Henryville Holiday Rentals

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Our top choices for Henryville holiday rentals

Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
Henryville
The price is NZ$1,011
includes taxes & fees
24 Feb - 25 Feb
Lakeside Cabin: 4 bed/2.5 bath

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.6 out of 10, Exceptional, (39 reviews)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is NZ$412
includes taxes & fees
1 Mar - 2 Mar
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (10 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is NZ$240
includes taxes & fees
24 Feb - 25 Feb
Alfesco - Walkable Highlands Guesthouse

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (53 reviews)
"We loved our stay at this cottage. Very quiet and relaxing. We will definitely stay here again!"
United States
Jarrod H.
The price is NZ$395
includes taxes & fees
24 Feb - 25 Feb
Carriage House, 7 minutes from downtown Louisville

Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!
3.0 star property
New Albany
10.0 out of 10, Exceptional, (1 review)
"Amy was wonderful and went above and beyond to make sure we had a great stay. She even left pancakes w/syrup for breakfast and pasta w/sauce in case we didn’t have time to go to the store! It’s the small things that really stick out such as leaving a bowl of snacks, a few beers in the fridge, a bottle of wine, fully stocked medicine cabinet in case you forgot something. She even put food and water out for the dog along with toys and a blanket! We loved being there and it was such a beautiful...
United States
Robin
The price is NZ$576
includes taxes & fees
25 Feb - 26 Feb
Home w/ Fenced Backyard, 6 Mi to Dtwn Louisville!

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
8.8 out of 10, Excellent, (37 reviews)
"Clean room, history and location. "
United States
RICHARD
The price is NZ$221
includes taxes & fees
1 Mar - 2 Mar
The Bellwether Hotel

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (14 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is NZ$246
includes taxes & fees
24 Feb - 25 Feb
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming house in one of Louisville's most coveted neighborhoods

Charming house in one of Louisville's most coveted neighborhoods
Louisville
10.0 out of 10, Exceptional, (78 reviews)
"Great location, very clean!!!!"
United States
Matt W.
The price is NZ$511
includes taxes & fees
25 Feb - 26 Feb
Charming house in one of Louisville's most coveted neighborhoods

The Duke Hotel

The Duke Hotel
2.0 star property
Downtown Louisville
10.0 out of 10, Exceptional, (1 review)
"Great stay! Clean and very easy to acess. "
United States
Justin
The price is NZ$235
includes taxes & fees
25 Feb - 26 Feb
The Duke Hotel

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
8.8 out of 10, Excellent, (8 reviews)
"Stayed for a friends wedding at Whitehall. Location was great and we were able to walk to a handful of restaurants and coffee shops "
United States
Natalie H.
The price is NZ$440
includes taxes & fees
4 Mar - 5 Mar
St. Matthew’s - Walk to Shops & Restaurants

Beloved Home w/Priv Parking. BOOK for MATS, DERBY!

Beloved Home w/Priv Parking. BOOK for MATS, DERBY!
Germantown
10.0 out of 10, Exceptional, (72 reviews)
"Super nice spot just perfect for two "
United States
Rick R.
The price is NZ$343
includes taxes & fees
24 Feb - 25 Feb
Beloved Home w/Priv Parking. BOOK for MATS, DERBY!

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (7 reviews)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is NZ$295
includes taxes & fees
24 Feb - 25 Feb
Cozy Tiny House in Scottsburg

Cozy Tree-Lined Carriage Home - Stay in Serenity!

Cozy Tree-Lined Carriage Home - Stay in Serenity!
Louisville
9.8 out of 10, Exceptional, (24 reviews)
"Great place "
United States
Scott L.
The price is NZ$268
includes taxes & fees
4 Mar - 5 Mar
Cozy Tree-Lined Carriage Home - Stay in Serenity!

Germantown Fav! BOOK for MATS, DERBY 2026!

Germantown Fav! BOOK for MATS, DERBY 2026!
Germantown
10.0 out of 10, Exceptional, (72 reviews)
"Cute comfortable house would go again"
United States
Hope N.
The price is NZ$343
includes taxes & fees
26 Feb - 27 Feb
Germantown Fav! BOOK for MATS, DERBY 2026!

March Deal, Karaoke, 5 Kings, Hot Tub, 2 Game Rms

March Deal, Karaoke, 5 Kings, Hot Tub, 2 Game Rms
La Grange
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay!"
United States
Katie H.
The price is NZ$1,202
includes taxes & fees
2 Mar - 3 Mar
March Deal, Karaoke, 5 Kings, Hot Tub, 2 Game Rms

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
New Albany
10.0 out of 10, Exceptional, (38 reviews)
"Nice place"
United States
Amanda C.
The price is NZ$331
includes taxes & fees
24 Feb - 25 Feb
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
Jeffersonville
9.6 out of 10, Exceptional, (15 reviews)
"Great weekend spot simple clean great communicator open for constructive feedback. Were would choose this place again"
United States
Anonymous traveller
The price is NZ$490
includes taxes & fees
24 Feb - 25 Feb
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (83 reviews)
"Great host beautiful house "
United States
Shantej G.
The price is NZ$532
includes taxes & fees
25 Feb - 26 Feb
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Crescent Hill
10.0 out of 10, Exceptional, (118 reviews)
"Host met onsite, informed of details and was friendly and helpful. Good location and nicely remodeled older home w lots of updates. Would stay again. "
United States
Dale K.
The price is NZ$394
includes taxes & fees
24 Feb - 25 Feb
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Clifton
10.0 out of 10, Exceptional, (31 reviews)
"Our stay was very pleasant, great location, lots of great restaurants. Tyler the host was was always available when we had an issue. "
United States
Max D.
The price is NZ$291
includes taxes & fees
1 Mar - 2 Mar
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
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 Henryville Hotel Reviews

Find out more about Henryville

Everything you need to know about Henryville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Henryville holiday rental for you. At Expedia, you can take your pick from private holiday 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 Henryville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Henryville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Henryville. 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 Henryville holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Henryville holiday rentals we have selected for you start as low as NZ$221 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Henryville rentals

At Expedia, we put the best Henryville holiday 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 Henryville 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 Henryville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Henryville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Henryville?

Yes, there are holiday rentals close to the most popular sights in Henryville, or you can select a more secluded option if you're looking for a relaxing stay. Henryville is known for its golf courses.

What are some of the best holiday rentals that Henryville has to offer?

Charming home in the heart of the city!: This holiday home rental outside of Henryville is equipped with a selection of games, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Henryville?

Explore the area and family-friendly sights such as Charlestown Family Activities Park, or get out into nature at a spot like Deam Lake State Recreation Area. Champions Pointe Golf Club and White Oak Nature Preserve are other places to visit while you're in town.

What’s a holiday rental in Henryville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Henryville. Holiday rentals provide amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips or small group gatherings.