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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Madison vacation rentals

A bedroom with a wooden ceiling, a bed with a wooden headboard, a blue chair, a bench, and a cowhide rug.

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
$221 nightly
The price is $245
Oct 21 - Oct 22
Total with taxes and fees
Romantic Woodside Cabin | Hot Tub & Fire Pit
A living room with a leather couch, a fireplace, and a large window offering a view of the ocean.

2. 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.
$275 nightly
The price is $275
Nov 2 - Nov 3
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.

3. 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.
$299 nightly
The price is $306
Oct 12 - Oct 13
Total with taxes and fees
Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
A foosball table with a wooden frame and black handles.

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

Ledge House Vintage Retreat | Hot Tub & Fire Pit
Madison
$331 nightly
The price is $367
Oct 20 - Oct 21
Total with taxes and fees
Ledge House Vintage Retreat | Hot Tub & Fire Pit
A modern kitchen with blue cabinets, a stainless steel dishwasher, a gas stove, and a microwave.

5. 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.
$305 nightly
The price is $320
Oct 14 - Oct 15
Total with taxes and fees
Dog-Friendly Retreat Near Wineries/Spire/GOTL
A large two-story house with a covered porch and a small shed.

6. Highland House | Wine Country | Private Hot Tub

Highland House | Wine Country | Private Hot Tub
Madison
$323 nightly
The price is $359
Oct 20 - Oct 21
Total with taxes and fees
Highland House | Wine Country | Private Hot Tub
A large, multi-story house with a stone facade, a spacious driveway, and a well-maintained lawn.

7. 3-bedroom pet friendly home in Madison walking distance to beach & winery

3-bedroom pet friendly home in Madison walking distance to beach & winery
Madison-on-the-Lake
10.0 out of 10, Exceptional, (2 reviews)
"The host was responsive and kind. The house was very well equipped, clean and comfortable! 5 stars!"
United States
Stacy S.
$264 nightly
The price is $264
Nov 1 - Nov 2
Total with taxes and fees
3-bedroom pet friendly home in Madison walking distance to beach & winery
A beach with a chair and a rock formation in the background.

8. LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (22 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.
$264 nightly
The price is $264
Nov 5 - Nov 6
Total with taxes and fees
LemonDrop Lake-Front Cottage
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)
"The host was very accommodating and very helpful. This house was just what I needed."
United States
Toni L.
$355 nightly
The price is $355
Oct 11 - Oct 12
Total with taxes and fees
Charming 2-bedroom house in delightful Madison with AC
Property grounds

10. Gorgeous Tent Rental Great for Glamping in Ohio

Gorgeous Tent Rental Great for Glamping in Ohio
Madison
$149 nightly
The price is $155
Oct 11 - Oct 12
Total with taxes and fees
Gorgeous Tent Rental Great for Glamping in Ohio
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
$409 nightly
The price is $456
Oct 18 - Oct 19
Total with taxes and fees
Lakeside Chalet | Private Lake | Hot Tub | Views
A living room with a leather sofa, a dining table with chairs, a TV, a fireplace, and large windows overlooking the ocean.

12. 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.
$274 nightly
The price is $274
Nov 1 - Nov 2
Total with taxes and fees
Tree-Top Lake-Front Cottage
A living room with a brown sofa, a coffee table, a TV, and a ceiling fan.

13. 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, (23 reviews)
"Good stay"
Canada
Corey
$205 nightly
The price is $205
Oct 12 - Oct 13
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

14. 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 18 - Oct 19
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
A single-story house with a porch, a door, and a window.

15. Adorable and Cozy GOTL Cottage - Pet Friendly

Adorable and Cozy GOTL Cottage - Pet Friendly
Geneva
10.0 out of 10, Exceptional, (3 reviews)
"Everything was top rate right down to the plush bathroom towels and as others have mentioned the shower was doable. We were in the area to visit family, so we only needed a place to sleep and clean up. Would differently use again."
United States
George
$275 nightly
The price is $310
Oct 11 - Oct 12
Total with taxes and fees
Adorable and Cozy GOTL Cottage - Pet Friendly
A small cabin with a porch, two Adirondack chairs, a round table, and a screened-in area.

16. Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.4 out of 10, Exceptional, (18 reviews)
"Host was amazing"
United States
Kim C.
$160 nightly
The price is $170
Oct 11 - Oct 12
Total with taxes and fees
Cabin 1 The Sunrise Patio
A compact living space with a kitchenette, a dining area with bar stools, a television, and a ceiling fan.

17. 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 12 - Oct 13
Total with taxes and fees
The Riesling Cottage - GOTL Strip - Cozy & Quaint
A beach at sunset with waves crashing onto the shore.

18. LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until Oct. 30- ask!

LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until Oct. 30- ask!
Geneva
10.0 out of 10, Exceptional, (400 reviews)
"Great place to stay! Convenient location!"
United States
Debbie C.
$140 nightly
The price is $148
Oct 26 - Oct 27
Total with taxes and fees
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until Oct. 30- ask!
A square fire pit table with two metal chairs on a wooden deck.

19. 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
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful stay :) "
United States
Jennifer S.
$165 nightly
The price is $169
Oct 30 - Oct 31
Total with taxes and fees
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A small house with solar panels, a porch with outdoor furniture, and a wooden deck.

20. 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.
$136 nightly
The price is $136
Oct 13 - Oct 14
Total with taxes and fees
Cozy Shed-Teau in Geneva + Firepit
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

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 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.