Prestonville Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Prestonville

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (173)
"If you like a different kind of rental, rather remote, picturesque, quiet and private, this may be for you. 1800's cabin atmosphere with enough modern amenities to be very comfortable. A good "get away from it all" place."
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Peaceful getaway centrally located just min. from Madison and Belterra casino.

8.6 out of 10, Excellent, (12)
"Nice, quiet neighborhood in between Vevay and Madison."
Peaceful getaway centrally located just min. from Madison and Belterra casino.

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (26)
"Property and owner are great. Great stay (our 2nd time here). "
Carol’s Cabin in the Woods in Historic Hoosier Hills

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (34)
"I can’t say enough good things about our stay. Mona was just incredible and very kind and helpful. The house was so cozy and so clean. We had everything we needed and felt so at home during our stay. Mona even texted me before we arrived and asked if we’d like for her to put up the Christmas tree. Of course we said “YES”. It was just so sweet of her to ask. It added extra ambiance to an already beautiful home. It was the perfect place for me to bring my daughter to celebrate her 40th...
The Wadsworth in National Historic District of Madison, Indiana.

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (28)
"It was a nice cabin that is away from people so privacy is good. "
Rustic cabin just outside of Madison!

Cozy Cabin Madison Indiana

10.0 out of 10, Exceptional, (13)
"The cabin was great! It was clean and very well maintained! We loved the outdoor space and the location. Close to town, but out far enough that we could enjoy the quiet and the stars at night. The only thing we found challenging was the shower set up. Quite a step up to get in and the shower curtain was a little long and a little bit of a hazard. Otherwise we had everything we needed and we were very comfortable."
Cozy Cabin Madison Indiana

Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

10.0 out of 10, Exceptional, (206)
"The house was very clean and decorated nicely. Beautiful old river town. Wifi was spotty. This was only an issue in the evening when we wanted to watch a movie. That's my only complaint and for sure not a deal breaker. Great property. Would stay here again!"
Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

The Waterfall Suite Place + Walkout! Both Overlook Waterfall!

9.8 out of 10, Exceptional, (38)
"We had a lovely time at this property in Pendleton. It is located quite nicely between Louisville and Cincinnati. There were a few minor hiccups when we checked in, but Glenn was able to take care of those right away. The pool was a big hit with the kids. Overall, we highly recommend staying here!"
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (19)
"My twin sister and I visited for a birthday trip. Looked just like in the pictures and beds were very comfortable. Kitchen was fully stocked with cooking utensils, pans, salt and pepper, etc. Suzie thought of everything I didn't know we needed or wanted...from a cute birthday banner and piece of cake to milk or cream in the fridge for coffee. Will definitely stay again! Thanks for the hospitality. "
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Red comfy cottage

10.0 out of 10, Exceptional, (69)
"The home was fabulously clean, relaxing, and perfect for our small family. The location is not ideal as it is located between the Comfort Inn and a vehicle repair shop and is on the corner of two very busy/noisy roads. The front yard is literally the driveway between the two so smaller kids would not be able to go from the car to the house without an adult. However, the backyard was very private and the hot tub was the key to a wonderfully relaxing weekend. "
Red comfy cottage

THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA

9.8 out of 10, Exceptional, (44)
"Me and my whole family of 9 stayed here from out of state. It was a exactly as pictured and plenty of space. The teens enjoyed their own living space. The hot tub was warm and clean. We had a great time would definitely stay again if we ever visit the Louisville area again. "
THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (66)
"We loved this cabin. Everything was perfect. We'll definitely be coming back!"
Stoney Creek - Sit back and unwind

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

9.6 out of 10, Exceptional, (13)
"4 of us were coming to Madison area to celebrate our 50 year homecoming. The house allowed us to have more direct contact with each other than staying in a hotel and we enjoyed having a full kitchen and gathering space in the living areas. One bedrooms is very, very small with only a single bed in it and no other furniture. Might be OK for a child but renters need to be aware that there are only 3 full bedrooms in the house with one space to sleep an extra person."
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

KY log home close to The Ark Encounter on private 14 acres private seasonal pool

9.2 out of 10, Wonderful, (26)
"We enjoyed the space the cabin had to offer and had a great time."
KY log home close to The Ark Encounter on private 14 acres private seasonal pool

The Blue Door Place

10.0 out of 10, Exceptional, (5)
"The place is adorable and very comfortable. Things we especially appreciated were the super cute and tasteful decor, the fully stocked coffee bar (including travel cups & lids!), the front & back porch areas, location (lovely wooded winding drive leading to the property), and the FAST response from the host any time we had a question. I should also add the place was spotless. We fully enjoyed our stay and would not hesitate to come back!"
The price is AU$287
includes taxes & fees
1 Dec - 2 Dec
The Blue Door Place

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (40)
"This is a beautiful house and very well equipped. Alert - all the bedrooms are on the 2nd floor with is up 25 steps - straight up! The 2 bathrooms on the 2nd floor are not connected to any of the bedrooms and are right next to each other. So - unusual. Wonderful location- easy party - comfortable beds. We did put some of the breakable decorations in a safer place because of our little ones. We enjoyed our stay and would recommend this home. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

#207 King Suites, River Views, Deck, Downtown

10.0 out of 10, Exceptional, (27)
"Great location! Fabulous place to stay! Very clean with comforts of home. Walked to all our destinations during our 3 day visit."
The price is AU$894
includes taxes & fees
1 Dec - 2 Dec
#207 King Suites, River Views, Deck, Downtown

Livery Loft: our other BEST downtown location! Award winning! Come see why.

10.0 out of 10, Exceptional, (9)
"We really enjoyed our stay at Liverly Loft. Even though it rained, we had plenty things to do to keep us busy. This was one of the best VRBO I have ever stayed. Definitely will be back again... "
Livery Loft: our other BEST downtown location! Award winning! Come see why.

Waterfront - Near Ark Encounter

9.4 out of 10, Exceptional, (36)
"We enjoyed our stay here. The house is comfortable and tastefully decorated. Quiet neighborhood. My husband and daughter had a blast fishing. They caught and released at least a dozen catfish a piece. The walk down to the river pier is steep. Not something someone with mobility issues could do. We would stay again. "
Waterfront - Near Ark Encounter

Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit

10.0 out of 10, Exceptional, (47)
"This our third time staying here. It never gets old, treat yourself to a top notch Vrbo such as this one you will not regret it."
Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit
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.
Don't see what you're looking for?
See all available properties in Prestonville
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Prestonville you may be interested in

Belterra Casino Resort

3.5 star property
8.4 out of 10, Very good, (1001)
"Had a little trouble checking in, but it all worked out. Food was good. "
The price is AU$209
includes taxes & fees
2 Dec - 3 Dec
Belterra Casino Resort

Best Way Inn Madison

2.5 star property
6.8 out of 10, (450)
"Our TV was broken on arrival and they immediately replaced it even though it was getting late. Great attitudes of the staff."
The price is AU$119
includes taxes & fees
2 Dec - 3 Dec
Best Way Inn Madison

Ramada by Wyndham Sparta/At Speedway

2.5 star property
7.8 out of 10, Good, (1001)
"This was the first time in many years the hotel did not put the breakfast out early for the hunters. I have chosen to stay at the Sparta Ramada because they have made that single concession every other year. I and my other hunting friends that have stayed here for years may look elsewhere in the future. The staff was friendly and have been around for years. "
The price is AU$115
includes taxes & fees
22 Dec - 23 Dec
Ramada by Wyndham Sparta/At Speedway
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Prestonville?

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

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

Peaceful getaway centrally located just min. from Madison and Belterra casino.: This holiday home rental outside of Prestonville is located in a rural location, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What’s there to see and do in Prestonville?

Explore the area and family-friendly sights such as Madison Railroad Station Museum, or get out into nature at a spot like General Butler State Resort Park. In the wider area, you’ll find Historic District and Clifty Falls State Park.

What’s a holiday rental in Prestonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Prestonville. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for family trips.