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Oaktown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Oaktown vacation rentals

A living room with a fireplace, leather sofas, and a clock on the wall.

1. Illinois Vacation Rental Home: Pets Welcome

Illinois Vacation Rental Home: Pets Welcome
3.0 star property
Palestine
10.0 out of 10, Exceptional, (1 review)
Illinois Vacation Rental Home: Pets Welcome
A living room with a fireplace, leather sofas, and a clock on the wall.

2. Illinois Vacation Rental Home: Pets Welcome

Illinois Vacation Rental Home: Pets Welcome
Palestine
7.0 out of 10, Good, (2 reviews)
"Clean and comfortable. "
United States
Dori N.
Illinois Vacation Rental Home: Pets Welcome
A wooden door with a decorative knocker and a lantern above it.

3. Pleasant Grove Farm LLC

Pleasant Grove Farm LLC
3.0 star property
Lyons
9.4 out of 10, Exceptional, (105 reviews)
"This is our favorite place to stay every Labor Day weekend. It’s home away from home!"
United States
Craig
The price is ￥22,099
￥24,750 total
includes taxes & fees
Oct 5 - Oct 6
Pleasant Grove Farm LLC
A modern kitchen with a microwave, stove, and sink.

4. ACE STAYS: Modern 1 BR apartment in Vincennes

ACE STAYS: Modern 1 BR apartment in Vincennes
Vincennes
The price is ￥14,207
￥29,045 total
includes taxes & fees
Oct 22 - Oct 23
ACE STAYS: Modern 1 BR apartment in Vincennes
Interior

5. Studio with Queen Bed

Studio with Queen Bed
Robinson
10.0 out of 10, Exceptional, (1 review)
"Good value. Great location"
United States
Martin
The price is ￥7,893
￥19,132 total
includes taxes & fees
Oct 10 - Oct 11
Studio with Queen Bed
A black door with a grid pattern, a white door frame, and a small sign above the door reading "103 West Walnut".

6. Cozy Loft Hideaway in Robinson

Cozy Loft Hideaway in Robinson
Robinson
10.0 out of 10, Exceptional, (3 reviews)
"Very pleasant stay. The loft was very clean and cozy as advertised."
United States
Mitchell M.
The price is ￥15,627
￥32,197 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Loft Hideaway in Robinson
A modern kitchen with wooden cabinets, a central island with stools, a built-in stove, and a window providing natural light.

7. Relaxing Small-Town Retreat in Lawrenceville

Relaxing Small-Town Retreat in Lawrenceville
Lawrenceville
10.0 out of 10, Exceptional, (18 reviews)
"We come to Lawranceville Illinois several times a year from Georgia and we always stay there!! We love it! Very comfortable and cozy!!!"
United States
Lori L.
The price is ￥21,310
￥39,313 total
includes taxes & fees
Oct 7 - Oct 8
Relaxing Small-Town Retreat in Lawrenceville
A hallway with a white door, a white table with a vase, and a light switch on the wall.

8. Ace Stays : Vincennes 1BR

Ace Stays : Vincennes 1BR
Vincennes
The price is ￥19,731
￥35,398 total
includes taxes & fees
Oct 16 - Oct 17
Ace Stays : Vincennes 1BR
A street view at night with buildings, a car parked on the side, and a tree in the foreground.

9. The Robinson Roost

The Robinson Roost
Robinson
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful property and great host. Great communication, clean, organized, and all necessary amenities. We will definitely be back!"
United States
Cara T.
The price is ￥21,381
￥47,302 total
includes taxes & fees
Oct 8 - Oct 9
The Robinson Roost
A kitchen with wooden cabinets, a central island with two bar stools, a microwave, a refrigerator, and a window with blinds.

10. Enjoyable 3-bedroom house in charming Robinson

Enjoyable 3-bedroom house in charming Robinson
Robinson
9.4 out of 10, Exceptional, (3 reviews)
"Convenient, had a nice stay"
United States
Karen
The price is ￥16,574
￥29,444 total
includes taxes & fees
Oct 12 - Oct 13
Enjoyable 3-bedroom house in charming Robinson
A bedroom with a bed, a TV, a dresser, and two doors.

11. 3 BR House Near Hershey/Marathon

3 BR House Near Hershey/Marathon
Robinson
The price is ￥15,627
￥33,393 total
includes taxes & fees
Oct 5 - Oct 6
3 BR House Near Hershey/Marathon
A wooden staircase with white balusters leading to a door labeled "HARRISBURG HOTEL."

12. Quaint 1BR with Kitchenette

Quaint 1BR with Kitchenette
Robinson
10.0 out of 10, Exceptional, (1 review)
The price is ￥13,259
￥29,361 total
includes taxes & fees
Oct 5 - Oct 6
Quaint 1BR with Kitchenette
A wooden deck with a view of a lake and grassy fields.

13. Unique cozy 14x40 Cabin with a nice deck by the water .

Unique cozy 14x40 Cabin with a nice deck by the water .
Jasonville
9.8 out of 10, Exceptional, (32 reviews)
"Very clean and view was great and a very quiet place to relaxHost was fantastic "
United States
Glen C.
The price is ￥16,480
￥31,187 total
includes taxes & fees
Oct 12 - Oct 13
Unique cozy 14x40 Cabin with a nice deck by the water .
A compact kitchen with a refrigerator, stove, microwave, and dining table with chairs.

14. 3 Bed/1 Bath Close to Everything in Robinson

3 Bed/1 Bath Close to Everything in Robinson
Robinson
The price is ￥18,626
￥36,179 total
includes taxes & fees
Oct 11 - Oct 12
3 Bed/1 Bath Close to Everything in Robinson
A modern kitchen with a central island, white cabinetry, and a view of the outside through large windows.

15. 2 Bedroom Apartment in the Heart of Robinson

2 Bedroom Apartment in the Heart of Robinson
Robinson
10.0 out of 10, Exceptional, (3 reviews)
"It was a perfect location, we got up and went to all the shops in the square, we will definitely be back "
United States
Betty D.
2 Bedroom Apartment in the Heart of Robinson
A modern living room with a sectional sofa, a flat-screen TV, and a ceiling fan.

16. Comfortable 2BR on the Square

Comfortable 2BR on the Square
Robinson
10.0 out of 10, Exceptional, (4 reviews)
"Host communication was very good, apartment was as described. Stayed here for junior golf tournament."
United States
Brian D.
Comfortable 2BR on the Square
A wooden door with a window, a white shelf with jars and lanterns, and a white wall with a light switch.

17. Cozy and relaxing

Cozy and relaxing
Linton
9.6 out of 10, Exceptional, (13 reviews)
"The property was very clean and as advertised. We had a wonderful stay!"
United States
Jason L.
The price is ￥23,204
￥39,601 total
includes taxes & fees
Oct 25 - Oct 26
Cozy and relaxing
A kitchen with wooden cabinets, a white refrigerator, and a chalkboard with a motivational quote.

18. Peaceful Meadows - Peaceful Meadows

Peaceful Meadows - Peaceful Meadows
Flat Rock
9.8 out of 10, Exceptional, (6 reviews)
"Great place to stay. Host was very welcoming."
United States
Patricia M.
The price is ￥48,686
￥87,746 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful Meadows - Peaceful Meadows
A living room with a sofa, coffee table, and TV. There is a kitchen area with cabinets and a refrigerator. A ceiling fan is visible, and a welcome sign is on the wall.

19. Cozy East Side Condo in Washington close to City Park and Hospital

Cozy East Side Condo in Washington close to City Park and Hospital
Washington
10.0 out of 10, Exceptional, (36 reviews)
"Great value"
United States
ERIC
The price is ￥22,730
￥51,086 total
includes taxes & fees
Oct 8 - Oct 9
Cozy East Side Condo in Washington close to City Park and Hospital
A living room with a grey sofa, a black coffee table, a TV stand, and a patterned rug. There are two stools and a kitchen area visible in the background.

20. Spacious 3BR on the Square

Spacious 3BR on the Square
Robinson
2.0 out of 10, (1 review)
The price is ￥17,521
￥39,034 total
includes taxes & fees
Oct 13 - Oct 14
Spacious 3BR on the Square
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.
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Top Oaktown Hotel Reviews

Unique cozy 14x40 Cabin with a nice deck by the water .

Unique cozy 14x40 Cabin with a nice deck by the water .

10/10 Excellent
"Very nice place. More pictures might help. It is nicer than advertised!"
Mel Z. 5-night trip
Posted 10 hours ago
Unique cozy 14x40 Cabin with a nice deck by the water .

Find out more about Oaktown

Search for holiday rentals in Oaktown on Expedia! You can easily find your home rentals, villas, holiday apartments in Oaktown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Oaktown!

Frequently asked questions

Can I find vacation rentals in Oaktown?

Yes, we give you a choice of vacation rentals near top points of interest in Oaktown, or you can choose a secluded option if you're looking for relaxation.

What's the top vacation rental in Oaktown?

The GreyStone House: This vacation home rental outside of Oaktown is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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. Fife Opera House and Vincennes University are a couple of places you'll find in the larger area.

What’s a vacation rental in Oaktown like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Oaktown. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips.