Vacation rentals in Oaktown

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Top-rated vacation rentals in Oaktown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Loft in Huntingburg

4.92 out of 5 average rating, 119 reviews

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

Mar 12 – 19

G$18,131 GYD per night
Guest favorite

Tiny home in Hymera

4.97 out of 5 average rating, 159 reviews

"Just Enuf" Cabin/Tiny House- NO CLEANING FEE

Brand new cabin/tiny house with a porch swing to relax in at the end of your day. Enjoy your time to simply get away or as a must need sleep over due to travel or work. Dollar General store is just a few blocks away. Located in small rural town near Shakamak State Park and a short drive to Greene-Sullivan State Forest. 35 miles from the Marathon Robinson Refinery. 21 miles from Hoosier Energy Merom Generating Station. 25 miles from Terre Haute. 17 miles from Linton. Quiet neighborhood.

Apr 25 – May 2

G$11,155 GYD per night
Guest favorite

Guesthouse in Hardinsburg

4.95 out of 5 average rating, 171 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Jun 24 – Jul 1

G$24,007 GYD per night

Popular amenities for Oaktown vacation rentals

Other great vacation rentals in Oaktown

Guest favorite

Home in Vincennes

4.96 out of 5 average rating, 26 reviews

Charming 2 Bed, 1 Bath Home Centrally Located

Jun 15 – 22

G$18,055 GYD per night
Superhost

Cabin in Hymera

4.87 out of 5 average rating, 15 reviews

Carousel Cabin

Jan 18 – 25

G$13,982 GYD per night
Guest favorite

Home in Olney

4.96 out of 5 average rating, 25 reviews

Lakeside Lodge with Private Dock and Kids' Kayaks

Aug 13 – 20

G$31,596 GYD per night
Superhost

Loft in Washington

4.86 out of 5 average rating, 72 reviews

Lovely 3 bedroom loft apartment!

Aug 23 – 30

G$28,330 GYD per night
Guest favorite

Home in Bloomfield

5.0 out of 5 average rating, 36 reviews

House in Bloomfield

Sep 1 – 8

G$23,355 GYD per night
Guest favorite

Home in Odon

5.0 out of 5 average rating, 45 reviews

Peaceful Habitation

Jul 19 – 26

G$24,011 GYD per night
Guest favorite

Cottage in Linton

4.94 out of 5 average rating, 62 reviews

Bluegill Cottage

Oct 7 – 14

G$26,503 GYD per night
Superhost

Apartment in Vincennes

4.87 out of 5 average rating, 15 reviews

Unique Historical Apartment

Jul 19 – 26

G$34,581 GYD per night
Guest favorite

Home in Worthington

4.91 out of 5 average rating, 45 reviews

Cozy and quiet with many amenities! Close to Crane

Aug 3 – 10

G$16,494 GYD per night
Guest favorite

Home in Loogootee

4.86 out of 5 average rating, 63 reviews

The Getaway House

May 28 – Jun 4

G$12,543 GYD per night
Guest favorite

Campsite in Jasonville

4.99 out of 5 average rating, 89 reviews

Castaway Lake Side Canvas Cottage Tent

Aug 31 – Sep 7

G$25,731 GYD per night
Guest favorite

Cabin in Bloomfield

4.95 out of 5 average rating, 41 reviews

Peaceful, Secluded Cabin Getaway

Feb 7 – 14

G$23,211 GYD per night

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  5. Oaktown