Prestonville Vacation Rentals

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Oct 26 - Oct 27
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Oct 27 - Oct 28
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Oct 31 - Nov 2
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Nov 7 - Nov 9

Vacation Rentals in Prestonville

Fridge, microwave, oven, stovetop
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!
9.8 out of 10, Exceptional, (44)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is ￥16,050
￥34,279 total
includes taxes & fees
Oct 30 - Oct 31
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Interior
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
10.0 out of 10, Exceptional, (54)
"Great property, great location, and amazing hosts. Incredible attention to detail and service. It would take too long to describe everything that impressed us so I'll just say it's all perfect and if this place is available when you're visiting Madison, stop searching and just book it."
United States
John S.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Interior
Sunset over the city Suite 201, Sunset over the city Suite 201
Sunset over the city Suite 201, Sunset over the city Suite 201
9.6 out of 10, Exceptional, (10)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
United States
Sarah D.
The price is ￥11,159
￥20,042 total
includes taxes & fees
Nov 3 - Nov 4
Sunset over the city Suite 201, Sunset over the city Suite 201
4 bedrooms, free WiFi, bed sheets
Rustic cabin just outside of Madison!
Rustic cabin just outside of Madison!
10.0 out of 10, Exceptional, (49)
"Great day, we loved the cabin!"
United States
Mark C.
Rustic cabin just outside of Madison!
Interior
Stoney Creek - Sit back and unwind
Stoney Creek - Sit back and unwind
10.0 out of 10, Exceptional, (99)
"Stayed with my Wife for a week after our wedding and it the perfect place to recharge after the rollercoaster of emotions that we had dealt with during the wedding. Would definitely recommend to anyone who is looking for a relaxing and comfortable place to stay. "
United States
Joshua C.
Stoney Creek - Sit back and unwind
Fridge, microwave, oven, stovetop
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
9.8 out of 10, Exceptional, (57)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
The price is ￥12,993
￥35,219 total
includes taxes & fees
Oct 28 - Oct 29
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Outdoor spa tub
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Peaceful getaway centrally located just min. from Madison and Belterra casino.
9.4 out of 10, Exceptional, (29)
"Very nice place!"
United States
Lynn C.
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Property grounds
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
9.8 out of 10, Exceptional, (8)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
The price is ￥9,172
￥17,274 total
includes taxes & fees
Nov 24 - Nov 25
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
TV, fireplace
Cozy Cabin Madison Indiana
Cozy Cabin Madison Indiana
10.0 out of 10, Exceptional, (17)
"The cabin was just as described online it's very quiet and was the perfect getaway "
United States
christy m.
Cozy Cabin Madison Indiana
Fridge, microwave, oven, stovetop
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
9.6 out of 10, Exceptional, (19)
"Perfect little cozy cabin for an amazing getaway! We were able to just relax and enjoy our time together with zero distractions. 10/10 would definitely stay here again! "
United States
ryan w.
The price is ￥27,515
￥44,299 total
includes taxes & fees
Oct 28 - Oct 29
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Property grounds
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
10.0 out of 10, Exceptional, (208)
"This place checks all of our boxes for the things we look for in a rental cabin. "
United States
Brian and Holly w.
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Dining
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
9.6 out of 10, Exceptional, (21)
"Very nice house good accommodations would stay again !!!"
United States
Henry C.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
10.0 out of 10, Exceptional, (15)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is ￥17,747
￥34,473 total
includes taxes & fees
Oct 30 - Oct 31
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Exterior
Rustic Cabin at Lost Trails
Rustic Cabin at Lost Trails
10.0 out of 10, Exceptional, (16)
"This cabin was peaceful and the perfect getaway for anyone. Would definitely recommend booking and staying here. "
United States
Lema W.
Rustic Cabin at Lost Trails
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
2.0 star property
10.0 out of 10, Exceptional, (12)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
United States
1969matty
The price is ￥19,260
￥25,665 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Dining
Madison's Only YURT Experience
Madison's Only YURT Experience
9.2 out of 10, Wonderful, (11)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
United States
Nicole E.
Madison's Only YURT Experience
2 bedrooms, free WiFi, bed sheets
Unique Secluded Cabin with Loft on Classified Forest
Unique Secluded Cabin with Loft on Classified Forest
9.6 out of 10, Exceptional, (44)
"beautiful cabin. picture perfect very secluded "
United States
Deborah P.
Unique Secluded Cabin with Loft on Classified Forest
Fridge, microwave, oven, stovetop
The Wadsworth in National Historic District of Madison, Indiana.
The Wadsworth in National Historic District of Madison, Indiana.
10.0 out of 10, Exceptional, (61)
"Decorating was very nice. Loved the back patio. The whole experience was just perfect. I highly recommend this property. "
United States
Patricia H.
The Wadsworth in National Historic District of Madison, Indiana.
Microwave, oven, stovetop, dishwasher
Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront
Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront
10.0 out of 10, Exceptional, (1)
"Our stay at this beautiful old home on Main Street in Madison was fantastic. The property has been beautifully maintained and modernized just enough to be comfortable without losing the gorgeous, authentic feel of an old home that clearly has stories to tell.The rooms were spacious and incredibly comfortable, providing plenty of room to relax. The location simply can't be beat—we loved that we could easily walk to all the local shops and great restaurants.Finally, the hosts were wonderfully...
United States
Lee M.
The price is ￥48,151
￥92,641 total
includes taxes & fees
Oct 28 - Oct 29
Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront
Exterior
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
10.0 out of 10, Exceptional, (1)
"Cozy, fun get away close to downtown yet secluded enough to feel like you had privacy. "
United States
Raena E.
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
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

Quality Inn

Quality Inn

10/10 Excellent
"Good price."
Lee 1-night trip
Posted 2 days ago
Quality Inn

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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: Visitors like this Prestonville vacation home rental. It offers a patio, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Lanier Mansion.

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.