Holiday houses in Shorewood Hills

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Top-rated holiday rentals in Shorewood Hills

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A welcoming living area features a mix of seating options, including a white leather couch and two armchairs in contrasting colors. A wooden coffee table sits in the center, complemented by a decorative plant. Natural light illuminates the room, enhancing its cozy atmosphere.
Home in Spring Harbor
4.98 out of 5 average rating, 83 reviews

Cottage gem: Spotless, secluded & bring the dog!

Bring the whole family - furry friends, too! - to relax beneath towering trees in our quiet cottage on Madison's west side. Cooks love the refreshed kitchen with all the tools! Enjoy a remodeled bathroom, Mid Mod furnishings & comfy beds. Grill & dine on a spacious deck and enjoy the wooded (unfenced) yard. Dog owners: Up to 2 well-behaved pooches are welcome with $125 pet fee at booking; please observe rules so we can keep hosting 4-legged friends and maintain a pristine home for all guests.

Top Guest favourite
The bedroom features a queen bed with a patterned blanket, complemented by two bedside lamps. Natural light enters through a window adorned with plants. A simple piece of wall art adds a touch of decor, while a wooden chair is positioned nearby.
Guest suite in Eken Park
4.97 out of 5 average rating, 391 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.

Top Guest favourite
A bright living area features two gray sofas and two striped armchairs arranged around a coffee table. Natural light floods the space through large windows, highlighting the vaulted ceiling and minimalist decor. A small side table completes the seating arrangement.
Home in Madison
5 out of 5 average rating, 31 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.

Superhost
A spacious living area features a mounted flatscreen TV above a mid-century modern stereo console. Two armchairs are positioned around a round coffee table, creating an inviting space. Natural light filters through large windows dressed with light curtains, enhancing the room's atmosphere.
Home in Madison
4.88 out of 5 average rating, 371 reviews

Grooviest | Quiet | Close | Upscale MCM | Records!

• NEWLY RENOVATED SPACE. • Two floor upper unit in a private home • Private backyard with patio & fire pit • Flatscreen TV in living room with Chromcast and Antenna. • Luxury Mid Century Modern Stereo Console bluetooth • 12+ classic albums to listen to (jazz, rock, classical) More Avail Locally! • Access to thousands of albums at several nearby vintage vinyl stores • Electric fireplace w/ multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked, Keurig • Vintage Bar Cart

Guest favourite
An A-frame interior showcases a spiral staircase leading to the loft, surrounded by natural wood and brick accents. A large television is mounted above a fireplace, complemented by decorative plants and a wall clock. Colorful patterns can be seen in the ceiling lights.
Home in Arbor Hills
4.95 out of 5 average rating, 184 reviews

ONE OF A KIND vacation rental with a view

Arbor Hill House - Unique A-frame vacation rental perched atop a hill with great views overlooking the Beltline, UW Arboretum and the city of Madison. Excellent central location with easy access to all of Madison and surrounding areas. I'll be happy to do whatever I can to make your stay a pleasant one. Please keep things clean and be respectful. The home should not be used for parties or events. If you have any questions please feel free to ask. I look forward to sharing my home with you.

Top Guest favourite
A spacious living room is presented with large windows allowing natural light. A comfortable couch with decorative pillows faces a wooden coffee table, surrounded by two accent chairs. A woven stool adds texture, while standing lamps provide additional illumination. Minimalist art decorates the wall.
Bungalow in Westmorland
4.96 out of 5 average rating, 71 reviews

Sunny, spacious home, conveniently located.

Completely renovated, sunny and spacious bungalow in a conveniently-located, residential neighborhood. Newly refurnished for your enjoyment. Large living room, dining room, and full kitchen. Two bedrooms- one queen size bed, one full size bed and a queen sleeper-sofa. There is Wi-Fi, cable and Roku TV. Child- and family-friendly, with equipment and toys for the little ones. Quick and easy access to major roads and highways. 5-10 minutes from campus and downtown, 15 minutes from Epic.

Top Guest favourite
A spacious studio featuring two green upholstered benches arranged on a decorative area rug. Natural light floods the room through skylights, illuminating the cozy sleeping area with a large bed and a dining nook equipped with a small table and chairs.
Guest suite in Middleton
4.98 out of 5 average rating, 226 reviews

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.

Top Guest favourite
A living room is depicted with hardwood floors and a warm atmosphere. A black leather sofa is paired with a wooden coffee table, while a textured area rug adds comfort. A decorative fireplace and wall art complement the space, which opens to a dining area in the background.
Apartment in Madison
4.97 out of 5 average rating, 158 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.

Guest favourite
Home in Middleton
4.94 out of 5 average rating, 17 reviews

The Wright Balance

Find your “Wright Balance” in this cozy lower-level retreat in Middleton Hills, known for its Frank Lloyd Wright–inspired architecture. With a private entrance, two bedrooms, and a full bath, it’s perfect for business, family, or exploring. Just minutes from Madison and UW, yet steps from prairies, wetlands, and trails. Restaurants, a café, and grocery store are all within walking distance—balance convenience with natural beauty.

Superhost
A cozy sleeping area features a spacious bed with white linens and a gray blanket. A desk and chair are positioned near a small window, while a mini-fridge offers convenience. A light-colored artwork depicting a beach is displayed on the wall.
Apartment in Marquette
4.8 out of 5 average rating, 41 reviews

#412

Before booking this unit please be aware there is an apartment above this one with wood floors. If you are sensitive to sound/noise this may not be a good fit. 1 queen bed, a private bathroom with a shower, and a workspace. . This unit is located in the lower level of the building. Appliances: Fridge, Microwave, Coffee Pot (included: coffee grounds, coffee creamer, disposable coffee cups, sugar packets, assortment of tea bags.).

Top Guest favourite
A spacious dining area features a rectangular table set with a checkered tablecloth and surrounded by blue chairs. A decorative arrangement of flowers sits at the center of the table, and a patterned rug adds warmth to the space. Shelving with books is visible in the background.
Guest suite in Madison
4.94 out of 5 average rating, 395 reviews

Far Westside Home Away From Home

Your own 820 square foot space with full bathroom. Located 6.2 miles from the UW Madison. Inside, you will find a bedroom with a queen bed, a queen size comfortable hide-a-bed sofa, a 42" HDTV, a kitchenette w/a dining room table, a mini-fridge, an elliptical, and a library. To see a video of the space go to YouTube and search on “v=hDgEasBTxoA” (cut and paste recommended). ZTRHP1-2020-00044

Top Guest favourite
Apartment in Madison
5 out of 5 average rating, 14 reviews

Downtown Historic 2 BR Unit O.

Historic charm meets modern comfort in the heart of downtown. This bright, spacious two bedroom unit features a full kitchen and plenty of storage. Enjoy access to a shared rooftop deck overlooking top restaurants. Hosted by Voyageur Stays—a locally owned, husband-and-wife-run company passionate about handcrafted, thoughtfully curated spaces. Second floor walk-up. Paid parking.

Popular amenities for Shorewood Hills holiday rentals

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  4. Dane County
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