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.

Guest suite in Sun Prairie

4.88 out of 5 average rating, 336 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) 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.

4.95 out of 5 average rating, 376 reviews

Guest suite in Madison

Cottage Suite + Whirlpool Tub.

This Suite is perfect for 1-4 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond./Bodywash

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 605 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.

4.97 out of 5 average rating, 186 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.

4.96 out of 5 average rating, 127 reviews

Apartment in McFarland

#302 Private Apartment in Historic McFarland House

This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1856 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

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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 stars1 week 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!

4.97 out of 5 average rating, 490 reviews

Spacious private level with garden view and more.

BeverlyRating, 5 stars1 week ago

Outstanding Airbnb. The room was spacious, fridge was stocked with bottled water and soda. Nice little kitchenette area. Cozy wonderful sitting area near the fire place looking out at gorgeous serene gardens. We spent hours on the patio! Bed was super comfy and quality linens were appreciated. Clean bathroom with toiletries and thick large towels. Loved all the art work, stained glass and collection of books. Guest book with recommendations was very thorough. Looking forward to returning next summer! Greg and Fred were great hosts!!

4.94 out of 5 average rating, 286 reviews

Private Suite on Park & Bike Trail

NicholasRating, 5 stars2 weeks ago

Excellent hosts. Had a very nice cat. (It’s not aloud in the rooms I stayed at due to possibly allergic guests)

4.91 out of 5 average rating, 249 reviews

Cozy 1-bedroom steps from Lake Monona

TosiRating, 5 stars2 weeks ago

This is a beautiful area to walk in and visit, a quiet neighborhood steps from the lake and parks, Michael’s place is minimalist and you will need to eat out for your meals but there are walkable eateries nearby. Very comfy bed too!

4.97 out of 5 average rating, 812 reviews

Private Garden Level Guest Suite

RebeccaRating, 5 stars1 day 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.

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!

4.98 out of 5 average rating, 314 reviews

private, sunny lower level

LisaRating, 5 stars6 days ago

Jason is a welcoming and gracious host. He made us feel very much at home and was always responsive. The basement apartment worked great! Jason clearly put a lot of thought into designing a cozy place. There’s plenty of space and plenty of natural light. We also appreciated both having a kitchenette and access to the main kitchen. The location made it easy to get to the places we came to Madison to see, and it was also close to plenty of restaurants and other amenities. We would definitely stay here again!