Vacation rentals in Underwood

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Top-rated vacation rentals in Underwood

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

Guest favorite

Train in Lawrenceburg

4.98 out of 5 average rating, 250 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Aug 30 – Sep 6

$133 per night
Guest favorite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 149 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Dec 7 – 14

$127 per night
Guest favorite

Farm stay in Williamstown

4.99 out of 5 average rating, 372 reviews

Mabel’s Cabin

Rural Retreat Welcome to Simpson Ridge Farm Come stay at our Amish-built cabin, nestled on a 3rd generation family-owned farm, in the heart of the pastoral Kentucky bluegrass. Take in the tranquil views on the front porch or back deck, as your surrounded by God's creations. This 420 sq. ft cozy retreat offers a comfortable queen size bed, full bath with walk-in shower, WiFi, and an equipped kitchen. Convenient location minutes from The Ark Encounter, Exit 154 on I-75 in Williamstown, Ky.

Sep 1 – 8

$111 per night

Popular amenities for Underwood vacation rentals

Other great vacation rentals in Underwood

Guest favorite

Farm stay in Paoli

4.97 out of 5 average rating, 150 reviews

Brambleberry Farm Off-Grid Cabin

Jul 3 – 10

$86 per night
Guest favorite

Guesthouse in Georgetown

4.92 out of 5 average rating, 185 reviews

Indian Creek Barn Cottage w/ EV & RV Charger

Jul 25 – Aug 1

$80 per night
Guest favorite

Guesthouse in Louisville

4.93 out of 5 average rating, 774 reviews

HIghlands Modern Get Away

Jun 4 – 11

$79 per night
Guest favorite

Home in Stamping Ground

4.97 out of 5 average rating, 596 reviews

Buffalo Springs Distilling Company

Dec 1 – 8

$138 per night
Guest favorite

Cabin in Bedford

4.97 out of 5 average rating, 218 reviews

River Rock Cabin

Jul 31 – Aug 7

$114 per night
Guest favorite

Treehouse in Georgetown

4.94 out of 5 average rating, 166 reviews

★Escape & Relax ~ Breathtaking Creekside Getaway★

Oct 7 – 14

$146 per night
Guest favorite

Apartment in Salem

4.97 out of 5 average rating, 147 reviews

Private rural retreat studio

May 15 – 22

$57 per night
Guest favorite

Home in New Albany

5.0 out of 5 average rating, 293 reviews

Welcome to the Bough House!

Aug 3 – 10

$91 per night
Guest favorite

Loft in Seymour

4.96 out of 5 average rating, 111 reviews

Spacious loft in downtown Seymour!

Feb 17 – 24

$69 per night
Guest favorite

Home in New Pekin

5.0 out of 5 average rating, 36 reviews

Country farm home

May 12 – 19

$116 per night
Guest favorite

Apartment in Charlestown

4.92 out of 5 average rating, 38 reviews

Cozy hideaway on Yankee creek.

Dec 28 – Jan 4

$88 per night
Guest favorite

Cottage in Floyds Knobs

5.0 out of 5 average rating, 66 reviews

Bright and Cheerful 1 Bedroom Cottage

Nov 20 – 27

$90 per night

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