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Oaktown Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Oaktown holiday 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)
The price is HK$1,121
HK$2,714 total
includes taxes & fees
15 Sept - 16 Sept
Illinois Vacation Rental Home: Pets Welcome
A wooden door with a decorative knocker and a lantern above it.

2. 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 HK$1,020
HK$1,142 total
includes taxes & fees
27 Sept - 28 Sept
Pleasant Grove Farm LLC
A modern kitchen with wooden cabinets, a central island with stools, a built-in stove, and a window providing natural light.

3. Relaxing Small-Town Retreat in Lawrenceville

Relaxing Small-Town Retreat in Lawrenceville
Lawrenceville
10.0 out of 10, Exceptional, (17 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 HK$1,059
HK$1,862 total
includes taxes & fees
20 Sept - 21 Sept
Relaxing Small-Town Retreat in Lawrenceville
A living room with a fireplace, leather sofas, and a clock on the wall.

4. 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.
The price is HK$855
HK$2,784 total
includes taxes & fees
15 Sept - 16 Sept
Illinois Vacation Rental Home: Pets Welcome
A modern living room with a sectional sofa, a flat-screen TV, and a ceiling fan.

5. 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.
The price is HK$925
HK$1,914 total
includes taxes & fees
15 Sept - 16 Sept
Comfortable 2BR on the Square
A kitchen with wooden cabinets, a white refrigerator, and a chalkboard with a motivational quote.

6. 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 HK$2,419
HK$4,326 total
includes taxes & fees
15 Sept - 16 Sept
Peaceful Meadows - Peaceful Meadows
A street view at night with buildings, a car parked on the side, and a tree in the foreground.

7. The Robinson Roost

The Robinson Roost
Robinson
10.0 out of 10, Exceptional, (1 review)
"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 HK$1,062
HK$2,342 total
includes taxes & fees
15 Sept - 16 Sept
The Robinson Roost

8. Modern Tiny Home w/ Hot Tub Retreat

Modern Tiny Home w/ Hot Tub Retreat
Jasonville
9.6 out of 10, Exceptional, (17 reviews)
"Great little cozy place."
United States
DeWayne
The price is HK$1,999
HK$3,153 total
includes taxes & fees
15 Sept - 16 Sept
Modern Tiny Home w/ Hot Tub Retreat
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.

9. 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, (33 reviews)
"Great value"
United States
ERIC
The price is HK$1,129
HK$2,538 total
includes taxes & fees
15 Sept - 16 Sept
Cozy East Side Condo in Washington close to City Park and Hospital
A wooden deck with a view of a lake and grassy fields.

10. 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, (29 reviews)
"Very clean and view was great and a very quiet place to relaxHost was fantastic "
United States
Glen C.
The price is HK$819
HK$1,532 total
includes taxes & fees
22 Sept - 23 Sept
Unique cozy 14x40 Cabin with a nice deck by the water .
A modern kitchen with a microwave, stove, and sink.

11. ACE STAYS: Modern 1 BR apartment in Vincennes

ACE STAYS: Modern 1 BR apartment in Vincennes
Vincennes
The price is HK$635
HK$1,362 total
includes taxes & fees
27 Sept - 28 Sept
ACE STAYS: Modern 1 BR apartment in Vincennes
A bedroom with a bed, dresser, television, and a door.

12. Enjoyable 3-bedroom house in charming Robinson

Enjoyable 3-bedroom house in charming Robinson
Robinson
9.0 out of 10, Wonderful, (2 reviews)
"Will stay there aging. We were in town for a funeral and needed a late check out. The owner worked with us quickly and smoothly to make our stay very comfortable. Thanks!!"
United States
joe s.
The price is HK$823
HK$1,471 total
includes taxes & fees
15 Sept - 16 Sept
Enjoyable 3-bedroom house in charming Robinson
A wooden door with a window, a white shelf with jars and lanterns, and a white wall with a light switch.

13. 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 HK$1,038
HK$1,812 total
includes taxes & fees
23 Sept - 24 Sept
Cozy and relaxing
A living room with a fireplace, a sofa, a coffee table, and decorative wall art.

14. Ace Stays : Vincennes 1BR

Ace Stays : Vincennes 1BR
Vincennes
The price is HK$980
HK$1,723 total
includes taxes & fees
14 Oct - 15 Oct
Ace Stays : Vincennes 1BR
A wooden staircase with white balusters leading to a door labeled "HARRISBURG HOTEL."

15. Quaint 1BR with Kitchenette

Quaint 1BR with Kitchenette
Robinson
10.0 out of 10, Exceptional, (1 review)
The price is HK$659
HK$1,459 total
includes taxes & fees
15 Sept - 16 Sept
Quaint 1BR with Kitchenette
A white door with a decorative glass panel and a small mailbox on the wall.

16. 3 Bed/1 Bath Close to Everything in Robinson

3 Bed/1 Bath Close to Everything in Robinson
Robinson
The price is HK$925
HK$1,797 total
includes taxes & fees
15 Sept - 16 Sept
3 Bed/1 Bath Close to Everything in Robinson
A covered outdoor area with a gravel path leading to a building with stone accents and a wooden pergola.

17. Modern Retreat w/ Private Hot Tub & Bunk Room

Modern Retreat w/ Private Hot Tub & Bunk Room
Jasonville
8.0 out of 10, Very good, (1 review)
"Dishes left in dish washer and hot tub was very dirty because cover was left off."
United States
J C A.
The price is HK$2,906
HK$5,064 total
includes taxes & fees
15 Sept - 16 Sept
Modern Retreat w/ Private Hot Tub & Bunk Room
A bedroom with a wooden headboard, a floral bedspread, a plaid blanket, and a window with curtains.

18. Right off of Main St in Robinson

Right off of Main St in Robinson
Robinson
The price is HK$831
HK$1,722 total
includes taxes & fees
15 Sept - 16 Sept
Right off of Main St in Robinson
A hotel room with a bed, a chair, a window with curtains, and a door.

19. 3 BR House Near Hershey/Marathon

3 BR House Near Hershey/Marathon
Robinson
The price is HK$776
HK$1,659 total
includes taxes & fees
15 Sept - 16 Sept
3 BR House Near Hershey/Marathon
A modern kitchen with a central island, white cabinetry, and a view of the outside through large windows.

20. 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.
The price is HK$871
HK$1,848 total
includes taxes & fees
15 Sept - 16 Sept
2 Bedroom Apartment in the Heart of Robinson
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

Simply Home Inn & Suites

Simply Home Inn & Suites

10/10 Excellent
"Convenient and quiet."
Larry 2-night trip
Posted 6 hours ago
Simply Home Inn & Suites

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:

  • View our selection of featured holiday rentals in Oaktown
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  • Enter your travel dates to view the best deals on holiday rentals in Oaktown while they last

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

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?

The GreyStone House: This holiday home rental outside of Oaktown is located in the city centre, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.