Madison Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Madison vacation rentals

A bedroom with a large bed, a wooden ceiling, and a view of a balcony with outdoor furniture.

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
$147 nightly
The price is $164
Nov 11 - Nov 12
Total with taxes and fees
Romantic Woodside Cabin | Hot Tub & Fire Pit
A house with a white door, grey steps, and two potted yellow flowers at the entrance.

2. The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck

The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck
Madison
$248 nightly
The price is $248
Dec 9 - Dec 10
Total with taxes and fees
The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck
A stone patio with four Adirondack chairs in yellow, green, red, and blue, overlooking a body of water with an American flag on a flagpole.

3. LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (23 reviews)
"Nice stay"
United States
Michael M.
$243 nightly
The price is $243
Nov 15 - Nov 16
Total with taxes and fees
LemonDrop Lake-Front Cottage
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

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, (5 reviews)
"Good location and a cute space. "
United States
Veronica K.
$273 nightly
The price is $280
Nov 17 - Nov 18
Total with taxes and fees
Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
A living room with a leather couch, a fireplace, and a large window offering a view of the ocean.

5. SeaSide Lake-Front Cottage

SeaSide Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (18 reviews)
"The property was gorgeous! We had such a wonderful relaxing time! The unit has everything you could ever need. Thanks!"
United States
Mary G.
$254 nightly
The price is $254
Nov 11 - Nov 12
Total with taxes and fees
SeaSide Lake-Front Cottage
A large, multi-story house with a stone facade, a spacious driveway, and a well-maintained lawn.

6. 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.
$236 nightly
The price is $236
Nov 15 - Nov 16
Total with taxes and fees
3-bedroom pet friendly home in Madison walking distance to beach & winery
A modern living room with a wooden wall, a sofa, a coffee table, and a dining area with chairs.

7. Highland House | Wine Country | Private Hot Tub

Highland House | Wine Country | Private Hot Tub
Madison
$206 nightly
The price is $230
Nov 11 - Nov 12
Total with taxes and fees
Highland House | Wine Country | Private Hot Tub
A modern living room with a sofa, chairs, and a coffee table. Large windows offer a view of trees.

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

Ledge House Vintage Retreat | Hot Tub & Fire Pit
Madison
$225 nightly
The price is $252
Nov 12 - Nov 13
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.

9. 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)
"Amazing stay clean and safe ."
United States
TerriAnn M.
$281 nightly
The price is $296
Nov 11 - Nov 12
Total with taxes and fees
Dog-Friendly Retreat Near Wineries/Spire/GOTL
A modern dining area with a glass table, chairs, and a potted plant.

10. Hot Tub & Fire Table | Madison, Lake Erie

Hot Tub & Fire Table | Madison, Lake Erie
Madison-on-the-Lake
8.8 out of 10, Excellent, (24 reviews)
"We had a wonderful stay here. My grandkids enjoyed the hot tub. I liked the layout of the house and it was very spacious. We were close to the lake, wineries and restaurants.We would definatly come back again."
United States
Kim K.
$413 nightly
The price is $433
Nov 15 - Nov 16
Total with taxes and fees
Hot Tub & Fire Table | Madison, Lake Erie
A backyard patio with a table and chairs, a grill, and a barbecue smoker.

11. 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)
"Beautiful, pet friendly , host was easy to communicate with , we would stay again"
United States
Robin T.
$296 nightly
The price is $296
Nov 11 - Nov 12
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.

12. Tree-Top Lake-Front Cottage

Tree-Top Lake-Front Cottage
Madison-on-the-Lake
9.6 out of 10, Exceptional, (20 reviews)
"What an amazing little cottage with wonderful lake views! The cottage was clean and communication with the owner was fantastic! We loved our time here!"
United States
Andrea T.
$254 nightly
The price is $254
Nov 11 - Nov 12
Total with taxes and fees
Tree-Top Lake-Front Cottage
A cozy living room with a leather sofa, a wooden coffee table, and a large window offering a view of the outdoors.

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

Lakeside Chalet | Private Lake | Hot Tub | Views
Madison
$274 nightly
The price is $307
Nov 12 - Nov 13
Total with taxes and fees
Lakeside Chalet | Private Lake | Hot Tub | Views
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, (49 reviews)
"Very clean.. spacious, Close to wineries."
United States
frances f.
$179 nightly
The price is $179
Nov 22 - Nov 23
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
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, (24 reviews)
"The accommodations were exactly what we were looking for…everything we needed in a comfortable and cozy spot."
United States
Daniel K.
$187 nightly
The price is $187
Nov 16 - Nov 17
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A modern kitchen with dark cabinets, a white stove, and a granite countertop.

16. Chardonnay Cottage - GOTL Strip - Cozy & Quaint

Chardonnay Cottage - GOTL Strip - Cozy & Quaint
Geneva
9.8 out of 10, Exceptional, (25 reviews)
"This cottage was very clean & cozy! We would definitely rent this again. Very close to the strip. Would highly recommend staying here!"
United States
James
$189 nightly
The price is $193
Nov 11 - Nov 12
Total with taxes and fees
Chardonnay Cottage - GOTL Strip - Cozy & Quaint
A small house with solar panels, a porch with outdoor furniture, and a wooden deck.

17. Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.6 out of 10, Exceptional, (15 reviews)
"Very nice property"
United States
William M B.
$128 nightly
The price is $128
Nov 16 - Nov 17
Total with taxes and fees
Cozy Shed-Teau in Geneva + Firepit
A covered outdoor deck with a black wicker sofa, a small table, and a chair.

18. On The Strip • Cozy GOTL Vacation Cottage

On The Strip • Cozy GOTL Vacation Cottage
Geneva
9.4 out of 10, Exceptional, (112 reviews)
"Very pleasant stay"
United States
Daniel M.
$233 nightly
The price is $250
Nov 12 - Nov 13
Total with taxes and fees
On The Strip • Cozy GOTL Vacation Cottage
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.
$151 nightly
The price is $155
Nov 13 - Nov 14
Total with taxes and fees
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden countertop.

20. Recently updated apartment in a Triplex close to Spire Wineries and the Lake.

Recently updated apartment in a Triplex close to Spire Wineries and the Lake.
Geneva
9.4 out of 10, Exceptional, (45 reviews)
"Nice place for a weekend. Good price and everything we needed"
United States
Devan M.
$159 nightly
The price is $159
Nov 16 - Nov 17
Total with taxes and fees
Recently updated apartment in a Triplex close to Spire 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

An outdoor patio with a fire pit, seating, and string lights.
Hampton Inn Madison

Hampton Inn Madison

Hampton Inn Madison
Madison

10/10 Excellent

The workout facility was very nice. The store in the lobby was well stocked. The Bistro was very nice and had family friendly prices.
United States
John M
Reviewed January 1, 2025
Hampton Inn Madison

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 $127 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.

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.

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