Vacation Rentals in Henry County

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Top cities in Henry County

A field of purple thistles with a sunset in the background.
Vacation Rentals

Eminence

Eminence

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 Henry County vacation rentals

A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

1. Updated 3 bed, 2.5 bath 1,900 sq ft home

Updated 3 bed, 2.5 bath 1,900 sq ft home
La Grange
10.0 out of 10, Exceptional, (11 reviews)
"Very nice house, spacious, clean and very comfortable. Perfect for our stay to attend a conference in the area. Highly recommend!!"
United States
Jessica B.
$452 nightly
The price is $511
Nov 16 - Nov 17
Total with taxes and fees
Updated 3 bed, 2.5 bath 1,900 sq ft home
A bedroom with a large bed, two bedside lamps, a window with curtains, and a ceiling fan.

2. Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (26 reviews)
"Such a beautiful, peaceful area and the cutest home! It was perfect for our large group and Iris was an incredible host. We definitely want to visit again!"
United States
Hannah G.
$497 nightly
The price is $551
Nov 16 - Nov 17
Total with taxes and fees
Kentucky Bourbon Trail: Hot Tub & Game Room
A kitchen with a gas stove, a coffee maker, and built-in ovens.

3. Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (22 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
$157 nightly
The price is $174
Nov 30 - Dec 1
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A log cabin with a covered porch, large windows, and a well-maintained front yard.

4. The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
Shelbyville
10.0 out of 10, Exceptional, (12 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
$506 nightly
The price is $564
Nov 30 - Dec 1
Total with taxes and fees
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
A bar area with stools, a coffee machine, and a large metal horseshoe decoration on the wall.

5. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful location in a very nice small town. Grocery store, coffee shop and many other amenities close by.The property was very spacious and well done for 2 people."
United States
Kathleen S.
$152 nightly
The price is $169
Nov 18 - Nov 19
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

6. Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville
9.4 out of 10, Exceptional, (51 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
$235 nightly
The price is $262
Nov 17 - Nov 18
Total with taxes and fees
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A modern cabin with a wooden deck and a balcony, surrounded by a natural landscape.

7. Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Frankfort
9.6 out of 10, Exceptional, (26 reviews)
"What a great cabin it was so clean and cute and had everything that we needed a great place to stay"
United States
Jessica S.
$234 nightly
The price is $265
Nov 16 - Nov 17
Total with taxes and fees
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
A wooden deck with a green door, wicker chairs, and a small table.

8. The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (7 reviews)
"I loved having the travel crib and high chair available for my kids! Everything was clean and the host made everything a breeze!"
United States
Samantha C.
$387 nightly
The price is $439
Nov 22 - Nov 23
Total with taxes and fees
The Sweet Retreat Wheelchair Accessible Historic Home
A cozy room with a large window, a wooden table with a blanket and a notebook, and a red pillow.

9. Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail

Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail
Owenton
9.4 out of 10, Exceptional, (92 reviews)
"Such a great stay & getaway with my pups! The property is so nice and cozy for what we needed! Wonderful and helpful host too! We’ll be back "
United States
Mary S.
$101 nightly
The price is $111
Nov 17 - Nov 18
Total with taxes and fees
Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail
A multi-story building with a 'STUDIORES' sign, featuring a modern facade with evenly spaced windows and a flat roof.

10. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
7.6 out of 10, Good, (18 reviews)
"Clean hotel, very helpful staff."
United States
Christopher
$94 nightly
The price is $111
Nov 22 - Nov 23
Total with taxes and fees
StudioRes by Marriott Louisville East
A spacious dining area with a large table set for six, surrounded by modern chairs. A chandelier hangs from the ceiling, and a staircase leads to an upper level. The kitchen in the background features white cabinets and a central island.

11. Estate: Heated Pool, Hot Tub, Game Rooms, Pets

Estate: Heated Pool, Hot Tub, Game Rooms, Pets
La Grange
10.0 out of 10, Exceptional, (29 reviews)
"We had a wonderful stay!"
United States
Katie H.
$902 nightly
The price is $990
Dec 2 - Dec 3
Total with taxes and fees
Estate: Heated Pool, Hot Tub, Game Rooms, Pets
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

12. Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
9.8 out of 10, Exceptional, (30 reviews)
"Our stay at"
United States
Sarah F.
$418 nightly
The price is $474
Nov 16 - Nov 17
Total with taxes and fees
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

13. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (16 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
$381 nightly
The price is $424
Nov 16 - Nov 17
Total with taxes and fees
Beautiful restored Victorian farmhouse
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

14. *NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS

*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
Bagdad
9.8 out of 10, Exceptional, (11 reviews)
"My family & I had a great time at the house. My grandkids loved the pool. It was a very enjoyable stay."
United States
LORI T.
$795 nightly
The price is $876
Nov 16 - Nov 17
Total with taxes and fees
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

15. The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (53 reviews)
"Had a very nice stay"
United States
Brad P.
$193 nightly
The price is $221
Nov 16 - Nov 17
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Property grounds

16. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.4 out of 10, Exceptional, (20 reviews)
"Clean and cozy"
United States
Julie
$141 nightly
The price is $162
Nov 16 - Nov 17
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A gravel path leading to a red barn with a white roof, surrounded by grass and trees.

17. Vintage Camper Cabin on Beautiful Farm Near Ark & Bourbon Trail

Vintage Camper Cabin on Beautiful Farm Near Ark & Bourbon Trail
Owenton
9.4 out of 10, Exceptional, (18 reviews)
"If you’re looking for a quiet place to relax this is it. Josh was so pleasant to work with."
United States
Teresa I.
$89 nightly
The price is $98
Nov 16 - Nov 17
Total with taxes and fees
Vintage Camper Cabin on Beautiful Farm Near Ark & Bourbon Trail
A modern living room with a TV mounted on the wall, a wooden console table, a floor lamp, a potted plant, and a basket.

18. Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
Frankfort
8.8 out of 10, Excellent, (92 reviews)
"It was a nice stay"
United States
Teresa M.
$132 nightly
The price is $155
Nov 16 - Nov 17
Total with taxes and fees
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
A modern cabin with a wooden deck, a covered outdoor seating area, and a bright orange door.

19. Scenic Highgrounds Modern Cabin - Chicory

Scenic Highgrounds Modern Cabin - Chicory
Frankfort
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay, beautiful scenery! just far enough out of the city! Would definitely stay there again."
United States
Rob L.
$246 nightly
The price is $264
Nov 16 - Nov 17
Total with taxes and fees
Scenic Highgrounds Modern Cabin - Chicory
Two wooden cabins labeled 'Maple' and 'Sassafras' in a forested campground with gravel paths.

20. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (17 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
$140 nightly
The price is $163
Nov 16 - Nov 17
Total with taxes and fees
Maple Cozy Cabin at Lost Trails
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 Henry County Hotel Reviews

A lobby with a wooden ceiling, a beige sofa, two armchairs, a patterned rug, and a reception desk.
Holiday Inn Express & Suites La Grange by IHG

Holiday Inn Express & Suites La Grange by IHG

Holiday Inn Express & Suites La Grange by IHG
La Grange

10/10 Excellent

The Hotel was nice and the staff was nice. The room was O.K. The carpet in the room had a big stain next to the bed.
United States
Larry
Reviewed June 26, 2023
Holiday Inn Express & Suites La Grange by IHG

Frequently Asked Questions

How many vacation rentals are available in Henry County?

Expedia has plenty of vacation rentals to choose from in and around Henry County, so you’re guaranteed to find the right one for you.


How much is a vacation rental in Henry County?

The selection of Henry County vacation rentals we have selected for you start as low as $97 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Henry County?

Vacation rentals in Henry County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Henry County vacation rentals to suit everyone.


Why should I choose a vacation rental in Henry County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Henry County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.


How do I find the best deal on a vacation rental in Henry County?

Find vacation rentals in Henry County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Henry County.


What amenities are available in a vacation rental in Henry County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Henry County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Henry County?

Everytime is a great time to head to Henry County! Staying in a Henry County vacation rentals you will always find lots going on to keep you entertained.


Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Henry County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Henry County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Henry County, you can save even more.


Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Henry County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.