Holiday houses in Glendale

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Top-rated holiday rentals in Glendale

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

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Guest favourite

Apartment in Shorewood

4.92 out of 5 average rating, 96 reviews

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.

Top Guest favourite

Home in Thiensville

4.97 out of 5 average rating, 150 reviews

Quaint & Cozy Town Cottage Desirable N. Shore

Adorable small Town Cottage walkable to coffee shops, restaurants, parks & the riverwalk…bring the pup and experience something sweet. Everything you need to get away, business trip or extended stay. Well appointed kitchen, 2 small but cute baths with heated floors(1) and fast WiFi. Urban-like walk-ability w/ small town charm! Walk to (excellent) authentic Himalayan food at the Cheel or a glass of wine at Glaze and paint a new coffee mug! Go out or kick back with the fire/grill and s’mores!

Guest favourite

Apartment in Shorewood

4.95 out of 5 average rating, 111 reviews

Updated, Bright & Modern Space in Shorewood!

Beautiful unit in the top floor of a duplex in the heart of Shorewood! Walking distance to bars, restaurants, coffee shops - and best of all... Lake Michigan! Check out the extensive guide book to really maximize your stay! Plush beds & fully furnished kitchen along with spacious living and dining areas. The large balcony area off the front of the unit makes for the perfect space to privately lounge in the sun! Free & convenient street parking available in front of the home, always available!

Guest favourite

Apartment in Bay View

4.95 out of 5 average rating, 354 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Superhost

Home in Whitefish Bay

4.67 out of 5 average rating, 9 reviews

Amazing Family Home in Whitefish Bay!

Welcome to this recently renovated four-bedroom Tudor home on a beautiful tree-lined street in the heart of Whitefish Bay, just a few blocks from parks, coffee shops, restaurants, and the beach at Lake Michigan. Just a 15-minute drive down scenic Lake Drive to downtown Milwaukee. Features four bedrooms, two full bathrooms and a powder room, with a fully finished basement perfect for kids’ play space or watching the game. Spacious fenced backyard with a patio, grill, and outdoor furniture.

Guest favourite

Home in Glendale

4.93 out of 5 average rating, 29 reviews

Bass & Sparrow - Spa Retreat on the MKE River

Offering my personal peaceful Milwaukee home on the Milwaukee river just minutes from downtown. Wanna get your healing and nature on while visiting Milwaukee? Fish right from the backyard. Have a fire inside or out, hot tub it, enjoy a hot outdoor shower, watch the deer, river otters, mink, beaver, bald eagles, and song birds galore. All this just a $20 Uber ride to downtown for dinner and drinks. And to add to your relaxing escape, you can also book an in house massage!

Guest favourite

Home in Shorewood

4.96 out of 5 average rating, 121 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.

Guest favourite

Home in Lincoln Park

4.88 out of 5 average rating, 92 reviews

Cozy 2-bedroom cottage close to everything!

This newly remodeled, cozy cottage has been called a hidden gem. It’s walking distance from Bayshore Mall. Five minute walk to biking/hiking trail, Milwaukee River for fishing and kayaking and Whitefish Bay. Twelve minutes from Lake Michigan, Downtown and the Historic Third Ward! Booking requirements: Full/Complete Air BnB profile. Government ID check for pre-approval and upon arrival. No parties or events. Active noise monitoring device. No pets allowed.

Guest favourite

Home in Mequon

4.89 out of 5 average rating, 177 reviews

Mequon Ranch Experience

Escape to our stunning vacation home in Mequon, WI for a peaceful group getaway. Completely renovated and fully furnished, our home comfortably accommodates up to 8 guests. Enjoy complete privacy on our one-acre lot, and relax on the patio, grill up a delicious meal, or gather around the fire pit. Only blocks away from the Milwaukee River and minutes to downtown Mequon, our home offers easy access to nearby attractions. Book now for an unforgettable stay!.

Superhost

Home in Glendale

4.78 out of 5 average rating, 132 reviews

Retro Riverside Retreat, Backyard Oasis, Hot Tub

Escape to the retro riverside retreat! This large home sleeps 16+ and offers an incredible outdoor area with a hot tub, fire-pit, and river access. Your outdoor oasis and awaits. Inside, enjoy 6 bedrooms, 3 bathrooms, a huge dining table, and a game room. Perfect for large groups, family gatherings, or a peaceful oasis. Just a short 15-minute drive to vibrant Milwaukee attractions. Experience relaxation and adventure in our remarkable riverside getaway.

Top Guest favourite

Home in Wauwatosa

5 out of 5 average rating, 275 reviews

The Little Gray House

Time to plan your fall and winter getaways! Stay with us and enjoy all the amenities of the Little Gray House including a shed bar with food truck style windows and TV, hot tub, comfortable bedrooms and more! We've also just added a tankless water heater - never run out of hot water! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Guest favourite

Apartment in Shorewood

4.87 out of 5 average rating, 102 reviews

English Tudor -Floor 3 Suite blocks from the beach

Total 4 beds - 2 Queen, 1 twin, 1 full Floor 3 is a private, peaceful, comfortable suite. Newly tiled bathroom and renovations throughout. Comfortably Sleeps 6 beds (2 queen, 1 double, 1 twin. There is 1 full bathroom. I have a cat that goes in the lower level stairway to access their restroom in the basement. But they do not go in the 3-floor unit. I also have 2 lovely dogs you may see when coming in.