Vacation rentals with outdoor seating in Madison

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Top-rated outdoor seating rentals in Madison

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Guest favorite

Guesthouse in Mount Horeb

4.97 out of 5 average rating, 544 reviews

Cool, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful space that features tall ceilings and an open design--giving it a loft feel with an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs included in your online reservation, must be leashed when outside, and kenneled in your absence.

Jun 23 – 30

G$23,616 GYD per night

Guest favorite

Loft in Madison

4.88 out of 5 average rating, 373 reviews

Cape Cod Loft, High-Speed internet + King bed

Welcome! This property is on Madison’s funky-up & coming East side. Quiet, conveniently located residential neighborhood with great neighbors & free street parking. The upstairs unit is a private guest-dedicated suite with it's own kitchenette & side entrance. GPS: Meriter Hospital, St Mary's Hospital, UW Hospital- 15 min Dane County Airport- 7 min. Wisconsin State Capitol- 12 min. Ulbrich Botanical Garden's- 5 min. Camp Randall Stadium- 16 min. *Bike *Lyft *Uber *Nearby public bus stops

Sep 27 – Oct 4

G$30,336 GYD per night

Guest favorite

Home in Madison

4.95 out of 5 average rating, 159 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$27,510 GYD per night

Guest favorite

Apartment in New Glarus

5.0 out of 5 average rating, 340 reviews

The Hideout In Downtown New Glarus

Modern 1 bedroom apt. with a spacious outdoor deck on the second floor of the historic Citizen's Bank building built in 1910 and located in the heart of downtown New Glarus. You will be steps away from restaurants, pubs, shops, park, bike path, community pool, and annual festivals. This newly remodeled apartment has beautiful quartz countertop & island, and original wood floors. Newly installed large windows allow for ample natural light. Check out The Hideaway if you need a 2 bedroom rental.

Aug 9 – 16

G$31,778 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

Mar 6 – 13

G$31,799 GYD per night

Guest favorite

Home in Madison

4.88 out of 5 average rating, 210 reviews

Private apartment -2 Beds, Kitchen Office, Sunroom

COVID CLEANED Private Garden Apartment. Feel at home in your private lower level living space. Our home is surrounded by beautiful landscaped gardens and patios. We are located near the lake, on the lake bike loop, in the heart of Madison. Relax outside, enjoy dinner on the patio or have a bonfire. Venture out on a bike ride to the farmer's market on the Capital Square, or visit Monona Terrace, State Street, Olbrich Gardens or the Alliant Energy Center; just a short distance away.

Jul 25 – Aug 1

G$29,907 GYD per night

Guest favorite

Home in Madison

4.99 out of 5 average rating, 301 reviews

Beautiful 3 Bedroom Apartment, Kitchen, Fireplace

Private lower level 1600sq ft apartment. Steps away from TPC Wisconsin! Follow the path to the back of the main house, here you'll find a beautiful space with large windows and plenty of natural light. Enjoy the warm gas fireplace, large flat screen TV. Make meals in the generous farmhouse kitchen. Sorry no full-size oven. Relax on the paved patio overlooking the wetlands and listen to many birds. Just a 5 min drive to the airport and close to downtown. TPC WISCONSIN OPENING 8/2023

Sep 22 – 29

G$39,098 GYD per night

Guest favorite

Guest suite in Sun Prairie

4.89 out of 5 average rating, 248 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.

Apr 8 – 15

G$18,186 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!

Aug 23 – 30

G$32,053 GYD per night

Guest favorite

Tiny home in Darlington

4.98 out of 5 average rating, 248 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.

Oct 4 – 11

G$20,118 GYD per night

Guest favorite

Guest suite in Madison

4.98 out of 5 average rating, 554 reviews

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

We are located in a unique pocket of downtown Madison, directly across from Brittingham Park, Monona Bay, Brittingham Boat Rental & a bike/walking/running path. We are a short walk from UW-Madison, Hospitals, State Street & the Capitol. You will love our welcoming neighborhood! We have a friendly dog, Bella, who stay upstairs with us, but you could see her wandering outside. We have been inspected and are licensed with the City of Madison. ZTRHP1-2020-00027.

Jun 16 – 23

G$36,918 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.

Dec 6 – 13

G$19,278 GYD per night