Vacation rentals in Shorewood Hills

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Top-rated vacation rentals in Shorewood Hills

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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 18 – 25

ﺩ.ﺇ415 per night

Guest favorite

Home in Madison

4.95 out of 5 average rating, 154 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 ;)

Dec 11 – 18

ﺩ.ﺇ513 per night

Guest favorite

Guest suite in Madison

4.97 out of 5 average rating, 296 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

ﺩ.ﺇ355 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

Sep 18 – 25

ﺩ.ﺇ518 per night

Guest favorite

Guest suite in Middleton

5.0 out of 5 average rating, 114 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.

Sep 20 – 27

ﺩ.ﺇ339 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.

Aug 1 – 8

ﺩ.ﺇ525 per night

Guest favorite

Home in Madison

4.99 out of 5 average rating, 300 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

Oct 2 – 9

ﺩ.ﺇ661 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 16 – 23

ﺩ.ﺇ605 per night

Guest favorite

Guest suite in Sun Prairie

4.89 out of 5 average rating, 245 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.

Jan 8 – 15

ﺩ.ﺇ319 per night

Guest favorite

Home in Madison

4.98 out of 5 average rating, 105 reviews

Close to UW! 4 Bdrms, Walk to restaurants

- Clean, uncluttered home - Chef's kitchen, 2 separate living areas, 4 bedrooms, 2 bathrooms and a dining room - Walkable, historic neighborhood. Restaurants, coffee shops, and a neighborhood bar all within 2 blocks. - Covered front porch and open back deck - Off-street parking for up to 3 cars - 1 mile (20 min. walk) from University of Wisconsin-Madison campus and Camp Randall - 2 miles from downtown Madison - Family friendly amenities (toys, outdoor playground)

Aug 23 – 28

ﺩ.ﺇ1,558 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

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.

May 30 – Jun 6

ﺩ.ﺇ622 per night

Guest favorite

Guesthouse in Stoughton

4.94 out of 5 average rating, 330 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 5 – 12

ﺩ.ﺇ339 per night