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Underwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Underwood vacation rentals

A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

1. Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
9.8 out of 10, Exceptional, (43 reviews)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
$257 nightly
The price is $288
Oct 17 - Oct 18
Total with taxes and fees
Country home with beautiful views and access to hiking, biking, and horse trails
A room with a bed, two armchairs, a small table, and a microwave.

2. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
$264 nightly
The price is $308
Oct 14 - Oct 15
Total with taxes and fees
Lakeside Cottage: 1 bed/1 bath
A covered patio with a door, two wicker chairs, and string lights.

3. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
$183 nightly
The price is $205
Oct 24 - Oct 25
Total with taxes and fees
Cozy Tiny House in Scottsburg
A compact kitchen with a refrigerator, microwave, stove, and sink. There is a dining table with chairs and a patterned rug.

4. Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Memphis
10.0 out of 10, Exceptional, (28 reviews)
"Great host and a great location!"
United States
P a.
$149 nightly
The price is $168
Oct 29 - Oct 30
Total with taxes and fees
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

5. 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, (26 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
$145 nightly
The price is $164
Oct 20 - Oct 21
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A house with a large garage, a dock, and a river.

6. River Retreat

River Retreat
Charlestown
10.0 out of 10, Exceptional, (1 review)
"Easy check in. Nice cozy home right by the river. Even left a golf cart for use when staying!"
United States
Brady S.
$255 nightly
The price is $288
Oct 14 - Oct 15
Total with taxes and fees
River Retreat
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

7. 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, (53 reviews)
"Close to downtown Madison and Clifty Falls, this place had everything we needed to visit the area and relax I'm the evening."
United States
Maggie D.
$235 nightly
The price is $270
Oct 22 - Oct 23
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A white bedroom with a large bed, a wooden nightstand, and a wall-mounted lamp.

8. Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden

Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
Henryville
$980 nightly
The price is $1,141
Nov 9 - Nov 10
Total with taxes and fees
Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
A rustic cabin interior with a stone fireplace, wooden beams, a green sofa, and a television.

9. Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
Floyd knobs
9.0 out of 10, Wonderful, (8 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
$181 nightly
The price is $204
Oct 14 - Oct 15
Total with taxes and fees
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
A brick building with a central entrance, a small porch, and a pathway leading to the entrance.

10. The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Salem
9.6 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay at the Lanning house. It was a very clean and comfortable place to stay. We enjoyed the history of the home as well."
United States
Andrew H.
$285 nightly
The price is $319
Oct 14 - Oct 15
Total with taxes and fees
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
A spacious living room with a large sofa, a coffee table, and a TV. There is a balcony with a view of a lake.

11. The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!

The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
Prospect
9.8 out of 10, Exceptional, (10 reviews)
"My family and I had a wonderful trip. The house was absolutely beautiful. Everything was clean and well taken care of we couldn’t have asked for a better vacation"
United States
Thomas c.
$585 nightly
The price is $645
Oct 14 - Oct 15
Total with taxes and fees
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
A kitchen with a central island, wooden stools, a trash bin, and a hanging plant arrangement.

12. The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.2 out of 10, Wonderful, (7 reviews)
"It was lovely!"
United States
Carolyne R.
$411 nightly
The price is $472
Oct 18 - Oct 19
Total with taxes and fees
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
A wooden swing bed with a pergola roof, string lights, and a wooden deck.

13. 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, (17 reviews)
"The property was very nice for our family getaway, would book again."
United States
Roberta
$381 nightly
The price is $387
Oct 29 - Oct 30
Total with taxes and fees
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
A log cabin interior with a living area featuring a sofa and a dining table with chairs.

14. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.4 out of 10, Exceptional, (20 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
$204 nightly
The price is $220
Oct 26 - Oct 27
Total with taxes and fees
Modern cabin very close to scenic riverfront walks
A log cabin with a fire pit and outdoor seating.

15. Family-friendly cabin with game room and backyard!

Family-friendly cabin with game room and backyard!
Hanover
10.0 out of 10, Exceptional, (4 reviews)
"Host is very easy to communicate with and the property provided us with great memories! Would definitely stay here again!"
United States
Eli H.
$399 nightly
The price is $431
Nov 4 - Nov 5
Total with taxes and fees
Family-friendly cabin with game room and backyard!
A covered outdoor deck with a table and chairs, a ceiling fan, and a view of a body of water.

16. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
10.0 out of 10, Exceptional, (13 reviews)
"Located in a quiet area with great river views. Well stocked kitchen. Would stay there again"
United States
Phil T.
$374 nightly
The price is $422
Nov 2 - Nov 3
Total with taxes and fees
T&E Riverhouse Retreat
A log cabin with a fire pit and outdoor seating.

17. Spacious family cabin with game room and backyard!

Spacious family cabin with game room and backyard!
Hanover
9.4 out of 10, Exceptional, (3 reviews)
"Property is beautiful"
United States
Barb N.
$574 nightly
The price is $620
Oct 26 - Oct 27
Total with taxes and fees
Spacious family cabin with game room and backyard!
A large house with a covered patio area featuring outdoor seating and a fire pit.

18. Star Ridge | Private Estate | Sleeps 20 | Hot Tub

Star Ridge | Private Estate | Sleeps 20 | Hot Tub
Wood Township
10.0 out of 10, Exceptional, (8 reviews)
"Really great to have our annual family reunion here for the second time! Such a great place for multigenerational fun! John is a wonderful host!"
United States
martha u.
$1,746 nightly
The price is $1,895
Oct 26 - Oct 27
Total with taxes and fees
Star Ridge | Private Estate | Sleeps 20 | Hot Tub
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 Underwood Hotel Reviews

HavenPointe Inn & Suites

HavenPointe Inn & Suites

10/10 Excellent
"This was a very clean Hotel. The lobby, breakfast area and meeting room were all very clean. The room looked newly remodeled. I don't know if they were but they were meticulously cleaned. This was an exceptional stay for us and at the price I paid it made it even better. The waffle maker at breakfast made an awesome waffle! Thank You Havenpointe Inn for making us feel so welcome! Jeff M."
Jeff 1-night trip
Posted 2 hours ago
HavenPointe Inn & Suites

Find out more about Underwood

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

Underwood vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Underwood rentals

At Expedia, we put the best Underwood 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 Underwood 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 Underwood 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 Underwood. 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

Are there vacation rentals in Underwood?

Yes, we offer vacation rentals close to well known sights in Underwood, or you can choose a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Underwood?

10 Min to Louisville, Huge Hot Tub, Awesome Backyard: This vacation home rental outside of Underwood is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

What can I see and do in Underwood?

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 Covered Bridge Golf Club are a couple of places you'll find in the larger area.

What are vacation rentals like in Underwood?

Vacation rentals are private properties you can reserve for several days or longer in Underwood. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip.