A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.

Madison Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Madison vacation rentals

WiFi (free), bed sheets

1. Romantic Woodside Cabin | Hot Tub & Fire Pit

Romantic Woodside Cabin | Hot Tub & Fire Pit
Madison
9.6 out of 10, Exceptional, (5 reviews)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
The price is ￥32,166
￥40,793 total
includes taxes & fees
Sep 7 - Sep 8
Romantic Woodside Cabin | Hot Tub & Fire Pit
Coffee/tea maker, fridge, microwave, oven

2. Dog-Friendly Retreat Near Wineries/Spire/GOTL

Dog-Friendly Retreat Near Wineries/Spire/GOTL
Madison-on-the-Lake
9.6 out of 10, Exceptional, (38 reviews)
"Great stay will be back again "
United States
andrea c.
The price is ￥21,095
￥38,877 total
includes taxes & fees
Sep 8 - Sep 9
Dog-Friendly Retreat Near Wineries/Spire/GOTL
Outdoor spa tub

3. Gorgeous Tent Rental Great for Glamping in Ohio

Gorgeous Tent Rental Great for Glamping in Ohio
Madison
The price is ￥19,423
￥23,520 total
includes taxes & fees
Sep 8 - Sep 9
Gorgeous Tent Rental Great for Glamping in Ohio
Dining

4. Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!

Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
Madison-on-the-Lake
10.0 out of 10, Exceptional, (4 reviews)
"Good location and a cute space. "
United States
Veronica K.
The price is ￥26,158
￥53,913 total
includes taxes & fees
Sep 15 - Sep 16
Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
On the beach

5. LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (19 reviews)
"We really enjoyed our stay in the Lemon Drop Cottage. It was clean with a comfortable bed, wonderfully decorated, in a great location, and had everything we needed plus access to the lake and plenty of room for our dog."
United States
David D.
The price is ￥27,814
￥44,690 total
includes taxes & fees
Sep 7 - Sep 8
LemonDrop Lake-Front Cottage
TV, fireplace, stereo

6. SeaSide Lake-Front Cottage

SeaSide Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (14 reviews)
"The cottage is beautifully cared for and filled with little thoughtful details. The view is great and the location is perfect. We absolutely loved our stay and can't wait to go back!"
United States
Jocelyn S.
The price is ￥31,096
￥48,441 total
includes taxes & fees
Sep 22 - Sep 23
SeaSide Lake-Front Cottage
Coffee/tea maker, fridge, oven, stovetop

7. Ledge House Vintage Retreat | Hot Tub & Fire Pit

Ledge House Vintage Retreat | Hot Tub & Fire Pit
Madison
The price is ￥66,309
￥83,027 total
includes taxes & fees
Sep 17 - Sep 18
Ledge House Vintage Retreat | Hot Tub & Fire Pit
Interior

8. Highland House | Wine Country | Private Hot Tub

Highland House | Wine Country | Private Hot Tub
Madison
The price is ￥46,542
￥58,962 total
includes taxes & fees
Sep 7 - Sep 8
Highland House | Wine Country | Private Hot Tub
Outdoor dining

9. Charming 2-bedroom house in delightful Madison with AC

Charming 2-bedroom house in delightful Madison with AC
Madison-on-the-Lake
8.0 out of 10, Very Good, (5 reviews)
The price is ￥46,878
￥55,472 total
includes taxes & fees
Sep 9 - Sep 10
Charming 2-bedroom house in delightful Madison with AC
Outdoor spa tub

10. Vineyard View-Walkable to Two Wineries + River| Hot Tub, Karaoke, Fireplace

Vineyard View-Walkable to Two Wineries + River| Hot Tub, Karaoke, Fireplace
Madison
10.0 out of 10, Exceptional, (70 reviews)
"Great amenities and beautiful setting"
United States
Joyce L.
The price is ￥76,633
￥110,851 total
includes taxes & fees
Sep 13 - Sep 14
Vineyard View-Walkable to Two Wineries + River| Hot Tub, Karaoke, Fireplace
TV, fireplace, stereo

11. Tree-Top Lake-Front Cottage

Tree-Top Lake-Front Cottage
Madison-on-the-Lake
9.6 out of 10, Exceptional, (19 reviews)
"Top notch hospitality...Dan and Brenda go outta the way to make your stay great!!! The little details they put into their place make it top notch along with the fires at the lakeside!!!!"
United States
Haley K.
The price is ￥31,096
￥48,441 total
includes taxes & fees
Sep 7 - Sep 8
Tree-Top Lake-Front Cottage
Outdoor dining

12. Lakeside Chalet | Private Lake | Hot Tub | Views

Lakeside Chalet | Private Lake | Hot Tub | Views
Madison
The price is ￥53,730
￥67,187 total
includes taxes & fees
Sep 13 - Sep 14
Lakeside Chalet | Private Lake | Hot Tub | Views
Coffee/tea maker, fridge, microwave, oven

13. Chardonnay Cottage - GOTL Strip - Cozy & Quaint

Chardonnay Cottage - GOTL Strip - Cozy & Quaint
Geneva
10.0 out of 10, Exceptional, (21 reviews)
"Clean Room, good quality stay for price"
United States
Dainen
The price is ￥8,438
￥32,708 total
includes taxes & fees
Oct 7 - Oct 8
Chardonnay Cottage - GOTL Strip - Cozy & Quaint
Living area

14. A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (20 reviews)
"Good stay"
Canada
Corey
The price is ￥15,329
￥32,830 total
includes taxes & fees
Sep 9 - Sep 10
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
2 bedrooms, WiFi (free), bed sheets

15. A great stay, close to Spire, GOTL, & Wineries....King Bed!

A great stay, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (46 reviews)
"Cute rental in a great location not far from shopping and the lake !!! Our family had a great stay here we made so many memories. The arcade was a big hit!"
United States
ceberio68
The price is ￥13,923
￥30,018 total
includes taxes & fees
Sep 13 - Sep 14
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Terrace/patio

16. Walk to Lake & Strip | Firepit & Grill

Walk to Lake & Strip | Firepit & Grill
Geneva
8.8 out of 10, Excellent, (115 reviews)
"Inside was cute and cozy. Perfect for my husband and I. Strip was in easy walking distance. Bed was comfortable. I will definitely stay here in number 7. Don’t judge a book by its cover as the outside is definitely an older cottage."
United States
Elaine E.
The price is ￥6,013
￥23,964 total
includes taxes & fees
Sep 9 - Sep 10
Walk to Lake & Strip | Firepit & Grill
Outdoor dining

17. Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay :) "
United States
Jennifer S.
The price is ￥20,314
￥26,393 total
includes taxes & fees
Sep 18 - Sep 19
Beautiful cabin situated on wooded land with nice yard clearing and small stream
Property grounds

18. Charming 1-bedroom cabin in Geneva

Charming 1-bedroom cabin in Geneva
Geneva
9.8 out of 10, Exceptional, (8 reviews)
"Great out of the grid hideaway. Hosts are very nice, thanks for having us! "
United States
nina H.
The price is ￥18,282
￥22,138 total
includes taxes & fees
Sep 14 - Sep 15
Charming 1-bedroom cabin in Geneva
Property grounds

19. Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.6 out of 10, Exceptional, (12 reviews)
"Very nice property"
United States
William M B.
The price is ￥18,704
￥23,861 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Shed-Teau in Geneva + Firepit
Coffee/tea maker, fridge, microwave, oven

20. Recently updated apartment in a Triplex unit #1 close to wineries and the lake.

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
Geneva
9.6 out of 10, Exceptional, (42 reviews)
"Very nice place. Nice location. Would stay there again."
United States
Kelly B.
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
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 Madison Hotel Reviews

Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

10/10 Excellent
"I stayed here two months ago and also chose to stay here on my next visit. This motel is the best in the area . Everything was awesome and very clean and the staff made sure my visit was great. Definitely a great place to stay 🙂"
deborah 2-night trip
Posted less than an hour ago
Wingate by Wyndham Geneva at SPIRE Academy

Find out more about Madison

Search for holiday rentals in Madison on Expedia! You can easily find your home rentals, villas, holiday apartments in Madison using one of the methods below:

  • View our selection of featured holiday rentals in Madison
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  • Enter your travel dates to view the best deals on holiday rentals in Madison while they last

Look no further and take a look at our great range of rental properties in Madison!

Frequently asked questions

Can I find a vacation rental in Madison?

Yes, you can find vacation rentals in Madison close to Rabbit Run Community Arts Association, or you can go with a secluded option if you want a relaxing stay. Madison is known for its wineries and theaters. Make sure you have time to check out the restaurants while you're in the area.

What's the top vacation rental in Madison?

Perfect Blissful 3 Bedroom Retreat Near Lake Erie, Spire, Wine Country, & Trails: Visitors give good reviews to this Madison vacation home rental, which is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. Some other top choices in Madison are Hot Tub Escape Near Wineries+ Lake and Lakefront Retreat w/ Private Beach. Sleeps 12.

How many vacation rentals will I find in Madison?

With 36 Expedia vacation rentals, you're sure to find just the right place for your Madison stay.

What can I see and do in Madison?

Lake Erie and Hogback Ridge are a couple of scenic spots to enjoy the outdoors, whereas Rabbit Run Community Arts Association is one of the cultural attractions. While here, Laurentia Vineyard & Winery and Chalet Debonne Vineyards are other places worth a visit.

What are vacation rentals like in Madison?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Madison. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.