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Prestonville Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Prestonville holiday rentals

A wooden cabin with a porch, a staircase, and a deck.

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 AU$243
includes taxes & fees
9 Nov - 10 Nov
Sassafras Woodland Cabin at Lost Trails
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

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 AU$210
includes taxes & fees
17 Nov - 18 Nov
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
A cozy wooden cabin interior with a sofa, a dining table, and a TV.

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 AU$347
includes taxes & fees
18 Oct - 19 Oct
Cabin on the Ridge: The Sequel
Property grounds

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 AU$250
includes taxes & fees
19 Oct - 20 Oct
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
cd294e93-b148-4eb4-b858-151fabf1d0ec

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 AU$262
includes taxes & fees
16 Nov - 17 Nov
Maple Cozy Cabin at Lost Trails
A cozy room with a bed, a chair, a sofa, and a small table.

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 AU$257
includes taxes & fees
15 Nov - 16 Nov
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A covered porch with a wooden door, potted plants, and a metal railing.

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 AU$374
includes taxes & fees
25 Oct - 26 Oct
The Artist’s A-Frame
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

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 AU$347
includes taxes & fees
22 Oct - 23 Oct
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

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 AU$322
includes taxes & fees
29 Oct - 30 Oct
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A log cabin with a covered porch, wooden rocking chairs, and a potted plant.

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 AU$374
includes taxes & fees
21 Oct - 22 Oct
Stoney Creek - Sit back and unwind
An outdoor patio with wicker furniture, a fire pit, and a table with candles and fruit.

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 AU$312
includes taxes & fees
22 Oct - 23 Oct
Romantic 1 BR Retreat on the edge of woods with private hot tub
A residential property with a red door, a small front yard with grass and shrubs, and a neighboring church with a steeple.

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 AU$370
includes taxes & fees
18 Oct - 19 Oct
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

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 AU$268
includes taxes & fees
17 Nov - 18 Nov
Cedar Rustic Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

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 AU$263
includes taxes & fees
9 Nov - 10 Nov
Mulberry Secluded Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

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 AU$270
includes taxes & fees
22 Oct - 23 Oct
Walnut Secluded Cabin at Lost Trails
A living room with a brown leather sofa, a cowhide rug, and a cowhide-patterned armchair.

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 price is AU$385
includes taxes & fees
22 Oct - 23 Oct
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A bedroom with a bed, a decorative wall piece, a rug, and a window with curtains.

17. The River View at Esther’s

The River View at Esther’s
Vevay
The price is AU$319
includes taxes & fees
18 Oct - 19 Oct
The River View at Esther’s
A spacious wooden cabin with a loft bedroom, a dining area, and a kitchen.

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 AU$407
includes taxes & fees
29 Oct - 30 Oct
Cabin on the Ridge
A modern kitchen with a wooden countertop, black stools, and a wall-mounted TV.

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 AU$273
includes taxes & fees
26 Oct - 27 Oct
The Blue Door Place
A hallway with a wooden floor, a brick wall, and a door with a window.

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.
The price is AU$432
includes taxes & fees
18 Oct - 19 Oct
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

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

8/10 Good
"Beautiful hotel and setting, very clean and scenic. However poor mattress quality did not allow a good night's sleep."
Andrew 2-night trip
Posted 3 hours ago
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Find out more about Prestonville

Everything you need to know about Prestonville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Prestonville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Prestonville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Prestonville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Prestonville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Prestonville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Prestonville holiday rentals we have selected for you start as low as AU$210 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Prestonville rentals

At Expedia, we put the best Prestonville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Prestonville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Prestonville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Prestonville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.