Oaktown Holiday Rentals

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Holiday Rentals in Oaktown

“Tucked Away” in a quiet and private setting.
10.0 out of 10, Exceptional, (23)
"We enjoyed our stay at this very clean and organized home. The host was great. We would stay again."
The price is NZ$272
per night
19 Jun - 20 Jun
“Tucked Away” in a quiet and private setting.
Eagles Nest Camping Bee Hunter Cabin
9.8 out of 10, Exceptional, (29)
"I enjoyed it so much. The only thing is I swear I saw somewhere that there was a hot tub. Which was 1 main reason we chose there."
Eagles Nest Camping Bee Hunter Cabin
Pleasant Grove Farm LLC
3.0 star property
9.2 out of 10, Wonderful, (94)
"I almost never write reviews for places we stay, but this place is great. Lots of small details. Very comfortable. Definitely the nicest place to stay in the area."
The price is NZ$237
per night
23 Jun - 24 Jun
Pleasant Grove Farm LLC
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Unique cozy 14x40 Cabin with a nice deck by the water .
10.0 out of 10, Exceptional, (6)
"Wonderful weekend, beautiful lake. Loved our stay!"
The price is NZ$343
per night
19 Jun - 20 Jun
Unique cozy 14x40 Cabin with a nice deck by the water .
Eagles Nest Camping Brewer Cabin
10.0 out of 10, Exceptional, (14)
"the cabin was great. very comfortable for our stay. clear very of the eclipse"
Eagles Nest Camping Brewer Cabin
The Chestnut Nest - Robinson
9.8 out of 10, Exceptional, (15)
"Great location. House is roomy with lots of activity areas. Sleeps 8 but hard to feed 8 (only 5 glasses, 7 mugs, fewer forks than spoons and knives). We had room to spread out and really enjoyed the eclipse while we were there."
The Chestnut Nest - Robinson
Cozy East Side Condo in Washington close to City Park and Hospital
10.0 out of 10, Exceptional, (1)
"This was our place to stay on a family trip for the total eclipse in April 2024. Washington, Indiana, was perfect for the eclipse, just about in the center of the strip of totality. This listing seemed perfect for our needs - 3 bedrooms, 2 baths, nicely decorated with WiFi and smart TVs, and a full kitchen. I was so pleased that it was available. This property was better than we expected. Absolutely perfectly set up, with linens and towels and kitchen wares ready for our stay. We were literally...
Cozy East Side Condo in Washington close to City Park and Hospital
Loft Apartment
The price is NZ$189
per night
30 Jun - 1 Jul
Loft Apartment
Lake View Cabin
10.0 out of 10, Exceptional, (55)
"Super caring hosts that even delivered cookies to us multiple times. Very clean and comfortable home. Felt like we were at a private resort. Perfect getaway for enjoying God‘s creation."
Lake View Cabin
The Hide Away
9.4 out of 10, Exceptional, (15)
"Our party of four was in town for the eclipse for a couple of days. The Hide Away was perfect for us. Communication with Tim was great, check-in and check-out were easy. We enjoyed our time in Linton and had a great interaction with everyone we met."
The price is NZ$272
per night
19 Jun - 20 Jun
The Hide Away
Cozy and relaxing
10.0 out of 10, Exceptional, (2)
"It was a wonderful neighborhood that was perfect for our trip. The host was very helpful and inviting."
Cozy and relaxing
Hillenbrand Hideaway- perfectly located!
10.0 out of 10, Exceptional, (6)
"Very clean quiet location"
Hillenbrand Hideaway- perfectly located!
Eagles Nest Camping Black Creek Cabin
10.0 out of 10, Exceptional, (17)
"Fantastic Cabin in quiet rural area. Hostess Deb met us upon our arrival and was very accommodating. Beds were very comfortable. Nice clean cabin. Helped make the eclipse weekend most memorable!"
Eagles Nest Camping Black Creek Cabin
LakeWay II- 4 min from US-41 and Lake Sullivan
10.0 out of 10, Exceptional, (1)
"I was traveling in the area to visit family and needed someplace for two nights. The location was perfect. This property combines an interesting historical past (general store built in 1840) and an efficient, comfortable, well thought out home away from home. I recommend it without hesitation!"
LakeWay II- 4 min from US-41 and Lake Sullivan
Peaceful Cabin By The Lake
9.4 out of 10, Exceptional, (9)
"Perfect location. Close to town but far enough out to enjoy the country side"
Peaceful Cabin By The Lake
Cozy Loft Hideaway in Robinson
10.0 out of 10, Exceptional, (1)
"Cute little place very cozy laundry just across the hall would definitely book again"
Cozy Loft Hideaway in Robinson
Pet-friendly home in Palestine with Fenced Yard! Weekly and monthly discounts!
10.0 out of 10, Exceptional, (2)
"Clean property with great space. Kitchen is very well equipped to cook. Beds are extremely comfortable. Property owner was responsive to requests and provided all the information we needed for a smooth check in. Great stay at a difficult time attending a funeral. We look forward to returning under more joyous circumstances."
Pet-friendly home in Palestine with Fenced Yard! Weekly and monthly discounts!
The GreyStone House
9.8 out of 10, Exceptional, (7)
"We had a large party and needed to divide up between a few homes. This house gave us the luxury of being able to spread out and all have our own space. Central location to everything. Would rent again."
The GreyStone House
Updated Robinson Vacation Rental w/ Fireplace!
10.0 out of 10, Exceptional, (1)
Updated Robinson Vacation Rental w/ Fireplace!
Cozy cottage 4 minutes from Lake Sullivan!
10.0 out of 10, Exceptional, (9)
"We couldn't have asked for a better place to spend the weekend. Very comfortable, beautifully decorated, and great location. All the extra little things, snacks, coffee, toiletries... We really felt like Jaime went above and beyond to make it such a great experience that we can't wait to do it again next year."
Cozy cottage 4 minutes from Lake Sullivan!
Don't see what you're looking for?
See all available properties in Oaktown
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.

Other types of properties in Oaktown you may be interested in

Baymont by Wyndham Washington
2.5 star property
8.0 out of 10, Very good, (539)
"It was very convenient for us and easy to get in and out. I was a bit dismayed at the handicapped shower/bathtub. The handle took both hands at full strength with a washcloth to not hurt your hands. There was also nothing! to hang on to when you tried to step out. That was quite dangerous and needs to be addressed asap. I’m not disabled and it scared me and I worried about my husband who has Parkinson’s. The people were all very nice and helpful all around!"
The price is NZ$183
per night
24 Jun - 25 Jun
Baymont by Wyndham Washington
Comfort Suites
2.5 star property
8.4 out of 10, Very good, (430)
"nice clean and comfortable. would stay again "
The price is NZ$141
per night
1 Jul - 2 Jul
Comfort Suites
Holiday Inn Express Vincennes, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (346)
"The staff was very professional and helpful with local information."
The price is NZ$193
per night
1 Jul - 2 Jul
Holiday Inn Express Vincennes, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oaktown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oaktown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oaktown. Seeing all the best attractions is bound to make you fall in love with Oaktown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oaktown short-term rentals, that won’t be hard to do.

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?

“Tucked Away” in a quiet and private setting.: This holiday home rental outside of Oaktown has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Oaktown?

While you're exploring the area, Rogers Clark National Historical Park and Sullivan County Park are a couple of picturesque spots to get outside and enjoy nature. Vincennes University and Harrison Mansion 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.

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