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Check prices for these dates

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

Our top choices for Madison holiday 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
The price is £153
includes taxes & fees
19 Nov - 20 Nov
Romantic Woodside Cabin | Hot Tub & Fire Pit
A bedroom with a bed, nightstands, a lamp, and curtains.

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
The price is £186
includes taxes & fees
17 Nov - 18 Nov
The Blue Grape: Dog-Friendly Wine Country Home, King Bed & Private Deck
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, (23 reviews)
"Nice stay"
United States
Michael M.
The price is £190
includes taxes & fees
15 Nov - 16 Nov
LemonDrop Lake-Front Cottage
A living room with a beige sofa, a coffee table, a side table, a fireplace, and a television mounted on the wall.

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.
The price is £214
includes taxes & fees
17 Nov - 18 Nov
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.
The price is £198
includes taxes & fees
11 Nov - 12 Nov
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.
The price is £184
includes taxes & fees
15 Nov - 16 Nov
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
The price is £177
includes taxes & fees
15 Nov - 16 Nov
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
The price is £194
includes taxes & fees
15 Nov - 16 Nov
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.
The price is £228
includes taxes & fees
11 Nov - 12 Nov
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.
The price is £325
includes taxes & fees
15 Nov - 16 Nov
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.
The price is £230
includes taxes & fees
9 Dec - 10 Dec
Charming 2-bedroom house in delightful Madison with AC
A person performing a yoga pose on a mat outdoors with a body of water in the background.

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.
The price is £197
includes taxes & fees
12 Nov - 13 Nov
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
The price is £235
includes taxes & fees
12 Nov - 13 Nov
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.
The price is £137
includes taxes & fees
22 Nov - 23 Nov
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.
The price is £148
includes taxes & fees
15 Nov - 16 Nov
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
The price is £151
includes taxes & fees
11 Nov - 12 Nov
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.
The price is £96
includes taxes & fees
16 Nov - 17 Nov
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.
The price is £193
includes taxes & fees
13 Nov - 14 Nov
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.
The price is £117
includes taxes & fees
13 Nov - 14 Nov
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.
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

A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and a well-lit facade.
Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG
Madison

10/10 Excellent

Very nice hotel great room and nice staff also had an excellent breakfast I only had one issue which should not reflect on the hotel there was a very large religious gathering of people/familes with beards and bonnets who spent a lot of time slamming doors but this doesn’t reflect on it being a great hotel just unlucky with booking time
United Kingdom
steven
Reviewed September 22, 2025
Holiday Inn Express & Suites Madison by IHG

Find out more about Madison

Everything you need to know about Madison holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madison holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison holiday rentals we have selected for you start as low as £95 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison holiday 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 holiday.

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 holiday rental in Madison?

Yes, there are holiday rentals in Madison close to Rabbit Run Community Arts Association, or you can select a more secluded option if you're looking for a relaxing stay. Madison is known for its wineries and theatres. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Madison has to offer?

Charming 2-bedroom house in delightful Madison with AC: This highly rated holiday home rental in Madison is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday 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 holiday rentals will I find in Madison?

With 38 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.