Default HTG hotel image

Underwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Underwood vacation rentals

Terrace/patio

1. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (7 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
Cozy Tiny House in Scottsburg
1 bedroom, WiFi (free), bed sheets

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.
The price is SAR 504
SAR 1,165 total
includes taxes & fees
19 Aug - 20 Aug
Lakeside Cottage: 1 bed/1 bath
Coffee/tea maker, fridge, microwave, oven

3. 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, (42 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.
The price is SAR 558
SAR 953 total
includes taxes & fees
8 Aug - 9 Aug
Country home with beautiful views and access to hiking, biking, and horse trails
Coffee/tea maker, fridge, microwave, oven

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, (26 reviews)
"I can't say enough googd things about this Vrbo! CLEAN, great communication, great instructions on finding the place. My short stay showed the owners to be so nice. "
United States
Lynn R.
The price is SAR 357
SAR 594 total
includes taxes & fees
15 Aug - 16 Aug
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Smart TV

5. 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, (48 reviews)
"It was great to have easy parking and available garage. The home was very pet and kid friendly. Super close to Hanover. Will stay here many times over in the future for visits. "
United States
Abby E.
The price is SAR 436
SAR 933 total
includes taxes & fees
6 Aug - 7 Aug
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior

6. Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
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.
Lakeside Cabin: 4 bed/2.5 bath
Outdoor dining

7. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
10.0 out of 10, Exceptional, (17 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.
Modern cabin very close to scenic riverfront walks
Coffee/tea maker, fridge, microwave, oven

8. 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, (24 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is SAR 503
SAR 717 total
includes taxes & fees
24 Aug - 25 Aug
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Smart TV, books

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
10.0 out of 10, Exceptional, (2 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
The price is SAR 592
SAR 766 total
includes taxes & fees
11 Aug - 12 Aug
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
Property grounds

10. 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 SAR 541
SAR 1,167 total
includes taxes & fees
1 Sep - 2 Sep
River Retreat
Property grounds

11. 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 SAR 606
SAR 1,228 total
includes taxes & fees
6 Aug - 7 Aug
King Bedroom, Outdoor Cabana w/ Bed Swing, Quiet House Minutes to D/T Louisville
Property grounds

12. 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, (9 reviews)
"Beautiful home & I would highly recommend staying there👍👍"
United States
Kenneth
The price is SAR 673
SAR 1,325 total
includes taxes & fees
18 Aug - 19 Aug
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Terrace/patio

13. Spacious family cabin with game room and backyard!

Spacious family cabin with game room and backyard!
Hanover
10.0 out of 10, Exceptional, (1 review)
"This was a wonderful place to stay! Quiet and peaceful, host were awesome if we had any questions. A very pleasant experience!"
United States
Marvin D.
The price is SAR 927
SAR 2,401 total
includes taxes & fees
3 Sep - 4 Sep
Spacious family cabin with game room and backyard!
Microwave, oven, stovetop, dishwasher

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

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Hanover
9.2 out of 10, Wonderful, (5 reviews)
"It was lovely!"
United States
Carolyne R.
The price is SAR 841
SAR 1,883 total
includes taxes & fees
3 Sep - 4 Sep
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Outdoor dining

15. T&E Riverhouse Retreat

T&E Riverhouse Retreat
Hanover
10.0 out of 10, Exceptional, (11 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 SAR 859
SAR 1,580 total
includes taxes & fees
2 Sep - 3 Sep
T&E Riverhouse Retreat
Smart TV, fireplace, books

16. 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, (9 reviews)
"This place is awesome! We were in for the derby and it’s a perfect location in a quiet neighborhood! Beautiful river in the back. Clean, plenty of linens, fully stocked kitchen! "
United States
Lori F.
The price is SAR 1,393
SAR 2,666 total
includes taxes & fees
3 Sep - 4 Sep
The Barge Inn: Your Epic Ohio River Waterfront Escape in Beautiful Prospect, KY!
Terrace/patio

17. 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 SAR 2,667
SAR 6,060 total
includes taxes & fees
9 Aug - 10 Aug
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Underwood Hotel Reviews

Hampton Inn & Suites Scottsburg

Hampton Inn & Suites Scottsburg

10/10 Excellent
"The property was very clean, as were the rooms. Breakfast was very good. Staff was wonderful, epically Matt and the breakfast person."
Nancy 1-night trip
Posted 11 hours ago
Hampton Inn & Suites Scottsburg

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?

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!: This vacation home rental outside of Underwood offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.