Prestonville Holiday Rentals

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Holiday Rentals in Prestonville

1800’s restored log cabin on 26 private rolling wooded acres with sunset views
10.0 out of 10, Exceptional, (150)
"This is our 3rd year staying at the cabin. We love it! Best place to relax and get grounded."
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
The Cozy Cottage on Main
9.2 out of 10, Wonderful, (49)
"Cottage was so nice and decorated so cute. It was great for what we wanted to do,SHOP, so close to all the shops and restaurants. I hope we get the chance to stay there again! Jan and Kelly"
The price is NZ$352
includes taxes & fees
3 Jun - 4 Jun
The Cozy Cottage on Main
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
9.8 out of 10, Exceptional, (36)
"We've joined together for Thanksgiving for several years and this was by far the nicest place. My only complaint would be the ice maker didn't work. We hope to visit again!"
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
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Rustic cabin just outside of Madison!
10.0 out of 10, Exceptional, (13)
"It was an adventure crossing the creek after a lot of rain, but we made it! There was plenty of room for our family of 11. The host was very attentive to our needs. Not every family member was prepared for the rusticness, but we had a great time nonetheless. The area is just gorgeous!"
Rustic cabin just outside of Madison!
Stoney Creek - Sit back and unwind
10.0 out of 10, Exceptional, (59)
""When can I move in?" This property was my personal heaven on earth dream home. I spent four days of no worries, relaxation, and comfort in this cabin. Close to Madison and Clifty Falls State Park if you really want and/or need to leave, but why? ;-)"
Stoney Creek - Sit back and unwind
River Views from Every Room! Clean, Newly Remodeled, Full Kitchen
9.8 out of 10, Exceptional, (52)
"2 days of rest"
River Views from Every Room! Clean, Newly Remodeled, Full Kitchen
The Wadsworth in National Historic District of Madison, Indiana.
10.0 out of 10, Exceptional, (17)
"Great home. Near everything. Very clean. Mona was extremely helpful."
The Wadsworth in National Historic District of Madison, Indiana.
Tiny Too (Tiny house w/ River View)
10.0 out of 10, Exceptional, (116)
"Very nice. Enjoyed the river, the town, the state park."
Tiny Too (Tiny house w/ River View)
Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River
10.0 out of 10, Exceptional, (190)
"Very clean. Comfy beds. Close to Clifty Falls. Enjoyed our getaway!"
Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River
THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA
9.8 out of 10, Exceptional, (42)
"Nice little get away, hosts were great, the house was adequate for what we needed."
THE WATERFALL WALKOUT & HILLTOP RETREAT, SLEEPS 10+, 4BR*2BA
Waterfront - Near Ark Encounter
9.6 out of 10, Exceptional, (34)
"Great house on the creek. Dock was awesome."
Waterfront - Near Ark Encounter
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
8.8 out of 10, Excellent, (17)
"We had a great time staying at this cabin with my brother and his family! The kitchen had everything we needed to cook lots of meals together, and having two full bathrooms was just right for our two families. The property was well-maintained and fun to explore. Our kids especially loved the game room in the basement! I did dock one star from the "accuracy of online listing" section because the listing specifically states that there are four bedrooms (1 with 2 queens, 2 with 1 queen each, and 1...
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Secluded Country Home in Historic Hoosier Hills
10.0 out of 10, Exceptional, (107)
"This place was by far the best place we have stayed at. It was so well stocked. Thank you so much for allowing us to stay."
Secluded Country Home in Historic Hoosier Hills
2 King Suites, 2 Queens, 3.5 Ba, River Views, Deck. Bicentennial Park 209
10.0 out of 10, Exceptional, (39)
"Beautiful home with well equiped kitchen. 4 bedrooms so we each had our own. Close to everything and the river."
The price is NZ$906
includes taxes & fees
27 Jun - 28 Jun
2 King Suites, 2 Queens, 3.5 Ba, River Views, Deck. Bicentennial Park 209
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
10.0 out of 10, Exceptional, (4)
"This property is amazing. The owner helped make our stay enjoyable and relaxing."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Red comfy cottage
10.0 out of 10, Exceptional, (62)
"The house was as advertised, very quiet, clean, and the owner was very good about communicating. We will be back to stay again in the future."
Red comfy cottage
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
10.0 out of 10, Exceptional, (111)
"The house was great. Very clean. Spacious. Had everything you could need. No TVs in the bedrooms which we were disappointed about. Check in was not a good process. App said the code to enter was last 4 digits of my number and it wasn't. I called and messaged the lady on Vrbo and no response. The lady next door had noticed we were trying to get in and said she was now managing the property and gave me the code and we got in. Later that code didnt work and it somehow was now switched to my last 4...
The price is NZ$396
includes taxes & fees
30 Jun - 1 Jul
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
East Main Lofts -Roller Rink 301
The price is NZ$1,136
includes taxes & fees
30 Jun - 1 Jul
East Main Lofts -Roller Rink 301
The Blue Door Place
10.0 out of 10, Exceptional, (1)
"Great place. Very cute. Decorated nicely. Very clean. We would have no problem staying here again."
The price is NZ$301
includes taxes & fees
2 Jun - 3 Jun
The Blue Door Place
Cozy Cabin Madison Indiana
10.0 out of 10, Exceptional, (4)
"Nice and private. Nice yard and fire pit. Very clean. The pullout bed is rough sleeping...be nicer if some kind of thin rollout foam cushion to throw on top. Upstairs bed is comfy with low ceiling. Didn't have any dish soap left, no chocolate for s'mores (was in ad or wouldn't mention). No wood for fire. We purchased those 3 items and was too windy to have a fire sadly 😥. On the whole we were very happy and had a nice time. Host was great!"
Cozy Cabin Madison Indiana
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See all available properties in Prestonville
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.

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, (1004)
"Everything is very clean, the property is showing some age on the exterior. The casino needs updating with better games, better Sportsbook and better bars."
The price is NZ$323
includes taxes & fees
2 Jun - 3 Jun
Belterra Casino Resort
Best Way Inn Madison
2.5 star property
6.6 out of 10, (412)
"Rooms are a little dated but the area is great people are super friendly."
The price is NZ$144
includes taxes & fees
4 Jun - 5 Jun
Best Way Inn Madison
Ramada by Wyndham Sparta/At Speedway
2.5 star property
7.6 out of 10, Good, (1001)
"Well lighted , no steps !"
The price is NZ$127
includes taxes & fees
2 Jun - 3 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Prestonville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Prestonville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Prestonville. Seeing all the best attractions is bound to make you fall in love with Prestonville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Prestonville short-term rentals, that won’t be hard to do.

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?

Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River: This holiday home rental outside of Prestonville comes with WiFi so that you can feel at home during your trip.

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.

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