Underwood Vacation Rentals

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Check prices for these dates

Our top choices for Underwood vacation rentals

1. 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, (30 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
The price is SARĀ 394
SARĀ 539 total
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

2. 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, (32 reviews)
"Great host and a great location!"
United States
P a.
The price is SARĀ 394
SARĀ 606 total
includes taxes & fees
7 Dec - 8 Dec
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

3. Tiny Lakeside Cottage I 50 Acres of Gardens

Tiny Lakeside Cottage I 50 Acres of Gardens
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.
The price is SARĀ 524
SARĀ 1,133 total
includes taxes & fees
14 Nov - 15 Nov
Tiny Lakeside Cottage I 50 Acres of Gardens

4. 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.
The price is SARĀ 174
SARĀ 874 total
includes taxes & fees
7 Dec - 8 Dec
Modern cabin very close to scenic riverfront walks

5. 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, (44 reviews)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is SARĀ 619
SARĀ 1,021 total
includes taxes & fees
16 Nov - 17 Nov
Country home with beautiful views and access to hiking, biking, and horse trails

6. Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Henryville
10.0 out of 10, Exceptional, (176 reviews)
"Great host, clean house in a great location. We really enjoyed our stay."
United States
Michael S.
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

7. 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.
The price is SARĀ 465
SARĀ 1,035 total
includes taxes & fees
24 Nov - 25 Nov
River Retreat

8. Enchanting Lakeside Cabin I 50 Acres of Gardens

Enchanting Lakeside Cabin I 50 Acres of Gardens
Henryville
8.0 out of 10, Very good, (3 reviews)
"The most beautiful and peaceful place we have ever stayed!! It was neat to find out the history and if you have the chance to stay here, DO NOT MISS IT!! if I could have stayed forever I would have. I was sad to leave! Just a very special place!! I’ve stayed in a LOT of different places and none compares!! It was an honor & our dogs absolutely loved the place!! Never seen them so happy and comfortable in a place!!"
United States
Melanie G.
The price is SARĀ 1,625
SARĀ 2,987 total
includes taxes & fees
24 Nov - 25 Nov
Enchanting Lakeside Cabin I 50 Acres of Gardens

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

Family-friendly cabin with game room and backyard!
Hanover
10.0 out of 10, Exceptional, (5 reviews)
"This property is unbelievably clean and had so many amenities that the stay was fabulous, enjoyable, and exactly what we were hoping for. Such a great place!!"
United States
Lauren N.
The price is SARĀ 522
SARĀ 1,920 total
includes taxes & fees
7 Dec - 8 Dec
Family-friendly cabin with game room and backyard!

10. 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, (55 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The price is SARĀ 490
SARĀ 965 total
includes taxes & fees
18 Nov - 19 Nov
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

11. The Secluded Woodland Retreat | Cabin + Cottage

The Secluded Woodland Retreat | Cabin + Cottage
Henryville
The price is SARĀ 1,907
SARĀ 4,081 total
includes taxes & fees
7 Dec - 8 Dec
The Secluded Woodland Retreat | Cabin + Cottage

12. 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, (10 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
The price is SARĀ 591
SARĀ 727 total
includes taxes & fees
14 Nov - 15 Nov
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

13. 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
9.8 out of 10, Exceptional, (12 reviews)
"We loved our stay here. It was the perfect location. The house was clean and I would stay here again."
United States
Nina L.
The price is SARĀ 627
SARĀ 1,211 total
includes taxes & fees
30 Nov - 1 Dec
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

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

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.4 out of 10, Exceptional, (8 reviews)
"It was lovely!"
United States
Carolyne R.
The price is SARĀ 760
SARĀ 1,698 total
includes taxes & fees
22 Nov - 23 Nov
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

15. 10 Min to Louisville, Huge Hot Tub, Awesome Backyard

10 Min to Louisville, Huge Hot Tub, Awesome Backyard
Clarksville
10.0 out of 10, Exceptional, (63 reviews)
"House was very nice. Perfect spot!"
United States
Madison H.
10 Min to Louisville, Huge Hot Tub, Awesome Backyard

16. 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
The price is SARĀ 639
SARĀ 1,309 total
includes taxes & fees
7 Dec - 8 Dec
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville

17. 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.
The price is SARĀ 1,554
SARĀ 2,743 total
includes taxes & fees
7 Dec - 8 Dec
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!

18. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful view of the river! Nice location and easy to find. Highly recommend for a group getaway. "
United States
Beverly L.
The price is SARĀ 859
SARĀ 1,544 total
includes taxes & fees
30 Nov - 1 Dec
T&E Riverhouse Retreat

19. 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.
The price is SARĀ 3,540
SARĀ 6,812 total
includes taxes & fees
30 Nov - 1 Dec
Star Ridge | Private Estate | Sleeps 20 | Hot Tub

20. 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.
The price is SARĀ 742
SARĀ 2,737 total
includes taxes & fees
7 Dec - 8 Dec
Spacious family cabin with game room and backyard!
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.

Find vacation rentals that suit your style

Top Underwood Hotel Reviews

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.