Holiday rentals in Shorewood Hills

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Top-rated holiday rentals in Shorewood Hills

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Top guest favourite
Home in Regent
4.98 out of 5 average rating, 261 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.

Top guest favourite
A cozy outdoor space is featured with a wooden pergola providing shade, surrounded by blue siding. Seating includes two cushioned chairs and a swing chair, all arranged around a fire table set on a patterned rug, enhancing the inviting atmosphere.
Guest suite in Madison
4.95 out of 5 average rating, 409 reviews

Cottage Suite + Jacuzzi Tub & Sauna

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

Top guest favourite
Flat in Madison
4.97 out of 5 average rating, 33 reviews

The Wilson Unit D | Spacious Renovated Studio

Located within The Wilson, this spacious third-floor studio blends historic charm with modern updates in the heart of downtown. Enjoy a renovated kitchen with dishwasher and a renovated bath. Situated on the alley side, occasional early-morning city activity may be heard. Guests have access to the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtfully curated spaces. Third-floor walk-up with paid parking nearby.

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, 398 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 room features hardwood floors and large windows, allowing natural light to fill the space. A comfortable white sectional sofa and a dark armchair are arranged around a coffee table, with a striped area rug adding warmth. Wall art and lamps provide additional charm.
Home in Regent
4.98 out of 5 average rating, 124 reviews

Close to UW, 4 Bdrms, Walkable Neighborhood

Discover Madison at Bucky’s Retreat! Located in the walkable Regent neighborhood, our clean, family-friendly 1,800SF 4-bedroom home is minutes from UW-Madison, Camp Randall (20 min. walk), and downtown. Enjoy nearby restaurants, coffee shops, and a neighborhood bar just 2 blocks away. We have a well-stocked chef’s kitchen and the covered front porch is perfect for relaxing. Off-street parking for up to 3 vehicles. Note: This is our primary home, shared with guests while we travel. No pets.

Top guest favourite
Home in Marquette
4.97 out of 5 average rating, 234 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).

Guest favourite
A serene outdoor patio area is shown, featuring a cobblestone surface surrounded by well-maintained gardens and tall, manicured hedges. A central fountain adds visual interest, while a dining table and chairs invite relaxation. Potted plants and seasonal flowers enhance the garden's charm.
Home in Madison
4.88 out of 5 average rating, 294 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.

Top guest favourite
A cozy living room features a plush orange sofa paired with two gray armchairs. A wooden coffee table is positioned in front, displaying magazines. The room is illuminated by natural light through three windows, and a flat-screen TV is mounted above a decorative fireplace.
Flat in Oregon
4.96 out of 5 average rating, 109 reviews

Downtown Apt - Steps to Coffee & Sushi!

* Be sure to check out our winter extended stay discounts for 3+ nights! * Welcome to historic downtown Oregon! Step into the past while enjoying modern comfort in this beautiful space, which once housed our 1st library! Just steps away from locally owned coffee and gift shops, a wine reserve, and amazing restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!

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, 236 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 spacious studio is illuminated by natural light through large windows. A cozy seating area with a yellow sofa is positioned next to a modern entertainment unit. A patterned area rug complements the minimalist décor, and a comfortable sleeping area with a well-made bed is visible.
Flat in Madison
4.93 out of 5 average rating, 58 reviews

The Wilson L | Quiet Corner Studio with Vanity

Located within The Wilson, this thoughtfully designed second-floor corner studio sits at the back of the building for a quiet, tucked-away feel. Historic charm meets refined comfort, and a dedicated vanity offers a convenient space for getting ready. Guests enjoy access to the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtfully curated spaces. Second-floor walk-up and paid parking nearby.

Top guest favourite
Flat in Madison
4.98 out of 5 average rating, 164 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.

Top guest favourite
Guest suite in Madison
4.94 out of 5 average rating, 403 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, living room w/a queen size comfortable sofa bed, a 54”HDTV, a kitchenette (not a full kitchen) w/a dining room table, a mini-fridge, 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

Popular amenities for Shorewood Hills holiday rentals

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  2. United States
  3. Wisconsin
  4. Dane County
  5. Shorewood Hills