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Oaktown Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Oaktown vacation rentals

A modern kitchen with a microwave, stove, and sink.

1. ACE STAYS: Modern 1 BR apartment in Vincennes

ACE STAYS: Modern 1 BR apartment in Vincennes
Vincennes
$160 nightly
The price is $184
Oct 22 - Oct 23
Total with taxes and fees
ACE STAYS: Modern 1 BR apartment in Vincennes
Interior

2. Studio with Queen Bed

Studio with Queen Bed
Robinson
10.0 out of 10, Exceptional, (1 review)
"Good value. Great location"
United States
Martin
$120 nightly
The price is $121
Oct 11 - Oct 12
Total with taxes and fees
Studio with Queen Bed
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
$140 nightly
The price is $157
Oct 11 - Oct 12
Total with taxes and fees
Pleasant Grove Farm LLC
A black door with a grid pattern, a white door frame, and a small sign above the door reading "103 West Walnut".

4. 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.
$192 nightly
The price is $203
Oct 15 - Oct 16
Total with taxes and fees
Cozy Loft Hideaway in Robinson
A hallway with a white door, a white table with a vase, and a light switch on the wall.

5. Ace Stays : Vincennes 1BR

Ace Stays : Vincennes 1BR
Vincennes
$195 nightly
The price is $224
Nov 6 - Nov 7
Total with taxes and fees
Ace Stays : Vincennes 1BR
A modern kitchen with wooden cabinets, a central island with stools, a built-in stove, and a window providing natural light.

6. 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.
$235 nightly
The price is $249
Oct 12 - Oct 13
Total with taxes and fees
Relaxing Small-Town Retreat in Lawrenceville
A kitchen with wooden cabinets, a central island with two bar stools, a microwave, a refrigerator, and a window with blinds.

7. 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
$210 nightly
The price is $223
Oct 16 - Oct 17
Total with taxes and fees
Enjoyable 3-bedroom house in charming Robinson
A street view at night with buildings, a car parked on the side, and a tree in the foreground.

8. 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.
$297 nightly
The price is $300
Oct 14 - Oct 15
Total with taxes and fees
The Robinson Roost
A bedroom with a bed, a TV, a dresser, and two doors.

9. 3 BR House Near Hershey/Marathon

3 BR House Near Hershey/Marathon
Robinson
$209 nightly
The price is $211
Oct 11 - Oct 12
Total with taxes and fees
3 BR House Near Hershey/Marathon
A wooden staircase with white balusters leading to a door labeled "HARRISBURG HOTEL."

10. Quaint 1BR with Kitchenette

Quaint 1BR with Kitchenette
Robinson
10.0 out of 10, Exceptional, (1 review)
$175 nightly
The price is $185
Oct 11 - Oct 12
Total with taxes and fees
Quaint 1BR with Kitchenette
A wooden deck with a view of a lake and grassy fields.

11. 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, (33 reviews)
"Very clean and view was great and a very quiet place to relaxHost was fantastic "
United States
Glen C.
$174 nightly
The price is $195
Oct 11 - Oct 12
Total with taxes and fees
Unique cozy 14x40 Cabin with a nice deck by the water .
A compact kitchen with a refrigerator, stove, microwave, and dining table with chairs.

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

3 Bed/1 Bath Close to Everything in Robinson
Robinson
$228 nightly
The price is $229
Oct 11 - Oct 12
Total with taxes and fees
3 Bed/1 Bath Close to Everything in 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.
$222 nightly
The price is $249
Oct 25 - Oct 26
Total with taxes and fees
Cozy and relaxing
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!
Robinson
8.8 out of 10, Excellent, (3 reviews)
"Nice place! We watched eclipse on the trip. Had a great time. :DEvolve team answered our questions promptly."
United States
Minfei
$404 nightly
The price is $446
Oct 11 - Oct 12
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, (7 reviews)
"Great place to stay. Host was very welcoming."
United States
Patricia M.
$530 nightly
The price is $562
Oct 12 - Oct 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)
$234 nightly
The price is $247
Oct 13 - Oct 14
Total with taxes and fees
Spacious 3BR on the Square
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.

17. 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
$279 nightly
The price is $324
Oct 12 - Oct 13
Total with taxes and fees
Cozy East Side Condo in Washington close to City Park and Hospital
A spacious kitchen with modern appliances, a dining area with a glass-top table, and a ceiling fan.

18. Updated Robinson Vacation Rental w/ Fireplace!

Updated Robinson Vacation Rental w/ Fireplace!
3.0 star property
Robinson
$394 nightly
The price is $437
Oct 11 - Oct 12
Total with taxes and fees
Updated Robinson Vacation Rental w/ Fireplace!
Private kitchen

19. 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
$363 nightly
The price is $407
Oct 12 - Oct 13
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.

20. 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.
$584 nightly
The price is $654
Oct 12 - Oct 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

Holiday Inn Express Washington by IHG

Holiday Inn Express Washington by IHG

8/10 Good
"The guy at the front desk was perhaps the nicest person I've ever encountered. The hotel was very clean. The third floor (where my room was) hallway seemed a bit "rundown" -- not sure if they were in the middle of some sort of maintenance to it. The room was just fine, and everywhere else was really nice."
Kayloni 1-night trip
Posted 2 days ago
Holiday Inn Express Washington by IHG

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 $157 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.