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South Madison Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for South Madison vacation rentals

A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (195 reviews)
"Good location"
United States
ANCA
$122 nightly
The price is $141
Nov 1 - Nov 2
Total with taxes and fees
The Dylin
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

2. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (56 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
$119 nightly
The price is $126
Oct 21 - Oct 22
Total with taxes and fees
A Room with a View
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.
$155 nightly
The price is $176
Nov 1 - Nov 2
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

4. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$182 nightly
The price is $207
Oct 18 - Oct 19
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.

5. 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
$207 nightly
The price is $235
Oct 25 - Oct 26
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.

6. 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 14 - Oct 15
Total with taxes and fees
Studio Apartment at Cannery Square
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

7. 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, (17 reviews)
"Beautiful place, great stay."
United States
Thomas D.
$260 nightly
The price is $287
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
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, (56 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
$316 nightly
The price is $356
Oct 19 - Oct 20
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
A gym with treadmills, elliptical machines, and free weights.

9. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
$244 nightly
The price is $275
Oct 28 - Oct 29
Total with taxes and fees
Studio Apartment at Cannery Square
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

10. 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, (33 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
$220 nightly
The price is $250
Oct 18 - Oct 19
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.

11. 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.
$314 nightly
The price is $353
Oct 14 - Oct 15
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
An outdoor seating area with wicker furniture and a central fire feature.

12. 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.
$236 nightly
The price is $272
Nov 1 - Nov 2
Total with taxes and fees
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

13. 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)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
$399 nightly
The price is $452
Nov 1 - Nov 2
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

14. 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.
$225 nightly
The price is $249
Oct 17 - Oct 18
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

15. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
$250 nightly
The price is $276
Nov 1 - Nov 2
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace
A small cabin with a wooden deck and a glass door.

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

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (53 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.
$260 nightly
The price is $274
Oct 14 - Oct 15
Total with taxes and fees
Log Cabin at Lake Koshkonong - “The Overlook”
A modern kitchen with a refrigerator, microwave, and bar stools.

17. 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 14 - Oct 15
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

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

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (46 reviews)
"Great place!"
United States
Robert F.
$489 nightly
The price is $565
Oct 14 - Oct 15
Total with taxes and fees
Doty ★ Walk to Everything -Hotel Quality- Downtown
A library with wooden bookshelves, a staircase, and a chandelier.

19. Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Spacious Condo: Historic Boutique Rental in Downtown Edgerton
Edgerton
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful.. just beautiful and right at the hert if town"
United States
Georgia S.
$267 nightly
The price is $276
Nov 8 - Nov 9
Total with taxes and fees
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
A two-story building with a brown roof, a wooden front door, and a window with the number 318.

20. Spacious 3-bedroom apartment in Downtown Stoughton

Spacious 3-bedroom apartment in Downtown Stoughton
Stoughton
$350 nightly
The price is $397
Oct 19 - Oct 20
Total with taxes and fees
Spacious 3-bedroom apartment in Downtown Stoughton
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

Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

10/10 Excellent
"Very clean and well maintained. Helpful staff ."
Mario 1-night trip
Posted less than an hour ago
Days Inn & Suites by Wyndham Madison

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 $126 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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