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Henry County Vacation Rentals

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Our top choices for Henry County vacation rentals

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.
The price is CA $278
CA $736 total
includes taxes & fees
Nov 18 - Nov 19
Updated 3 bed, 2.5 bath 1,900 sq ft home

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.
The price is CA $228
CA $787 total
includes taxes & fees
Nov 16 - Nov 17
Kentucky Bourbon Trail: Hot Tub & Game Room

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.
The price is CA $136
CA $249 total
includes taxes & fees
Nov 30 - Dec 1
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

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.
The price is CA $666
CA $804 total
includes taxes & fees
Nov 30 - Dec 1
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+

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.
The price is CA $128
CA $241 total
includes taxes & fees
Nov 18 - Nov 19
Unique Downtown Studio with an Industrial Vibe

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.
The price is CA $203
CA $392 total
includes taxes & fees
Nov 19 - Nov 20
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

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.
The price is CA $200
CA $379 total
includes taxes & fees
Nov 16 - Nov 17
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

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.
The price is CA $384
CA $631 total
includes taxes & fees
Nov 22 - Nov 23
The Sweet Retreat Wheelchair Accessible Historic Home

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.
The price is CA $127
CA $159 total
includes taxes & fees
Nov 17 - Nov 18
Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail

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
The price is CA $127
CA $158 total
includes taxes & fees
Nov 21 - Nov 22
StudioRes by Marriott Louisville East

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.
The price is CA $357
CA $1,422 total
includes taxes & fees
Dec 2 - Dec 3
Estate: Heated Pool, Hot Tub, Game Rooms, Pets

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.
The price is CA $266
CA $679 total
includes taxes & fees
Nov 29 - Nov 30
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

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.
The price is CA $315
CA $604 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful restored Victorian farmhouse

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.
The price is CA $474
CA $1,250 total
includes taxes & fees
Nov 16 - Nov 17
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS

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.
The price is CA $173
CA $314 total
includes taxes & fees
Nov 16 - Nov 17
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

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
The price is CA $127
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

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.
The price is CA $109
CA $139 total
includes taxes & fees
Nov 16 - Nov 17
Vintage Camper Cabin on Beautiful Farm Near Ark & Bourbon Trail

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.
The price is CA $100
CA $222 total
includes taxes & fees
Nov 16 - Nov 17
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

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.
The price is CA $197
CA $377 total
includes taxes & fees
Nov 16 - Nov 17
Scenic Highgrounds Modern Cabin - Chicory

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.
The price is CA $143
CA $232 total
includes taxes & fees
Nov 16 - Nov 17
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

Find out more about Henry County

Everything you need to know about Henry County 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 Henry County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Henry County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Henry County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Henry County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Henry County vacation rentals we have selected for you start as low as CA $107 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Henry County rentals

At Expedia, we put the best Henry County 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 Henry County 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 Henry County 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 Henry County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.