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South 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 South Madison vacation rentals

A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

1. Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (56 reviews)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
$436 nightly
The price is $494
Oct 12 - Oct 13
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (188 reviews)
"The Dylan was a great location for us and we were very pleased with the garage parking, new modern finishes and the communication of the host. The unit had everything we needed for a super comfortable stay including a full kitchen and washer/dryer. No wasted space. Good arrangement in this two bedroom unit for 2 couples. Would stay here again and recommend."
United States
Debbie
$112 nightly
The price is $129
Nov 1 - Nov 2
Total with taxes and fees
The Dylin
An outdoor patio with a brick grill and seating area.

3. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
$147 nightly
The price is $167
Nov 1 - Nov 2
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

4. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (54 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
$118 nightly
The price is $125
Oct 14 - Oct 15
Total with taxes and fees
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

5. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$172 nightly
The price is $195
Oct 4 - Oct 5
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

6. King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
$195 nightly
The price is $221
Oct 11 - Oct 12
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

7. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
$250 nightly
The price is $266
Oct 5 - Oct 6
Total with taxes and fees
Studio Apartment at Cannery Square
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

8. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (55 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
$313 nightly
The price is $352
Oct 19 - Oct 20
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

9. Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful place, great stay."
United States
Thomas D.
$259 nightly
The price is $286
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
An outdoor seating area with wicker furniture and a central fire feature.

10. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
$217 nightly
The price is $251
Nov 1 - Nov 2
Total with taxes and fees
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

11. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (32 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
$222 nightly
The price is $252
Oct 4 - Oct 5
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
A modern kitchen with a dishwasher, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

12. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (30 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
$315 nightly
The price is $354
Oct 6 - Oct 7
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
A gym with treadmills, elliptical machines, and free weights.

13. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great little town to stay the night. Woke early 5:30 am to tow truck towing cars in front lot. We luckily parked in back lot as instructed. Other than the noise of this unfortunate event, we enjoyed our stay. Loved the town and many places to walk to. Pizza place was amazing!"
United States
Cheryl B.
$244 nightly
The price is $275
Oct 28 - Oct 29
Total with taxes and fees
Studio Apartment at Cannery Square
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

14. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
$399 nightly
The price is $453
Oct 28 - Oct 29
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A small cabin with a wooden deck and a glass door.

15. Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (52 reviews)
"Thank you for a peaceful stay, we came from Arizona to host my mothers memorial and the comfort and relaxation was well needed, plus it was big enough to have my kids spend time with us as well. Thank you for everything!"
United States
Kelly T.
$209 nightly
The price is $221
Oct 5 - Oct 6
Total with taxes and fees
Log Cabin at Lake Koshkonong - “The Overlook”
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

16. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (45 reviews)
"Great place!"
United States
Robert F.
$489 nightly
The price is $565
Oct 8 - Oct 9
Total with taxes and fees
Doty ★ Walk to Everything -Hotel Quality- Downtown
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

17. Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
$224 nightly
The price is $248
Oct 11 - Oct 12
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
A modern kitchen with a refrigerator, microwave, and bar stools.

18. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 reviews)
"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."
United States
Sha'Vonne G.
$360 nightly
The price is $405
Oct 5 - Oct 6
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!
A spacious living room with a fireplace, comfortable seating, and a television mounted above it.

19. Premium 3BR | Quick to Downtown

Premium 3BR | Quick to Downtown
Fitchburg
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful place with lots of room. "
United States
Brenda B.
$725 nightly
The price is $823
Oct 5 - Oct 6
Total with taxes and fees
Premium 3BR | Quick to Downtown
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

20. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (27 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
$254 nightly
The price is $281
Nov 1 - Nov 2
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace
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 South Madison Hotel Reviews

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"Great location and value."
Nicole 3-night trip
Posted 10 hours ago
The Madison Concourse Hotel and Governor's Club

Find out more about South Madison

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

South Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South 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 South 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 $125 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 South Madison rentals

At Expedia, we put the best South 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 South 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 South 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 South 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.

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