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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Madison vacation rentals

1. Gorgeous Tent Rental Great for Glamping in Ohio

Gorgeous Tent Rental Great for Glamping in Ohio
Madison
$149 nightly
The price is $155
Oct 4 - Oct 5
Total with taxes and fees
Gorgeous Tent Rental Great for Glamping in Ohio
A bedroom with a wooden ceiling, a bed with a wooden headboard, a blue chair, a bench, and a cowhide rug.

2. 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
$245 nightly
The price is $272
Oct 6 - Oct 7
Total with taxes and fees
Romantic Woodside Cabin | Hot Tub & Fire Pit
A beach with a chair and a rock formation in the background.

3. LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (21 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.
$312 nightly
The price is $312
Oct 12 - Oct 13
Total with taxes and fees
LemonDrop Lake-Front Cottage
A living room with a leather couch, a fireplace, and a large window offering a view of the ocean.

4. SeaSide Lake-Front Cottage

SeaSide Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (16 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.
$273 nightly
The price is $273
Nov 1 - Nov 2
Total with taxes and fees
SeaSide Lake-Front Cottage
A dining area with a white table and black chairs, large windows with a view of a green landscape, and a small potted plant on the table.

5. 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, (5 reviews)
"Good location and a cute space. "
United States
Veronica K.
$330 nightly
The price is $344
Oct 6 - Oct 7
Total with taxes and fees
Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
A modern kitchen with blue cabinets, a stainless steel dishwasher, a gas stove, and a microwave.

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

Dog-Friendly Retreat Near Wineries/Spire/GOTL
Madison-on-the-Lake
9.6 out of 10, Exceptional, (39 reviews)
"Great stay will be back again "
United States
andrea c.
$302 nightly
The price is $317
Oct 4 - Oct 5
Total with taxes and fees
Dog-Friendly Retreat Near Wineries/Spire/GOTL
A foosball table with a wooden frame and black handles.

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

Ledge House Vintage Retreat | Hot Tub & Fire Pit
Madison
$392 nightly
The price is $436
Oct 6 - Oct 7
Total with taxes and fees
Ledge House Vintage Retreat | Hot Tub & Fire Pit
A large two-story house with a covered porch and a small shed.

8. Highland House | Wine Country | Private Hot Tub

Highland House | Wine Country | Private Hot Tub
Madison
$407 nightly
The price is $454
Oct 6 - Oct 7
Total with taxes and fees
Highland House | Wine Country | Private Hot Tub
A backyard patio with a table and chairs, a grill, and a barbecue smoker.

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)
$355 nightly
The price is $355
Oct 4 - Oct 5
Total with taxes and fees
Charming 2-bedroom house in delightful Madison with AC
A living room with a leather sofa, a dining table with chairs, a TV, a fireplace, and large windows overlooking the ocean.

10. Tree-Top Lake-Front Cottage

Tree-Top Lake-Front Cottage
Madison-on-the-Lake
9.6 out of 10, Exceptional, (20 reviews)
"Excellent cottage,location,& Host"
United States
Kelly Lee F.
$273 nightly
The price is $273
Nov 1 - Nov 2
Total with taxes and fees
Tree-Top Lake-Front Cottage
A lakeside dock with a wooden pier extending into the water, surrounded by lush greenery and trees.

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

Lakeside Chalet | Private Lake | Hot Tub | Views
Madison
$494 nightly
The price is $550
Oct 5 - Oct 6
Total with taxes and fees
Lakeside Chalet | Private Lake | Hot Tub | Views
A stone fire pit with burning logs, surrounded by a grassy area and two wooden chairs.

12. Center Strip | Pets OK | Wi-Fi | Near Wineries

Center Strip | Pets OK | Wi-Fi | Near Wineries
Geneva
9.4 out of 10, Exceptional, (258 reviews)
"Very enjoyable stay. Very clean and well kept . Very convenient location. We highly recommend !"
United States
Kevin A.
$158 nightly
The price is $169
Oct 4 - Oct 5
Total with taxes and fees
Center Strip | Pets OK | Wi-Fi | Near Wineries
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

13. 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
$199 nightly
The price is $199
Oct 4 - Oct 5
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
A compact living space with a kitchenette, a dining area with bar stools, a television, and a ceiling fan.

14. The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
10.0 out of 10, Exceptional, (26 reviews)
"Loved it!! I’ll definitely stay here again! "
United States
Rebecca S.
$204 nightly
The price is $208
Oct 25 - Oct 26
Total with taxes and fees
The Riesling Cottage - GOTL Strip - Cozy & Quaint
A living room with a brown sofa, a coffee table, a TV, and a ceiling fan.

15. 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, (22 reviews)
"Good stay"
Canada
Corey
$206 nightly
The price is $206
Oct 5 - Oct 6
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A small house with solar panels, a porch with outdoor furniture, and a wooden deck.

16. Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.6 out of 10, Exceptional, (14 reviews)
"Very nice property"
United States
William M B.
$143 nightly
The price is $143
Oct 6 - Oct 7
Total with taxes and fees
Cozy Shed-Teau in Geneva + Firepit
A backyard with a stone fire pit, outdoor seating, and a covered pavilion.

17. Charming 1-bedroom cabin in Geneva

Charming 1-bedroom cabin in Geneva
Geneva
9.0 out of 10, Wonderful, (10 reviews)
"They are scammers; they claimed it was a private cabin, but when I arrived, I found a family living inside. I didn't even stay—I lost the money—and when I asked for a refund, they wouldn't give it back."
United States
Wideleine
$171 nightly
The price is $176
Oct 9 - Oct 10
Total with taxes and fees
Charming 1-bedroom cabin in Geneva
A circular arrangement of wooden Adirondack chairs around a central fire pit in a gravel area with a wooden fence and buildings in the background.

18. Pet Friendly | Walk to Lake | Firepit & Grill

Pet Friendly | Walk to Lake | Firepit & Grill
Geneva
9.6 out of 10, Exceptional, (231 reviews)
"Location was great. Property was very clean. Fire pit area was smaller than expected and we didn’t realize we had to share with the other guests. But would stay there again."
United States
Melina
Pet Friendly | Walk to Lake | Firepit & Grill
A compact living space with a kitchenette, a dining area, and a sofa with cushions.

19. Little oasis a short walk from GOTL strip

Little oasis a short walk from GOTL strip
Geneva-on-the-Lake
10.0 out of 10, Exceptional, (113 reviews)
"It was an adorable and super clean cottage! Felt very at home and cozy. Definitely would rent again."
United States
Rachel
$216 nightly
The price is $216
Oct 6 - Oct 7
Total with taxes and fees
Little oasis a short walk from GOTL strip
A sunset over a calm sea with a clear horizon.

20. "The Beach Hive" unit 1; lower-level apartment on the Lake

"The Beach Hive" unit 1; lower-level apartment on the Lake
Geneva
9.4 out of 10, Exceptional, (122 reviews)
"Great location!"
United States
Nicholas
$160 nightly
The price is $167
Oct 26 - Oct 27
Total with taxes and fees
"The Beach Hive" unit 1; lower-level apartment on 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
"The hotel was clean and the breakfast was good the staff was very nice"
Tammy 1-night trip
Posted 8 hours ago
Wingate by Wyndham Geneva at SPIRE Academy

Find out more about Madison

Everything you need to know about Madison 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 Madison 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 Madison vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. 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 Madison 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 $148 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 Madison rentals

At Expedia, we put the best Madison 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 Madison 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 Madison 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 Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Charming 2-bedroom house in delightful Madison with AC: Visitors give good reviews to this Madison vacation home rental, which is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation with a garden and a selection of books. Some other top choices in Madison are Lakefront Retreat w/ Private Beach. Sleeps 12 and Lake Erie Beachfront Retreat - 8 BR + Private Beach & Hot tub!.

How many vacation rentals will I find in Madison?

With 38 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 Grand River Cellars Winery 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.