Upper East Side holiday rentals

We found 45 holiday rentals — enter your dates for availability
Discover a selection of 11 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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    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

When is the best time to visit Upper East Side for a holiday rental?
The best time to visit the Upper East Side for a holiday rental is during the peak season from May to July, with July being the most popular month. This period is superb for travellers seeking vibrant outdoor activities, as the warmer weather invites exploration of the area's beautiful parks and picturesque streets.With temperatures typically ranging from 15 to 30 degrees Celsius, visitors can enjoy everything from leisurely strolls along the waterfront to picnics in local parks. The lively option during these months is enhanced by various community events and festivals, making it an ideal time for those looking to immerse themselves in the local culture.For those considering a more budget-friendly option, December offers a quieter experience with its own charm. The holiday season brings festive decorations and a cosy ambience, superb for a peaceful getaway. Visitors can enjoy the beautiful winter scenery, along with warm drinks at local cafes.Ultimately, the best time to book a holiday rental on the Upper East Side will depend on your preference for vibrant summer activities or a serene winter retreat.
What are the top attractions in Upper East Side, Wisconsin, United States of America?
In Upper East Side, Wisconsin, visitors can explore a variety of attractions that highlight the area's charm. The nearby Milwaukee Art Museum is a significant draw, known for its stunning architecture and diverse art collections. Just a short distance away, the scenic Lake Michigan waterfront offers beautiful views and opportunities for leisurely strolls along the shoreline.In the neighbourhood itself, the historic architecture and tree-lined streets provide a pleasant backdrop for exploring local shops and restaurants. Additionally, the vibrant cultural scene in Milwaukee is easily accessible, with venues like the Pabst Theatre and various galleries showcasing local artists.
Are all fees included in the Upper East Side holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Upper East Side holiday homes with parking?
Stayz offers a wide selection of holiday homes in Upper East Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Upper East Side holiday homes?
You can find great discounts on holiday homes in Upper East Side on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Upper East Side holiday home booking on Stayz?
To find Upper East Side holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Upper East Side?
A long-stay holiday home in Upper East Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Upper East Side holiday home?
Book your Upper East Side holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Upper East Side?
Prices for holiday homes in Upper East Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Upper East Side to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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