Holiday houses in Whitefish Bay

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Top-rated holiday rentals in Whitefish Bay

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Guest favourite

Townhouse in Shorewood

4.85 out of 5 average rating, 136 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."

Guest favourite

Home in Milwaukee

4.89 out of 5 average rating, 128 reviews

Good Land Home - 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 upper duplex house featuring a fully equipped kitchen, bright living space, and comfortable accommodations for 6. There's a variety of things to do in Milw including award winning dining, pro Sports, Brewery tours, endless music festivals and more! Indoors or outdoors, the opportunities are endless!

Top Guest favourite

Home in Mequon

4.97 out of 5 average rating, 118 reviews

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!

Top Guest favourite

Apartment in Shorewood

5 out of 5 average rating, 23 reviews

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!

Top Guest favourite

Home in Whitefish Bay

4.9 out of 5 average rating, 21 reviews

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.

Top Guest favourite

Home in Shorewood

4.95 out of 5 average rating, 108 reviews

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.

Top Guest favourite

Home in Milwaukee

5 out of 5 average rating, 106 reviews

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.

Superhost

Home in Whitefish Bay

5 out of 5 average rating, 4 reviews

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.

Superhost

Home in Shorewood

4.85 out of 5 average rating, 108 reviews

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!

Top Guest favourite

Home in Milwaukee

4.99 out of 5 average rating, 235 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.

Guest favourite

Townhouse in Riverwest

4.92 out of 5 average rating, 245 reviews

Amazing view, Modern Space

Soak your cares away in a luxurious 7-person hot tub while taking in breathtaking panoramic views of the Milwaukee skyline! This chic two-level condo, nestled on a hill above the Milwaukee River, puts you just a 10-15 minute stroll away from the vibrant energy of North Ave, Brady St, and downtown—where the action is always happening.

Guest favourite

Apartment in Riverwest

4.9 out of 5 average rating, 150 reviews

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

Top Guest favourite

Private room in Riverwest

4.96 out of 5 average rating, 643 reviews

Bremen Street House | Private Room

MarthaRating, 5 stars3 days ago

Loved staying here. Communication was great. Everything was clean, organized and a relaxing space. It was nice to soak in the cute bath tub after a long day of exploring. I'd love to stay here again and would recommend.

Superhost

Private room in Milwaukee

4.82 out of 5 average rating, 496 reviews

Cozy spacious basement w/private entry & bathroom

ThomasRating, 5 stars2 weeks ago

Jennifer's place was excellent. The concise yet very clear & easy-to-follow instructions made check-in and check-out a breeze. It was a nice place. I liked that the TV had already some recorded shows on it. Pretty close to downtown Milwaukee. I couldn't have asked for more. I certainly would stay again. 10/10

Guest favourite

Apartment in Milwaukee

4.92 out of 5 average rating, 228 reviews

Chic Apartment with Parking and Gym

CynthiaRating, 5 stars6 days ago

I’ve stayed with Flexhome listings several times during my visits to Milwaukee, and they consistently impress me. Their spaces are not only beautifully designed but also thoughtfully equipped with everything you need for a comfortable stay. The locations are unbeatable—close to everything while still feeling peaceful and private. The building itself is modern and secure, with top-notch amenities that truly elevate the experience. Flexhome continues to set the standard, and I’m already looking forward to booking with them again on my next trip!

Top Guest favourite

Apartment in Shorewood

5 out of 5 average rating, 12 reviews

The Little Blue Bungelow

MicheleRating, 5 stars3 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 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.

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 Racine

4.83 out of 5 average rating, 6 reviews

Lake Michigan Romantic Getaway

MeganRating, 5 stars2 weeks ago

This house really delivered. Being lakeside was such a treat and the floor to ceiling windows overlooking the garden and lake created a wow factor every time we walked into the living area. It was well furnished and equipped with all the kitchen amenities you want in a private home. Loved it.