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Prestonville Vacation Rentals

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Check prices for these dates

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

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
10.0 out of 10, Exceptional, (17 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is ￥14,064
￥26,323 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥13,274
￥22,578 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥20,701
￥37,830 total
includes taxes & fees
Oct 21 - Oct 22
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 ￥14,080
￥27,096 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is ￥15,802
￥28,444 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥14,791
￥27,913 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥21,649
￥40,975 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥20,622
￥38,436 total
includes taxes & fees
Oct 22 - Oct 23
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 ￥16,355
￥34,801 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥19,768
￥41,270 total
includes taxes & fees
Oct 21 - Oct 22
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 ￥26,310
￥34,437 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥20,622
￥40,435 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥17,382
￥29,154 total
includes taxes & fees
Oct 21 - Oct 22
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 ￥15,802
￥28,444 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥15,802
￥28,444 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥20,622
￥42,615 total
includes taxes & fees
Oct 22 - Oct 23
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 ￥17,777
￥34,424 total
includes taxes & fees
Oct 31 - Nov 1
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 ￥24,335
￥44,427 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥15,217
￥28,548 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥23,442
￥47,279 total
includes taxes & fees
Oct 19 - Oct 20
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 10 hours ago
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Find out more about Prestonville

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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.