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South Madison Vacation Rentals

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Our top choices for South Madison vacation rentals

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (211 reviews)
"Good location"
United States
ANCA
The price is CA $156
CA $180 total
includes taxes & fees
Nov 19 - Nov 20
The Dylin

2. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (59 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
The price is CA $120
CA $162 total
includes taxes & fees
Dec 1 - Dec 2
A Room with a View

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

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.4 out of 10, Very good, (7 reviews)
"Great place for a stay."
United States
Andy D.
The price is CA $207
CA $250 total
includes taxes & fees
Nov 15 - Nov 16
King Suite | Free Breakfast. Pool and Hot Tub

4. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is CA $230
CA $285 total
includes taxes & fees
Nov 12 - Nov 13
Pool with Slide. Great for Business Travelers!

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
The price is CA $263
CA $326 total
includes taxes & fees
Nov 12 - Nov 13
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

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

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (48 reviews)
"Great stay! Very close to everything downtown."
United States
Garrett M.
The price is CA $270
CA $450 total
includes taxes & fees
Nov 16 - Nov 17
Doty ★ Walk to Everything -Hotel Quality- Downtown

7. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is CA $114
CA $360 total
includes taxes & fees
Nov 15 - Nov 16
Studio Apartment at Cannery Square

8. 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.
The price is CA $288
CA $368 total
includes taxes & fees
Dec 6 - Dec 7
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

9. 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)
"Great and easy stay! The place was comfortable and inviting. Would stay again!"
United States
Taylor S.
The price is CA $179
CA $478 total
includes taxes & fees
Nov 29 - Nov 30
2 Bed, 2 Bath Apartment at Cannery Square

10. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (31 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is CA $179
CA $478 total
includes taxes & fees
Nov 11 - Nov 12
2 Bed, 2 Bath Apartment at Cannery Square

11. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great location - able to walk to many stores and restaurants. Spacious for a studio and very quiet."
United States
Martha T.
The price is CA $164
CA $374 total
includes taxes & fees
Nov 15 - Nov 16
Studio Apartment at Cannery Square

12. 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, (34 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.
The price is CA $184
CA $345 total
includes taxes & fees
Nov 21 - Nov 22
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

13. 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.
The price is CA $178
CA $375 total
includes taxes & fees
Nov 9 - Nov 10
Charming Downtown Two Bedroom w/ Fireplace

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)
"Everything was very nice"
United States
Anonymous traveller
The price is CA $209
CA $624 total
includes taxes & fees
Nov 9 - Nov 10
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

15. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (43 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.
The price is CA $273
CA $550 total
includes taxes & fees
Nov 9 - Nov 10
2 Bedroom Apartment Downtown Sun Prairie!

16. Charming 3-bedroom house on Madison's Eastside! Close to everything!

Charming 3-bedroom house on Madison's Eastside! Close to everything!
Madison
The price is CA $509
CA $816 total
includes taxes & fees
Nov 9 - Nov 10
Charming 3-bedroom house on Madison's Eastside! Close to everything!

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.
The price is CA $243
CA $376 total
includes taxes & fees
Dec 2 - Dec 3
Escape to tranquility – your countryside haven, and at times with a horse or two

18. Free Breakfast Pool & Hot Tub. Near East Towne Mall!

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Madison
10.0 out of 10, Exceptional, (1 review)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is CA $496
CA $618 total
includes taxes & fees
Nov 29 - Nov 30
Free Breakfast Pool & Hot Tub. Near East Towne Mall!

19. Spacious 3-bedroom apartment in Downtown Stoughton

Spacious 3-bedroom apartment in Downtown Stoughton
Stoughton
10.0 out of 10, Exceptional, (1 review)
"The stay was very clean and comfortable. Location was super convenient—you’re right downtown surrounded by cute shops and restaurants. Grayson was so communicative and was such a responsive and accommodating host. Will absolutely return if we ever find ourselves needing to stay in Stoughton again. Highly recommend!"
United States
Laura M.
The price is CA $258
CA $537 total
includes taxes & fees
Nov 30 - Dec 1
Spacious 3-bedroom apartment in Downtown Stoughton

20. Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (26 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is CA $494
CA $812 total
includes taxes & fees
Nov 9 - Nov 10
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
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

Find out more about South Madison

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Madison. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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