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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