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Oaktown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Oaktown vacation rentals

A corner building with a bay window and a brick facade.

1. Studio with Queen Bed

Studio with Queen Bed
Robinson
9.0 out of 10, Wonderful, (2 reviews)
"Good value. Great location"
United States
Martin
$120 nightly
The price is $121
Nov 11 - Nov 12
Total with taxes and fees
Studio with Queen Bed
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
9.6 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
$140 nightly
The price is $157
Nov 11 - Nov 12
Total with taxes and fees
Pleasant Grove Farm LLC
A living room with a fireplace, leather sofas, and a clock on the wall.

3. 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)
$327 nightly
The price is $346
Nov 23 - Nov 24
Total with taxes and fees
Illinois Vacation Rental Home: Pets Welcome
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
10.0 out of 10, Exceptional, (1 review)
"Everything was great ! Would recommend maybe some lights to illuminate some rooms when lights are off ? We had to have a nightstand light on to see anything because the whole place is pitch black when everything is off . But everything was accommodating :)"
United States
adam
$148 nightly
The price is $170
Nov 25 - Nov 26
Total with taxes and fees
ACE STAYS: Modern 1 BR apartment in Vincennes
A living room with a fireplace, leather sofas, and a clock on the wall.

5. 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.
$311 nightly
The price is $330
Nov 23 - Nov 24
Total with taxes and fees
Illinois Vacation Rental Home: Pets Welcome
A living room with a fireplace, a sofa, a coffee table, and decorative wall art.

6. Ace Stays : Vincennes 1BR

Ace Stays : Vincennes 1BR
Vincennes
$185 nightly
The price is $213
Nov 11 - Nov 12
Total with taxes and fees
Ace Stays : Vincennes 1BR
A laundry room with two washing machines, a bed in the background, and a ceiling fan.

7. Centrally Located 2-bedroom house in Robinson

Centrally Located 2-bedroom house in Robinson
Robinson
$218 nightly
The price is $218
Nov 20 - Nov 21
Total with taxes and fees
Centrally Located 2-bedroom house in Robinson
A modern kitchen with wooden cabinets, a central island with stools, a built-in stove, and a window providing natural light.

8. Relaxing Small-Town Retreat in Lawrenceville

Relaxing Small-Town Retreat in Lawrenceville
Lawrenceville
10.0 out of 10, Exceptional, (19 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.
$223 nightly
The price is $236
Nov 12 - Nov 13
Total with taxes and fees
Relaxing Small-Town Retreat in Lawrenceville
A compact living space with a kitchenette, a dining area with two chairs, a small table, a sofa, and a staircase with decorative railings.

9. 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.
$194 nightly
The price is $205
Nov 12 - Nov 13
Total with taxes and fees
Cozy Loft Hideaway in Robinson
A hotel room with two beds, a ceiling fan, a night view through the window, and a painting on the wall.

10. 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.
$283 nightly
The price is $285
Nov 24 - Nov 25
Total with taxes and fees
The Robinson Roost
A compact kitchen with white cabinets, a black stove, and a refrigerator.

11. 3 BR House Near Hershey/Marathon

3 BR House Near Hershey/Marathon
Robinson
$201 nightly
The price is $202
Nov 17 - Nov 18
Total with taxes and fees
3 BR House Near Hershey/Marathon
A compact kitchen with a gas stove, a dining table with chairs, a sink, and a window providing a view of the outdoors.

12. 3 Bed/1 Bath Close to Everything in Robinson

3 Bed/1 Bath Close to Everything in Robinson
Robinson
$240 nightly
The price is $241
Nov 12 - Nov 13
Total with taxes and fees
3 Bed/1 Bath Close to Everything in Robinson
A spacious kitchen with modern appliances, a dining area with a glass-top table, and a ceiling fan.

13. Updated Robinson Vacation Rental w/ Fireplace!

Updated Robinson Vacation Rental w/ Fireplace!
Robinson
8.6 out of 10, Excellent, (4 reviews)
"Nice place! We watched eclipse on the trip. Had a great time. :DEvolve team answered our questions promptly."
United States
Minfei
$372 nightly
The price is $412
Nov 13 - Nov 14
Total with taxes and fees
Updated Robinson Vacation Rental w/ Fireplace!
A spacious kitchen with modern appliances, a dining area with a glass-top table, and a ceiling fan.

14. Updated Robinson Vacation Rental w/ Fireplace!

Updated Robinson Vacation Rental w/ Fireplace!
3.0 star property
Robinson
$394 nightly
The price is $437
Nov 13 - Nov 14
Total with taxes and fees
Updated Robinson Vacation Rental w/ Fireplace!
A kitchen with wooden cabinets, a white refrigerator, and a chalkboard with a motivational quote.

15. Peaceful Meadows - Peaceful Meadows

Peaceful Meadows - Peaceful Meadows
Flat Rock
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. Host was very welcoming."
United States
Patricia M.
$504 nightly
The price is $534
Nov 12 - Nov 13
Total with taxes and fees
Peaceful Meadows - Peaceful Meadows
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.

16. Spacious 3BR on the Square

Spacious 3BR on the Square
Robinson
2.0 out of 10, (1 review)
$231 nightly
The price is $244
Nov 12 - Nov 13
Total with taxes and fees
Spacious 3BR on the Square
Private kitchen

17. Modern Tiny Home w/ Hot Tub Retreat

Modern Tiny Home w/ Hot Tub Retreat
Jasonville
9.6 out of 10, Exceptional, (20 reviews)
"Had a relaxing time here and the place was very clean, the snacks and goodies left were appreciated and the hot tub was the best part, very clean and very relaxing!"
United States
Michelle E.
$345 nightly
The price is $387
Nov 11 - Nov 12
Total with taxes and fees
Modern Tiny Home w/ Hot Tub Retreat
A covered outdoor area with a gravel path leading to a building with stone accents and a wooden pergola.

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

Modern Retreat w/ Private Hot Tub & Bunk Room
Jasonville
9.0 out of 10, Wonderful, (2 reviews)
"One of the best rentals we’ve been to! Highly recommend! Thanks so much for the cake, what a pleasant surprise!"
United States
Lisa P.
$540 nightly
The price is $605
Nov 12 - Nov 13
Total with taxes and fees
Modern Retreat w/ Private Hot Tub & Bunk Room
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

Hampton Inn Vincennes

Hampton Inn Vincennes

10/10 Excellent
"Very nice place, clean, spacious room, close to several shopping and restaurants, nice pool and breakfast. Would definitely stay here again."
P 1-night trip
Posted 2 days ago
Hampton Inn Vincennes

Find out more about Oaktown

Everything you need to know about Oaktown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oaktown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oaktown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oaktown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oaktown rentals

At Expedia, we put the best Oaktown vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.