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Prestonville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Prestonville vacation 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
9.8 out of 10, Exceptional, (18 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
$142 nightly
The price is $164
Nov 9 - Nov 10
Total with taxes and fees
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
$134 nightly
The price is $143
Nov 18 - Nov 19
Total with taxes and fees
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.
$210 nightly
The price is $237
Oct 21 - Oct 22
Total with taxes and fees
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, (18 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.
$149 nightly
The price is $171
Nov 2 - Nov 3
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
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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.
$155 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
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.
$154 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
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.
$230 nightly
The price is $259
Oct 25 - Oct 26
Total with taxes and fees
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.
$211 nightly
The price is $242
Oct 22 - Oct 23
Total with taxes and fees
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.
$191 nightly
The price is $219
Oct 20 - Oct 21
Total with taxes and fees
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.
$226 nightly
The price is $260
Oct 21 - Oct 22
Total with taxes and fees
Stoney Creek - Sit back and unwind
A cozy, illuminated tent-like structure with a green door, surrounded by trees and a gravel path.

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.
$244 nightly
The price is $281
Oct 22 - Oct 23
Total with taxes and fees
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.
$223 nightly
The price is $256
Oct 20 - Oct 21
Total with taxes and fees
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.
$155 nightly
The price is $173
Oct 21 - Oct 22
Total with taxes and fees
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.
$160 nightly
The price is $186
Oct 22 - Oct 23
Total with taxes and fees
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.
$155 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
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.
$228 nightly
The price is $262
Oct 22 - Oct 23
Total with taxes and fees
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
10.0 out of 10, Exceptional, (1 review)
$195 nightly
The price is $218
Oct 31 - Nov 1
Total with taxes and fees
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, (22 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
$249 nightly
The price is $281
Oct 28 - Oct 29
Total with taxes and fees
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.
$161 nightly
The price is $181
Oct 20 - Oct 21
Total with taxes and fees
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.
$268 nightly
The price is $298
Oct 21 - Oct 22
Total with taxes and fees
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

Hillside Inn

Hillside Inn

10/10 Excellent
"Very helpful at check in, great room with a balcony and view, nice breakfast, centrally located."
Kelly 1-night trip
Posted 1 day ago
Hillside Inn

Find out more about Prestonville

Everything you need to know about Prestonville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Prestonville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Prestonville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Prestonville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Prestonville rentals

At Expedia, we put the best Prestonville vacation 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 vacation.

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 vacation rentals in Prestonville?

Yes, you can find vacation rentals close to top points of interest in Prestonville, or you can choose a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Prestonville?

Red comfy cottage : Visitors like this Prestonville vacation home rental. It offers an indoor pool, a patio, and a barbecue grill 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 a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Historic District and Schofield House.

What’s a vacation rental in Prestonville like?

Vacation rentals are privately owned properties you can book for a long or short time in Prestonville. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.