Holiday houses in Whitefish Bay

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Top-rated holiday rentals in Whitefish Bay

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

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Guest favourite

Home in Shorewood

4.9 out of 5 average rating, 113 reviews

The Prospect House - Shorewood / Milwaukee, WI

From activities and attractions to fairs and festivals, Milwaukee, has something for everyone in your travel group! After each adventure-filled day, look forward to returning to this 3-bed, 1.5-bath lower duplex house featuring a fully equipped kitchen, bright living space, classic creaky wood floors, comfy accommodations for 6. There's a variety of things to do in MKE including award winning dining, pro Sports, Brewery tours, music festivals and more! Indoors or outdoors, the fun is endless!

6–13 Dec

$396 NZD per night

Guest favourite

Townhouse in Shorewood

4.85 out of 5 average rating, 106 reviews

Gorgeous Shorewood stay by the Lake - Entire Flat

"This sunny 3bd lower flat is large enough to fit your whole family for your trip to Milwaukee. The bathroom is freshly renovated. We have been so lucky to meet the wonderful families and friends who have gathered here and called this space their home away from home. Walking distance to Village of Shorewood, UWM and Lake Michigan, and a short ride to the airport, Summerfest grounds, Harley Museum, the new Fiserv Forum, bars/restaurants/shopping, and much more. Baby friendly with Pack-and-play."

8–15 Sep

$347 NZD per night

Guest favourite

Guest suite in Brookfield

4.99 out of 5 average rating, 182 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax "in the Canopy" of beautiful maples! We’re a Superhosted, verified Guest Favorite, available for the GOP Convention! A comfortable retreat in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer. Perfect location for quick access to the city, or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

2–9 Oct

$280 NZD per night

Guest favourite

Guest suite in Milwaukee

4.98 out of 5 average rating, 167 reviews

THE JUNGALOW- a Milwaukee Craftsman Treasure!

Welcome to our 1924 Craftsman Bungalow! Marrying Prairie House style with the innovations of the Chicago Craftsman, our brick bungalow is awaiting your stay. You'll enjoy the upper suite, with private entrance, two bedrooms, kitchen, and full bath. Newly redone porcelain marbled floors inspire luxury with each step, along with the new 'Article' sectional, 50" TV with streaming, 100% Cotton bedding and towels, a kitchen full of perks and appliances, and lush greenery to keep the air clean.

5–12 Aug

$376 NZD per night

Guest favourite

Home in Wauwatosa

4.98 out of 5 average rating, 177 reviews

Wauwatosa/Milwaukee 10 Minutes from Downtown

Great location near all Milwaukee attractions. Cozy upper two bedroom duplex with keyless entry in quiet Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular bars and restaurants in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital of WI. Near Am Fam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee. COME STAY WITH US!

12–19 Sep

$335 NZD per night

Superhost

Home in Whitefish Bay

4.88 out of 5 average rating, 17 reviews

The Lydell by the Lake

Enjoy this quiet and relaxing getaway in the safe neighborhood of Whitefish Bay. The Lydell House is the perfect family-friendly stay with amazing walkability to nearby Lake Michigan and the Bayshore Mall, or Shorewood business district. You are just a few minutes away from Downtown Milwaukee. Make yourself at home with the use of the fully renovated kitchen, 4 bedrooms, 2 bathrooms, and 2 separate living spaces. A private backyard with seating and a fire pit to enjoy — book now.

3–10 Oct

$635 NZD per night

Guest favourite

Condo in Shorewood

4.93 out of 5 average rating, 261 reviews

English Tudor - Upper Flat blocks from the beach

Sophisticated 100 Yr Old English Tudor Upper Flat with hardwood floors, crown moldings, sunken living room, natural fireplace, built-in bookcases, and fully furnished. Spacious 2200 sq. foot 2nd-floor unit. Safe and QUIET neighborhood just blocks from Atwater beach. Cats are on the property and do not go any guest space. Make sure you have the correct number of guests on your reservation request. Bookings on a Friday or Saturday are required to include both nights.

17–24 Mar

$426 NZD per night

Guest favourite

Apartment in Milwaukee

4.92 out of 5 average rating, 151 reviews

Newport House -Walk to UWM- vintage upper+garage

Enjoy this bright upper flat in the treelined Cambridge Woods neighborhood, on Milwaukee's colorful Eastside. Freshly painted and furnished, sleeps 4, with secure garage and 2nd floor deck. 3 blocks to UWM campus, 2 blocks to city bus lines, close to the Milwaukee River, Oak Leaf Trail bike path, and convenient to restaurants, pubs and shops. Magnificent Lake Michigan with its everchanging beauty is nearby. Newport House is smoke free.

4–11 Jun

$219 NZD per night

Guest favourite

Home in Milwaukee

4.98 out of 5 average rating, 191 reviews

Sunny Upper Flat in Shorewood Near UWM & Downtown

Beautiful two bedroom upper flat in Shorewood with great light. New carpet, pillow top mattresses, coffee brewer, and many more amenities. 5 minutes from UWM and close to lakefront, downtown, I43 and much more. A short ride to Summerfest grounds. Close to many restaurants of many different styles. You will feel at home in our cozy two bedroom flat.

30 Sep – 7 Oct

$195 NZD per night

Guest favourite

Home in Milwaukee

4.98 out of 5 average rating, 189 reviews

Brew City Hideaway - Historic Brewers Hill

Built of Cream City brick in 1858, this is truly one of the oldest standing houses in Milwaukee. It’s just one block north of the original Schlitz Brewery and about .8 miles from the Fiserv Forum! The home also has a fenced in yard with a stamped concrete patio which is shared with the other unit on the property. Also, one off-street parking spot.

26 Dec – 2 Jan

$344 NZD per night

Guest favourite

Home in Whitefish Bay

4.98 out of 5 average rating, 100 reviews

3 BDR Home - World Champion Bucks, Site of the RNC

3 bedroom, sleeps 6, 1.5 bath, full kitchen, newly added laundry washer/dryer, dining room, family living area with gas fireplace. You are minutes away from downtown Milwaukee. Walking distance to the scenic shores of Lake Michigan, Whitefish Bay or Shorewood business district. It is fully furnished to enjoy your home away from home.

20–27 Nov

$446 NZD per night

Guest favourite

Home in Milwaukee

4.99 out of 5 average rating, 121 reviews

Artfully Designed & Cozy Close to Eats & Shopping

Enjoy a stylish experience at the Collected Casa, located 15 minutes west of downtown Milwaukee. The space is filled with an abundance of natural light. Get cozy in this spacious two-bedroom, one-bath home while enjoying everything Milwaukee has to offer.

9–16 Dec

$367 NZD per night