Oaktown holiday rentals

We found holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Oaktown to find one that's perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a fireplace. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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

Choose a holiday rental for your Oaktown getaway

Learn about the unique charm of Oaktown with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Oaktown

Are you hoping to find things to do while you're in town? Venture out of your holiday home and experience everything that makes Oaktown a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Elks Country Club (16.1 mi / 25.8 km)
  • Deer Run Mary Heath Memorial Golf Course (19 mi / 30.5 km)

Exploring the natural features in Oaktown

Whether you're looking for adventure or just want to spend some time taking in the scenery, Oaktown is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Rogers Clark National Historical Park (14.2 mi / 22.9 km)
  • Sullivan County Park (16.5 mi / 26.5 km)
  • Gregg Park (13.3 mi / 21.3 km)
  • Indiana Territorial Capitol (13.4 mi / 21.6 km)
  • Chippekokee Park (12.7 mi / 20.4 km)
  • Sullivan City Park (15.2 mi / 24.4 km)

Frequently asked questions

How much does it cost to rent a holiday home in Oaktown?
The average price for a holiday home in Oaktown is determined by several factors, like time of year, length of stay and property type. Whether you’re in search of a sprawling villa with space for extended family or an apartment for just you and your sweetheart, just add your dates of travel to discover stays with unbeatable value.
How much does it cost to rent a beach house in Oaktown?
Prices for beach houses in Oaktown differ depending on the type and size of the property and when you plan to travel. Simply enter your dates of travel into Stayz and the number of guests to view available options and prices. From there you can use our filters to refine your search by amenities, ratings, nearby activities and more.
How old do you have to be to rent a holiday home in Oaktown?
The age limit can vary across properties on Stayz, so double-check the rules of the holiday home in Oaktown you want. But normally, it’s 16, 18 or 21.
How long can I rent a holiday home in Oaktown for?
It’s down to the Oaktown property. To look over a list of options offering extended stays, just enter your dates and number of guests into Stayz’s search page. You can look forward to having the property to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and outdoor spaces where the kids can run and play. Keep an eye out for long-term stays that offer weekly or monthly discounts.