Vacation rentals in Shorewood Hills

4.92 out of 5 average rating, 307 reviews

Grooviest | Quiet | Close | Upscale MCM | Records!

• NEWLY RENOVATED SPACE. • Two floor upper unit in a private home • Private backyard with patio & fire pits • Flatscreen TV in living room with Chromcast and Antenna. • Luxury Mid Century Modern Stereo Console with records, bluetooth • Over 12 classic albums to listen to (jazz, rock, classical, eclectic) • Access to over 3000 classic albums at our downtown Music Studio • Electric fireplace w/ multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked, Keurig • Vintage Bar Cart

4.97 out of 5 average rating, 228 reviews

4-Bedroom Lathrop Home by UW/Camp Randall -Madison

Home steps to Camp Randall & a short walk to UW Madison! $375 / night (up to 5 guests); Extra guests $75 / night after the 5th guest ($1045 Nightly Rate up to 10 people max) $495 / night during Badger game days (up to 5 guests; $65 / night / guest after the 5th guest) Our back patio is also available to guests; however, please know that we use the garage & part of the driveway for tailgating with friends & family during Badgers football games. Cleaning Fee $150. No Pets or Smoking allowed.

4.91 out of 5 average rating, 172 reviews

Guest suite in Madison

Hospitality+Kitchen+Laundry+Gardens

Tastefully updated private suite on lower level of ranch. - KING bed plus twin bed, large bathroom, full kitchen, laundry W/D, work desk, dining table w/stools, comfortable furniture. Pristine clean. Close to grocery, many restaurants, parks, UW... Great for business needs (week and month long discounts!), moving to Madison, athletic events, visiting family... Tree lined street. Free parking. Owner lives on the property, but suite is private and not shared, as per Permit #ZTRHP1-2020-00004.

4.89 out of 5 average rating, 425 reviews

Guest suite in Madison

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. This 2nd floor unit is a private guest-dedicated suite with it's own kitchenette, full fridge & side entrance. Massage chair. GPS: Airport- 7 min. Wisconsin State Capitol- 12 min. Ulbrich Botanical Garden's- 5 min. Camp Randall Stadium- 16 min. Walkable to Starkweather Creek Trail. *Bike *Lyft *Uber *Nearby public bus stops

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 607 reviews

Cool, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and 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 reservation, must be leashed when outside.

5 out of 5 average rating, 27 reviews

Shorewood Hills Modern Home

Nestled in a sought-after neighborhood, this exquisite home showcases a perfect blend of contemporary design and functionality. Boasting a recent renovation, this modern gem offers an open-concept layout, luxurious master suite, a second master suite, two additional bedrooms, 5 total bathrooms, finished basement, three wet bars, workout room and so much more. Close to outdoor activities and vibrant amenities including fine dining, Camp Randall, Lake Mendota, Campus, etc.-all minutes by bike.

4.97 out of 5 average rating, 187 reviews

Lakeview Loft - Downtown Madison

Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).

4.93 out of 5 average rating, 260 reviews

Guesthouse in Madison

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.

4.98 out of 5 average rating, 191 reviews

Guest suite in Middleton

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a 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 and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

4.98 out of 5 average rating, 754 reviews

Tiny home in Darlington

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. 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.

4.92 out of 5 average rating, 167 reviews

Cozy, Sunny Artist's House (UW/Near West)

Our historic, art-filled home is close to the UW hospital and campus, but is located in a quiet and pretty neighborhood. Madison is known for its open-mindedness, amazing farm-to-table restaurant scene, walk- and bike-ability, and lots of performing arts for the small size of the city. We're Superhosts in our tenth year and we'd love to comfortably accommodate you. Please take the time to read our entire listing if you'll be staying with us to learn details about the house.

5 out of 5 average rating, 25 reviews

Apartment in Madison

Cozy Garden Apartment Near it All!

Stay in comfort at this peaceful and centrally-located place. Unwind in our cozy garden oasis after a day of exploring or visiting! This stylish well-lit studio basement apartment offers the perfect blend of comfort and convenience. Centrally located in a prime Madison Monroe Street neighborhood spot near shopping, dining, and UW or Edgewood sports venues, you'll have everything you need right at your fingertips.

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Other great vacation rentals in Shorewood Hills

4.92 out of 5 average rating, 283 reviews

1 sunny Yellow BR and lounge in Artist’s home!

WilliamRating, 5 stars2 weeks ago

I had a great stay! The house was clean and the hosts were very welcoming. The lounge space and coffee + tea were great touches. There were a lot of great paths and parks nearby and the hosts even had bikes to borrow. Couldn’t recommend enough!

5 out of 5 average rating, 19 reviews

Sweet, sunny room

DerekRating, 5 stars1 week ago

Greats host and a great place to stay. Will book again for future plans. Thank you for the wonderful hospitality.

4.91 out of 5 average rating, 252 reviews

Cozy 1-bedroom steps from Lake Monona

NikoRating, 5 stars1 week ago

This was a great place to stay - location is amazing, it was very easy to walk lots of places, parking was easy, getting in and out was easy, and the space was quiet and comfortable.

Superhost

4.75 out of 5 average rating, 226 reviews

Private room near downtown- The Madison room

GabrielRating, 5 stars2 weeks ago

Angela was extremely nice and the space was inviting. the room had everything and then some. my favorite part of the stay was the heated mattress pad. honestly one of the best experiences I've had with an Airbnb.

4.97 out of 5 average rating, 813 reviews

Private Garden Level Guest Suite

RebeccaRating, 5 stars3 days ago

Angie's place was clean and very comfortable with the best book assortment of any Airbnb I've ever stayed in! The neighborhood was quiet and there is a lovely park nearby that I walked around. So beautiful! Thank you for recommending Mercies for coffee and a quick breakfast nearby. It was great.

4.88 out of 5 average rating, 286 reviews

Private Upstairs Guest Suite - East Madison

MichaelRating, 5 stars3 weeks ago

Communication was very smooth and helpful. The place was well equipped and comfortable. Thank you, Jordan!

Private room in Middleton

4.95 out of 5 average rating, 147 reviews

Retreat in woods on Lake Mendota

MandyRating, 5 stars6 months ago

Glad to stay again with Michelle. She was flexible with our arrival time on a holiday and welcomed us personally. The place is clean and exactly what we needed. She even offered us hot water bottles for our bed as it was extremely cold out and we were chilled from the football game. Thank you for hosting us again!