Holiday houses in Shorewood

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Top-rated holiday rentals in Shorewood

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Superhost

Townhouse in Shorewood

4.84 out of 5 average rating, 139 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, 130 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 Shorewood

4.99 out of 5 average rating, 100 reviews

The Menlo Guesthouse

A vintage, lower flat in a 100-year-old duplex with modern comforts and conveniences. Perfect for short or long stays while visiting Milwaukee. Situated in the walkable/bikeable Milwaukee neighborhood of Shorewood. The flat is located just a few blocks north of UWM and a few blocks east of the Oak Leaf Trail. Three minutes from Atwater Beach. Ten minutes or less to Bradford Beach, museums, and Summer Fest. Fifteen minutes or less to Fiserv Forum, Panther Arena, and American Family Field.

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 Shorewood

4.95 out of 5 average rating, 109 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.

Top Guest favourite

Townhouse in Upper East Side

4.99 out of 5 average rating, 122 reviews

Historic Gem|Steps to UWM|Lake Mich|Free Parking

🔹 5-Star Rated | Superhost Quality | Fast Wi-Fi | Free Parking 🔹 🏡 Experience a Slice of Milwaukee’s History in a 100-Year-Old Home! Step inside this charming first-floor retreat—a beautifully preserved prairie-style home blending historic elegance with modern convenience. Located right across from UWM, this top-rated Airbnb is perfect for visiting students, faculty, families, and travelers looking for a relaxing, walkable neighborhood.

Guest favourite

Apartment in Shorewood

4.87 out of 5 average rating, 93 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.

Superhost

Home in Shorewood

4.85 out of 5 average rating, 110 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, 240 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.

Superhost

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.

Top Guest favourite

Apartment in Riverwest

4.95 out of 5 average rating, 243 reviews

Comfortable Riverwest apartment

Open, modern space in older home. Airbnb is located on the first floor, basic amenities are included. The family lives upstairs with very active kids that can be loud at times. Walking distance to coffee shops and neighborhood businesses, buses, downtown and the Milwaukee river. Street parking.

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Popular amenities for Shorewood holiday rentals

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Other great holiday rentals in Shorewood

Top Guest favourite

Private room in Riverwest

4.96 out of 5 average rating, 645 reviews

Bremen Street House | Private Room

RebeccaRating, 5 stars5 days ago

Perfect for what we needed. Matched the description. Susan was very responsive and accommodating.

Guest favourite

Apartment in Milwaukee

4.92 out of 5 average rating, 230 reviews

Chic Apartment with Parking and Gym

JayRating, 5 stars4 days ago

Felt very safe (unit is in a secure building). Instructions for getting in are clear. Nice place to say and would stay again.

Top Guest favourite

Apartment in Shorewood

5 out of 5 average rating, 13 reviews

The Little Blue Bungelow

MicheleRating, 5 stars1 week 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 Milwaukee

5 out of 5 average rating, 4 reviews

Tranquil Storybook Cottage near UWM

CraigRating, 5 stars1 week ago

Absolutely amazing and the best home-away-from-home experience we’ve ever had. This incredible Ernest Flagg cottage could not have been any more charming. So much love and thought have gone into every nook and cranny—from the delightful decor featuring some delightful artwork to gorgeous plants and flowers—that our party of four felt so completely welcome and comfortable, we were sad to leave. Our only regret was that we didn’t have time to take proper advantage of the amazing LP record collection! But that just means we’ll have to come back for more! ❤️

Bungalow in Shorewood

4.93 out of 5 average rating, 30 reviews

The Hugalow - A Family Friendly Renovated Bungalow

ChristopherRating, 5 stars15 months ago

The Hugalow provided my family and I with the warm embrace that we were looking forward to during our trip. It was located in an extremely charming neighborhood with friendly locals and great coffee shops. The home itself was very colorful and cozy. My children loved their spaces. So did our dog! Christina was very accommodating and we are forever grateful for her efforts.

Guest favourite

Home in Lower East Side

5 out of 5 average rating, 13 reviews

Spacious & Stylish 1 Bedroom

ErinRating, 5 stars3 days ago

Our stay in Milwaukee was fantastic! We arrived late on our check-in day and it was extremely easy to find our parking space and enter the rental (even in the dark!). Leonard's instructions were so thorough and he was very responsive when we did have questions. The cozy space was the perfect "home away from home". The bed was SO comfortable, I don't think I've slept so well on a vacation before! The pristine kitchen had everything we could possibly need and the bathroom was well stocked with all necessary products (even hair tools!). Even though we came in an intense heat waves -- the provided AC cooled the entire space and was such an oasis from the outside. The rental is walking distance to many cute shops, restaurants, and site-seeing locations. We were able to walk all the way downtown with no issue -- the neighborhood was extremely peaceful and safe. We will absolutely be back! Thank you, Leonard!

Home in Shorewood

4.71 out of 5 average rating, 7 reviews

Charming 3* Bedroom Home + Parking

RyanRating, 5 stars10 months ago

Just spent a weekend at this awesome property with the boys, and it couldn’t have been better! The place has everything you need for a relaxed time—comfy beds, a great kitchen for cooking up some meals, and plenty of space to hang out. The location is spot on too—close enough to hit up some local spots but still nice and quiet for when you just want to chill. Definitely coming back next time we need a getaway!

Top Guest favourite