Vacation rentals in Sun Prairie

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Top-rated vacation rentals in Sun Prairie

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Guest favorite

Home in Madison

4.95 out of 5 average rating, 155 reviews

Grooviest | Quiet | Close | Upscale MCM | Records!

• ALL NEW RENOVATION, BRAND NEW LINENS, TOWELS, ETC • Two floor private home • Private backyard with patio & fire pits • Two TVs, one in living room, one in dining room • Luxury Mid Century Modern Stereo Console with records, bluetooth • Over 70 classic albums to listen to (jazz, rock, classical, eclectic) • Access to over 1000 classic albums at our downtown Music Studio • Electric fireplace with multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked • Vintage Bar Cart ;)

Nov 5 – 12

G$27,432 GYD per night

Guest favorite

Guest suite in Madison

4.97 out of 5 average rating, 297 reviews

Private & Clean Apartment Near Downtown & Airport

Private, sunny basement unit with separate entry accessible by keycode. 1 bedroom (queen), full bath, sitting area (2 twins/king bed), desk, WI-FI, TV, mini fridge, microwave, & coffee/tea. On street parking. Kid friendly! Note: We live with kids above the apartment - you will hear us walking around & some water pipes. 2-4 mi from Airport, Capitol, & UW Campus. Walk to brunch, pub, jazz lounge, bubble tea, grocery store, park, & bike path. Licensed by City & State. Paying all taxes & fees.

Aug 14 – 21

G$22,842 GYD per night

Guest favorite

Guest suite in Madison

4.99 out of 5 average rating, 149 reviews

Peaceful 2 BR/1 BA w/ patio, firepit & pool table

• 1400 sq.ft. lower level suite • Private backyard with patio & gas fire pit • Two TVs • Electric fireplace • Pool and Air hockey table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • Onsite parking in driveway for one vehicle • Ample street parking • 16-min drive to UW campus and downtown • 9-min drive to the airport • 6-min drive to shopping and restaurants • Extremely safe neighborhood • License No. LICHMD-2022-00079 • Zone Permit ZTRHP1-2022-00005

Apr 2 – 9

G$32,386 GYD per night

Guest favorite

Guest suite in Middleton

5.0 out of 5 average rating, 115 reviews

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with two skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house but has its own outdoor entrance and is soundproofed for privacy. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Oct 8 – 15

G$18,327 GYD per night

Guest favorite

Guest suite in Sun Prairie

4.89 out of 5 average rating, 247 reviews

Entire Countryside Garden Suite, Peaceful Retreat

Welcome to our home! We have upgraded our Garden Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Feb 4 – 11

G$18,134 GYD per night

Guest favorite

Guesthouse in Madison

4.92 out of 5 average rating, 245 reviews

Historic guesthouse near downtown, hospital and UW

Featured on the National Register of Historic Places, this unique 1916 “granny cottage" stands behind our home in the gorgeous Village of Shorewood Hills. Centrally located, we are just a few walkable blocks from UW Hospital and Picnic Point, and walking/biking distance from UW, the Capitol, Hilldale Shopping Mall, Whole Foods and plenty of restaurants. Because we are in a quiet neighborhood, we have a 3 guest maximum. This is a place to retreat and relax and enjoy the best of Madison.

Sep 12 – 19

G$32,032 GYD per night

Guest favorite

Cabin in Fox Lake

4.95 out of 5 average rating, 122 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing by walking to the lake out your back door! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 fee/stay.

Dec 16 – 23

G$22,351 GYD per night

Guest favorite

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 307 reviews

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

Feb 19 – 26

G$31,961 GYD per night

Guest favorite

Tiny home in Darlington

4.98 out of 5 average rating, 246 reviews

The Bower- Peaceful farm stay getaway.

Thank you for checking out The Bower at Arbor Crest Acres! We would be happy to host you! This is our 5th year hosting and our 2nd tiny cottage. Our farmette is conveniently located 2 miles from town, set off the road, and through the woods. The Bower is just inside our property on the edge of the woods. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

Dec 31 – Jan 7

G$20,061 GYD per night

Guest favorite

Apartment in Town of Sun Prairie

4.86 out of 5 average rating, 147 reviews

Whoa! Serene Country Garden Level Apartment

One bedroom, 1200 sq.ft. apartment in large, modern country home has full kitchen and private bathroom. The property is also the home of Blue Haven Stables, a working show horse stable. The apartment was recently remodeled and has beautiful views of fields and woods. Quiet. Private horse riding lessons available. Comfortable for two people. Just 30 minutes away from two downhill ski hills and 2 miles away from a county cross country ski park.

Aug 21 – 28

G$28,295 GYD per night

Guest favorite

Apartment in Madison

4.96 out of 5 average rating, 104 reviews

Private entry flat near Atwood neighborhood

No cleaning fee!! Enjoy your visit to Madison in this sunny one bedroom apartment with private entrance and off street parking. It's great location is within walking distance to the Schenk/Atwood neighborhood, with numerous restaurants, cafes and music venues. Within 2 miles of the state capitol, Monona Terrace, and 3 miles from the airport, Kohl Center and Camp Randall. Perfectly suited for couples, solo adventurers, or business travelers.

May 24 – 31

G$31,770 GYD per night

Guest favorite

Guesthouse in Stoughton

4.94 out of 5 average rating, 331 reviews

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.

Mar 6 – 13

G$19,223 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Sun Prairie vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Sun Prairie's top sights

Marcus Palace Cinema14 locals recommend

Woodman's Food Market6 locals recommend

Costco Wholesale5 locals recommend

Nitty Gritty-Sun Prairie4 locals recommend

Full Mile Beer Company & Kitchen3 locals recommend

Target4 locals recommend

Other great vacation rentals in Sun Prairie

Guest favorite

Cabin in Edgerton

4.89 out of 5 average rating, 197 reviews

The Overlook on Lake Koshkonong - Custom Log Cabin

Nov 24 – Dec 1

G$21,594 GYD per night

Guest favorite

Home in Madison

4.95 out of 5 average rating, 304 reviews

Cottage Suite + Whirlpool Tub.

Feb 26 – Mar 5

G$34,234 GYD per night

Guest favorite

Home in Madison

4.99 out of 5 average rating, 301 reviews

Beautiful 3 Bedroom Apartment, Kitchen, Fireplace

Oct 9 – 16

G$39,292 GYD per night

Guest favorite

Guest suite in Madison

4.98 out of 5 average rating, 551 reviews

DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus

May 12 – 17

G$30,125 GYD per night

Guest favorite

Apartment in Stoughton

4.96 out of 5 average rating, 113 reviews

Spacious Suite with Lake View

Jul 5 – 12

G$26,997 GYD per night

Guest favorite

Guesthouse in Belleville

4.98 out of 5 average rating, 211 reviews

Still Point Tiny House - (Zero Added Cleaning Fee)

Aug 29 – Sep 5

G$23,928 GYD per night

Guest favorite

Guest suite in Madison

4.95 out of 5 average rating, 208 reviews

Downtown Condo, 5 blocks from Capital, Btn 2 Lakes

Oct 7 – 14

G$28,316 GYD per night

Guest favorite

Apartment in DeForest

5.0 out of 5 average rating, 21 reviews

Kid & pet friendly. 25 minutes to capitol

Sep 10 – 17

G$21,232 GYD per night

Show all

Quick stats about vacation rentals in Sun Prairie

Total rentals
40 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
G$4,170 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Sun Prairie have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Sun Prairie. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sun Prairie have wifi?
Absolutely! We offer over 10 house rentals with wifi in Sun Prairie. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Sun Prairie?
Four-legged friends are welcome in Sun Prairie. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Sun Prairie?
Experience the best of Sun Prairie with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Sun Prairie?
Yes! Work meets play with ease at over 10 vacation rentals in Sun Prairie featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Sun Prairie?
Make yourself at home in Sun Prairie by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Vandenburg Heights, and over 50 vacation rentals in Smith''s Crossing.
What are the most popular amenities for House Rentals in Sun Prairie?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Sun Prairie?
Sun Prairie has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Sun Prairie

Top-rated vacation rentals in Sun Prairie

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Sun Prairie vacation rentals

Stay near Sun Prairie's top sights

Other great vacation rentals in Sun Prairie

Cabin in Edgerton

Home in Madison

Home in Madison

Guest suite in Madison

Apartment in Stoughton

Guesthouse in Belleville

Guest suite in Madison

Apartment in DeForest

Quick stats about vacation rentals in Sun Prairie

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Sun Prairie have air conditioning?

Do house rentals in Sun Prairie have wifi?

Are there pet-friendly vacation rentals in Sun Prairie?

How much does it cost to stay in house rentals in Sun Prairie?

Are there vacation rentals with a dedicated workspace in Sun Prairie?

Where should I stay in Sun Prairie?

What are the most popular amenities for House Rentals in Sun Prairie?

Are there family-friendly vacation rentals in Sun Prairie?

Destinations to explore