Holiday houses in Whitefish Bay

4.91 out of 5 average rating, 90 reviews

Apartment in Shorewood

Charming home w/ fire pit, walk to Lake Michigan

Welcome to our home in a quiet neighborhood, a short walk to gorgeous views over Lake Michigan and two blocks to restaurants, shopping, and nightlife. Gather around the fire pit and grill dinner in the back patio. Listen to our vinyl collection or stream your own music while playing board games next to the smart TV. Super-fast internet, a fully equipped kitchen with coffee & tea, and in-unit laundry. Two comfy queen beds + a sleeper sofa. Here with kids? We have toys, a Pack n' Play, & more.

4.84 out of 5 average rating, 138 reviews

Townhouse in Shorewood

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."

4.9 out of 5 average rating, 147 reviews

Home in Shorewood

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!

4.97 out of 5 average rating, 118 reviews

Home in Mequon

Historic cottage with fireplace. Pets Welcome!

Step back in time and immerse yourself in the charm of our historic 3-bedroom cottage, part of the renowned Jahn Farmstead, proudly listed on the National Register of Historic Places. Built in the mid-19th century, this Greek Revival-style farmhouse offers a unique blend of historical elegance and modern comfort, ensuring a relaxing and memorable stay. Located 2 miles from the Mequon Public Market and 5 miles from Cedarburg. Pets are welcome and we have acres of land for you to explore!

5 out of 5 average rating, 23 reviews

Apartment in Shorewood

Shorewood's Sunny Craftsman

Welcome to our beautiful, sun-filled, 2-bedroom flat in the amazing lakeshore community of Shorewood! Fully updated in 2023, this lower duplex unit is on a quiet block, and just two blocks from all the wonderful shops, restaurants, and bars on Oakland Ave. Shorewood is very walkable community, with parks, green spaces, beaches, and beer gardens within walking distance. Take advantage of the fully-stocked kitchen with stainless appliances, including dishwasher. Come visit us today!

4.9 out of 5 average rating, 21 reviews

Home in Whitefish Bay

Whitefish Bay Getaway; steps from Starbucks!

Stay in our beautiful, fully-equipped, family-friendly home in the heart of upscale Whitefish Bay! Coffee shops, restaurants, grocery stores, and local shopping just outside your front door. Within five blocks you'll find Lake Michigan, Bayshore Mall, and 5 different playgrounds. Located 7 miles from downtown Milwaukee, access the city easily via highway, Uber, direct bus line, or the picturesque Oakleaf bike trail. Freshly furnished, including new mattresses and linens.

4.95 out of 5 average rating, 109 reviews

Home in Shorewood

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

5 out of 5 average rating, 106 reviews

Home in Milwaukee

Bright Eastside MKE cottage w/ FREE Parking

Welcome to our peaceful little cottage in the heart of Milwaukee. This adorable 2 bedroom, 1 bathroom home will meet all of your needs with 1 king bed, 1 queen bed, a fully stocked kitchen, wifi, driveway for off street parking, and bikes to use on the nearby Oak Leaf Trail. This is the perfect place to enjoy the friendly city of Milwaukee with a comfortable place to sleep at the end of the day. Enjoy all of the restaurants and shops on the Eastside of Milwaukee.

5 out of 5 average rating, 4 reviews

Home in Whitefish Bay

Whitefish Bay Beauty!

In the absolute center of Whitefish Bay -- walk to the library, toy store (Winkies), Stone Creek Coffee, Sendik's grocery store, and Lake Michigan from this 100 year-old charmer. 1st floor has a beautiful living room with a natural fireplace, TV room with cloud couch, and a gourmet kitchen. Stunning outside space with BBQ and fire pit. 2nd floor has 3 bedrooms, office, plus 3 full baths. Awesome shopping, restaurants, and beaches nearby.

4.85 out of 5 average rating, 109 reviews

Home in Shorewood

Modern, Comfortable and Updated in Shorewood!

Walking distance to bars, restaurants, coffee shops, parks and best of all... Lake Michigan! Extensive contemporary remodel with comfortable furniture and plush beds. If you'll need to get some work done we have a large desk and fast WIFI. Laundry is available for your use, located in the basement of home. Free & convenient street parking available in front of the home, always available!

4.99 out of 5 average rating, 239 reviews

Home in Milwaukee

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.

4.9 out of 5 average rating, 150 reviews

Apartment in Riverwest

Cozy Garden Apartment in Eclectic Riverwest

Stay in this cozy studio garden apartment located in the eclectic Riverwest neighborhood! Located within a block of neighborhood staples like Art Bar and Café Corazon and a quick 10 minute drive to downtown, this is the perfect spot for any visit to the Good Land! Ample street parking is available.

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Other great holiday rentals in Whitefish Bay

Private room in Milwaukee

4.82 out of 5 average rating, 499 reviews

Cozy spacious basement w/private entry & bathroom

MicahRating, 5 stars2 weeks ago

Just needed a spot to clean up and sleep and it met my needs at an affordable price.

5 out of 5 average rating, 12 reviews

Apartment in Shorewood

The Little Blue Bungelow

MicheleRating, 5 stars6 days ago

Pam was a delightful host at her charming Little Blue Bungalow. My first impression was how clean it was with a nice window breeze and beautiful decor. The bed was super comfy and supplies needed were provided. A beautiful garden in the back was the perfect place to sip coffee or wine. The neighborhood is charming with welcoming sidewalks and an easy walk to great restaurants and to the lake. I'll definitely be staying there next time I'm in Milwaukee.

Home in Glendale

4.75 out of 5 average rating, 20 reviews

Kletzsch Park Cottage: Glendale (Milwaukee)

KimRating, 5 stars2 months ago

Katie was so responsive. I texted and asked if there would be a blow dryer. She said it would be there when I got there. When I arrived there was a brand new blow dryer. I called that responsive!

Home in Whitefish Bay

5 out of 5 average rating, 3 reviews

Robin's Bluff

GeralynRating, 5 stars7 months ago

My husband and I enjoyed a few days here to relax before the busy holiday season. The entire home was decorated beautifully and I liked the bird theme within much of the decor. King bed was quite comfy. A huge chair in the master was the best. Loved it! Game room was fun and cozy in the evening, with the electic fireplace. We forgot our slippers although it was suggested to bring a pair. So I was thankful for the complimentary slipper socks. Our first evening, we got takeout at Potbelly's in Bayshore Mall, which, to our surprise, had the courtyard decorated already for the holodays. We were happy with our choices for dinner restaurants and coffee shops as well. We also went to Shorewood Nature Preserve and spent some time hiking in the woods and on the beach. Also went to North Point Lighthouse. This home is lovely and I would consider it also for a ladies getaway weekend.

Guest suite in Glendale

4.87 out of 5 average rating, 171 reviews

Private apartment overlooking the river

CoryRating, 5 stars2 months ago

I've stayed in a fair amount of homes in the Milwaukee area over the past 20 years. The location of this place is awesome! The neighborhood is clean and welcoming. Highly Recommend this place!