Oaktown Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oaktown holiday rentals

Cottage in Linton

Pleasant Grove Farm LLC
3.0 star property
9.4 out of 10, Exceptional, (101)
"This is our favorite place to stay every Labor Day weekend. It’s home away from home!"
United States
Craig
The price is AU$218
includes taxes & fees
11 Jan - 12 Jan 2026
Pleasant Grove Farm LLC
10.0 out of 10, Exceptional, (2)
"Host was very accommodating. Would definitely book again. "
United States
Beth V.
The price is AU$281
includes taxes & fees
12 Dec - 13 Dec
Pine Oaks Cabin includes Guest Pole Barn. Modern comfort meets county living.
9.8 out of 10, Exceptional, (9)
"Great stay."
United States
Gerald B.
The price is AU$378
includes taxes & fees
12 Dec - 13 Dec
Charming 2-bedroom apartment with WiFi, AC in Pleasant Lawrenceville
9.8 out of 10, Exceptional, (20)
"The property was spacious, very clean, updated and in a great location. "
United States
Richard E.
The price is AU$490
includes taxes & fees
12 Dec - 13 Dec
Cozy East Side Condo in Washington close to City Park and Hospital
10.0 out of 10, Exceptional, (16)
"Great place to stay, clean and comfortable "
United States
Ann G.
The price is AU$313
includes taxes & fees
15 Dec - 16 Dec
Cozy cottage 4 minutes from Lake Sullivan!

Apartment in Robinson

Cozy Loft Hideaway in Robinson
10.0 out of 10, Exceptional, (3)
"Very pleasant stay. The loft was very clean and cozy as advertised."
United States
Mitchell M.
The price is AU$277
includes taxes & fees
12 Dec - 13 Dec
Cozy Loft Hideaway in Robinson

Holiday Home in Linton

Cozy and relaxing
9.4 out of 10, Exceptional, (9)
"The property was very clean and as advertised. We had a wonderful stay!"
United States
Jason L.
The price is AU$352
includes taxes & fees
18 Dec - 19 Dec
Cozy and relaxing
10.0 out of 10, Exceptional, (6)
"Super cute, great location, would definitely stay here again "
United States
Melinda S.
The price is AU$347
includes taxes & fees
15 Dec - 16 Dec
LakeWay II- 4 min from US-41 and Lake Sullivan
The price is AU$181
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 1-bedroom apartment in historic Palestine in peaceful neighborhood

Apartment in Robinson

Studio with Queen Bed
The price is AU$212
includes taxes & fees
29 Dec - 30 Dec
Studio with Queen Bed
2.0 star property
5.0 out of 10, (2)
"For the price paid, it was well worth it and comfortable. Door lock was a bit sticky, but the owner mentioned was going to replace it after my stay. Definitely would stay here again should my work schedule me odd hours. "
United States
Robert
The price is AU$335
includes taxes & fees
23 Dec - 24 Dec
1 Bedroom Apartment Near Marathon and Hershey

Apartment in Robinson

Quaint 1BR with Kitchenette
The price is AU$282
includes taxes & fees
31 Dec - 1 Jan 2026
Quaint 1BR with Kitchenette
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Oaktown Hotel Reviews

Find out more about Oaktown

Everything you need to know about Oaktown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oaktown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oaktown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oaktown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oaktown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oaktown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oaktown holiday rentals we have selected for you start as low as AU$218 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oaktown rentals

At Expedia, we put the best Oaktown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oaktown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oaktown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oaktown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oaktown?

Yes, there are holiday rentals close to the most popular sights in Oaktown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oaktown has to offer?

Cozy and relaxing: This holiday home rental outside of Oaktown offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

What’s there to see and do in Oaktown?

While you're exploring the area, Indiana Territorial Capitol and Sullivan City Park are a couple of picturesque spots to get outside and enjoy nature. Fife Opera House and Vincennes University are a couple of places you'll find in the wider area.

What’s a holiday rental in Oaktown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oaktown. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.