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Prestonville Holiday Rentals

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Our top choices for Prestonville holiday rentals

1. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (17 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is NZ$295
includes taxes & fees
9 Nov - 10 Nov
Sassafras Woodland Cabin at Lost Trails

2. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison Historic District
9.6 out of 10, Exceptional, (23 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
The price is NZ$255
includes taxes & fees
17 Nov - 18 Nov
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

3. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful, clean, serene! Perfect place for a weekend anniversary getaway!"
United States
Mallory T.
The price is NZ$413
includes taxes & fees
18 Oct - 19 Oct
Cabin on the Ridge: The Sequel

4. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is NZ$313
includes taxes & fees
15 Nov - 16 Nov
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

5. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is NZ$318
includes taxes & fees
16 Nov - 17 Nov
Maple Cozy Cabin at Lost Trails

6. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison Historic District
9.6 out of 10, Exceptional, (8 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is NZ$313
includes taxes & fees
9 Nov - 10 Nov
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

7. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (41 reviews)
"Very cool house in a nice neighborhood. Had everything we needed and was close to anything you want to do in Madison. We will definitely stay there again!"
United States
Dean C.
The price is NZ$442
includes taxes & fees
16 Nov - 17 Nov
The Artist’s A-Frame

8. The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (51 reviews)
"Had a very nice stay"
United States
Brad P.
The price is NZ$431
includes taxes & fees
25 Oct - 26 Oct
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

9. Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (78 reviews)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
The price is NZ$402
includes taxes & fees
15 Nov - 16 Nov
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

10. Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind
Madison
10.0 out of 10, Exceptional, (130 reviews)
"Our family enjoyed our stay."
United States
Shanna S.
The price is NZ$460
includes taxes & fees
21 Oct - 22 Oct
Stoney Creek - Sit back and unwind

11. Romantic 1 BR Retreat on the edge of woods with private hot tub

Romantic 1 BR Retreat on the edge of woods with private hot tub
Madison
10.0 out of 10, Exceptional, (1 review)
"This was a relaxing & romantic way to celebrate our 57th wedding anniversary. Everything was clean & the host very cordial. We enjoyed the rear deck with its fireplace & hot tube as as the comfortable bed & romantic tent interior."
United States
jon h.
The price is NZ$379
includes taxes & fees
22 Oct - 23 Oct
Romantic 1 BR Retreat on the edge of woods with private hot tub

12. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison Historic District
9.0 out of 10, Wonderful, (2 reviews)
"Good location, well stocked with essentials."
United States
Leslie W.
The price is NZ$443
includes taxes & fees
18 Oct - 19 Oct
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

13. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is NZ$328
includes taxes & fees
21 Oct - 22 Oct
Cedar Rustic Cabin at Lost Trails

14. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"This is a total hidden gem! The cabin seemed brand new and was outfitted with everything you might need. We spent our 25th wedding anniversary weekend here and loved every second! Would highly recommend!"
United States
Jodi E.
The price is NZ$318
includes taxes & fees
9 Nov - 10 Nov
Mulberry Secluded Cabin at Lost Trails

15. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is NZ$318
includes taxes & fees
20 Oct - 21 Oct
Walnut Secluded Cabin at Lost Trails

16. 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, (54 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

17. The River View at Esther’s

The River View at Esther’s
Vevay
The price is NZ$381
includes taxes & fees
18 Oct - 19 Oct
The River View at Esther’s

18. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (21 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is NZ$485
includes taxes & fees
28 Oct - 29 Oct
Cabin on the Ridge

19. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (30 reviews)
"Very clean, had everything we needed! "
United States
james w.
The price is NZ$323
includes taxes & fees
19 Oct - 20 Oct
The Blue Door Place

20. 604 GQ on Mulberry: 2 King Luxury Suites, Patio

604 GQ on Mulberry: 2 King Luxury Suites, Patio
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"Great property and a lot of room which was great."
United States
Kathryn B.
604 GQ on Mulberry: 2 King Luxury Suites, Patio
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 Prestonville Hotel Reviews

Find out more about Prestonville

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?

Red comfy cottage : This holiday home rental outside of Prestonville offers an indoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Schofield House.

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.