Upper East Side holiday rentals

We found 43 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Upper East Side that are perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a fireplace. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
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Why visit Upper East Side

  • Urban parks and outdoor spaces: Enjoy scenic green spaces perfect for leisurely strolls and family picnics.
  • Cultural attractions: Discover local art museums and cultural venues reflecting the neighbourhood's artistic flair.
  • Beach areas: Relish sunny, family-friendly beach spots ideal for water-based fun.
  • Vibrant cityscape: Experience a lively urban environment with bustling streets and local charm.
  • Modern yet local: Embrace a blend of contemporary city life with warm, inviting neighbourhood character.

Popular types of accommodation around Upper East Side

Discover Upper East Side, Milwaukee, Wisconsin - a charming neighbourhood offering a variety of holiday homes, apartments, and condos. Here, you can explore Upper East Side holiday rentals, find Upper East Side Milwaukee homes, and enjoy nearby accommodations that suit every traveller's needs. With local attractions and unique experiences, this area promises a memorable stay for families, couples, and solo adventurers alike.

  • Private Holiday Homes: These exclusive dwellings offer a premium retreat for those seeking a private and luxurious escape in Upper East Side.
  • Apartments: Modern and comfortable, apartments provide a convenient base for exploring all that Upper East Side has to offer.
  • Condos: Stylish condo options blend contemporary living with ease of access to local attractions in Upper East Side.
  • Cabins: Ideal for nature enthusiasts, cabins in Upper East Side offer a cosy, rustic experience away from the bustle.
  • Cottages: Quaint cottages provide a charming and intimate setting for a memorable Upper East Side getaway.**

Top attractions near Upper East Side

The Upper East Side in Milwaukee, Wisconsin, offers a delightful mix of urban parks, art museums, and beach areas, making it an ideal destination for outdoor enthusiasts and families alike. Visitors can immerse themselves in cultural experiences while enjoying the scenic beauty of the neighbourhood. The area is perfect for those seeking a vibrant city atmosphere, with plenty of attractions and activities to explore for all ages.

  • Milwaukee Art Museum: A stunning architectural marvel that houses an impressive collection of art, offering a vibrant cultural experience with its diverse exhibitions and breathtaking lakefront views.
  • Lakeshore State Park: An urban oasis perfect for families, featuring walking trails, picnic areas, and scenic vistas of Lake Michigan, ideal for outdoor enthusiasts and relaxation alike.
  • Pebble Beach: A charming beach spot with soft pebbles and tranquil waters, perfect for sunbathing, leisurely strolls, and enjoying the serene lakeside atmosphere.

Things to do recommended for couples

For a romantic adventure near Upper East Side, consider the Sky Safari cable car gondola, located 14km away. Enjoy breathtaking views while embracing the outdoors, perfect for couples seeking a thrilling yet intimate experience in Milwaukee.

Things to do recommended for families

Families will delight in the Milwaukee Public Museum, where they can explore interactive exhibits, or enjoy the scenic beauty of Lake Park, perfect for picnics and strolls. The nearby Milwaukee County Zoo offers a fantastic day out with a variety of animals and engaging activities for children.

Things to do recommended for groups

Groups visiting the Upper East Side in Milwaukee can experience the thrill of motor racing at Milwaukee Mile Speedway, just 13km away, or embark on an adventurous zipline course at Sky Trail, located 14km away, perfect for outdoor enthusiasts.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Upper East Side

If you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to apply the appropriate filters based on your key priorities. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Upper East Side with a group: Consider the number of bedrooms required, along with features like a fully equipped kitchen or an outdoor area for group gatherings. Fortunately, you can apply filters for all these options and more on Stayz.
  • Traveling to Upper East Side with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring suitable facilities, such as a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Upper East Side: For many, a family holiday feels incomplete without their beloved four-legged companion. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Upper East Side: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect destination. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Upper East Side

Discover the charm of Upper East Side, Milwaukee, where family-friendly streets meet a vibrant urban vibe. Enjoy delightful cityscapes, local parks, and a bustling atmosphere that captures both business and romantic appeal. The neighbourhood offers a sunny, trendy setting perfect for outdoor adventures and cultural explorations, right in the heart of Milwaukee. This is an ideal destination for those seeking a blend of modernity and warm, local character.

  • Milwaukee: Milwaukee is a vibrant metropolis located along the shores of Lake Michigan. As the city that envelops the Upper East Side, it offers a diverse range of experiences for visitors, from outdoor adventures to romantic outings. The city is known for its lively music scene, theatres, and educational venues. Key attractions include the impressive sports facilities and event venues that host various activities throughout the year. Whether you’re exploring the scenic lakeside parks or enjoying a concert, Milwaukee has something for everyone.
  • Downtown Milwaukee: Situated approximately 3km from Upper East Side, Downtown Milwaukee is a bustling neighbourhood that serves as the city’s core. It is ideal for families and business travellers alike, offering a rich urban experience. Visitors can enjoy a variety of cultural activities, including music concerts and theatrical performances. Key landmarks include the modern convention centre and expansive event spaces, making it a hub for both leisure and business events. The vibrant atmosphere ensures there’s always something happening, from festivals to art exhibitions.
  • Brewers Hill: Located about 3km from Upper East Side, Brewers Hill is a charming neighbourhood that blends family-friendly activities with a sporty vibe. It is known for its community spirit and access to various venues for theatre and music events. The area features picturesque streets and is in close proximity to sports facilities, making it an excellent spot for both relaxation and recreation. Whether you’re cheering for a local team or enjoying a community festival, Brewers Hill offers a delightful experience for all ages.

Booking with Stayz is simple

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can often lead to better prices. Moreover, extending your stay can result in significant savings. To discover the ideal Stayz property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board provides a dedicated area where you can craft new journeys, resume your plans, or review and organise your current bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Upper East Side?
Houses are the most popular style of holiday home in Upper East Side, according to our data. Even if you've got a different idea about what you want, Stayz has holiday homes in a variety of sizes and shapes. Browse our many options to find your perfect match.
How much does it cost to rent a holiday home in Upper East Side?
Property type, length of stay and season are among the factors that can determine the price of a holiday home. Simply enter your travel dates to find the ultimate escape. From cosy country cottages to expansive luxury villas, all Stayz holiday homes provide incredible value.
How much does it cost to rent a beach house in Upper East Side?
Prices for beach houses in Upper East Side differ depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Stayz and how many guests to view your options and prices. From there you can use our filter tool to refine your search by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday homes in Upper East Side?
Yes. You'll have a choice of four holiday homes that allow pets in Upper East Side. Lots of our pet-friendly holiday homes even come with space outdoors for your four-legged pal to play around in, complimentary treats, special dog beds and proximity to parks and green space. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Stayz.
What are popular home amenities in Upper East Side?
A lake view, a chef and an electric car charging station are rated the most popular home amenities in Upper East Side. Whether you're travelling on your own, with your spouse or a group of friends, Stayz will help you find a holiday home that suits your tastes with all the features you need.
Are there large group holiday homes in Upper East Side?
With two holiday homes that can host 10 or more guests in Upper East Side, you won't have to cross anyone off the invite list. From family holidays to special events like birthday parties and weddings, Stayz will help you find a large group home to match the occasion.
Are there holiday homes in Upper East Side that welcome kids?
With four family-friendly holiday homes to choose from in Upper East Side, now is a great time to introduce the kiddos to the pleasures of travel. Just check our "Properties good for families" filter box to view stays packed with conveniences perfect for holidaying families, like multiple bedrooms, pools, entertainment areas and bunk beds.
What are the top attractions for families in Upper East Side?
There are loads of awesome things to do and see with the family in Upper East Side, such as:

  • Harley-Davidson Museum
  • Milwaukee County Zoo
  • Milwaukee Public Museum

Are there holiday homes with WiFi in Upper East Side?
Upper East Side has two holiday homes with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Stayz homes make it easy to go online.
How can I find holiday homes with air conditioning in Upper East Side?
You'll find four Stayz holiday homes with air conditioning in Upper East Side giving you that cool, cool breeze and extra element of comfort. Simply enter your desired travel dates and then take advantage of our filters to help you locate properties with air conditioning.
How old do you have to be to rent a holiday home in Upper East Side?
The minimum age permitted can differ across properties on Stayz, so be sure to check the rules of the holiday home in Upper East Side you're considering. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Upper East Side for?
It all depends on the Upper East Side property. To browse available options offering extended stays, just type your dates and number of guests into the Stayz search page. You can look forward to having the entire place to yourself, along with the comforts of home like a fully-equipped kitchen, air conditioning and outdoor spaces where the little ones can play. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.