Photo by Elizabeth Baumann

Bayside holiday rentals

We found 488 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Bayside to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and Wi-Fi. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Bayside

Showing deals for:8 Jan - 15 Jan

Neighborhood coffee roaster 4 blocks away. Try an award-winning Nitro cold brew.
Dining room has decorative fireplace, bar cart, and a variety of drinkware.
One of two bedrooms on main level, with two twin XL beds and closet.
Front living room seating with view to front yard.
Exceptional
(45 reviews)

Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side

Milwaukee

12% off
AU$8,112
for 7 nights, 1 home
AU$1,159 per night
includes taxes & fees
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Dining
Outdoor dining
Living area
Exterior
Exceptional
(6 reviews)

Skyline House on the Hill - Downtown Milwaukee

Milwaukee

8% off
AU$9,390
for 7 nights, 1 home
AU$1,341 per night
includes taxes & fees
Skyline House on the Hill - Downtown Milwaukee
Living area
Private kitchen
Interior
Room
Exceptional
(24 reviews)

Cottage near Mt. Mary College

Milwaukee

7% off
AU$2,263
for 7 nights, 1 cottage
AU$323 per night
includes taxes & fees
Cottage near Mt. Mary College
Room
Terrace/patio
Living area
Private kitchen
Exceptional
(17 reviews)

Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side

Milwaukee

7% off
AU$3,571
for 7 nights, 1 home
AU$510 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side
Living Room with 75" Google TV, Queen Size couch pull out bed.
Estabrook park
Bedroom-3. King size bed and 3rd floor balcony.
Room
Exceptional
(28 reviews)

4 Minutes Walk to Lake Michigan Atwater Park Beach Balconies Family Pet Friendly

Milwaukee

8% off
AU$3,163
for 7 nights, 1 home
AU$452 per night
includes taxes & fees
4 Minutes Walk to Lake Michigan Atwater Park Beach Balconies Family Pet Friendly
Dining
Terrace/patio
Room
Private kitchen
Exceptional
(8 reviews)

Brady St Retreat! 4BR House w Patio & Fenced Yard

Milwaukee

5% off
AU$2,617
for 7 nights, 1 home
AU$374 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Dining
Exterior
Outdoor spa tub
Living area
Exceptional
(34 reviews)

The Gem of Brewers Hill with hot tub and seasonal pool

Milwaukee

7% off
AU$2,854
for 7 nights, 1 home
AU$408 per night
includes taxes & fees
The Gem of Brewers Hill with hot tub and seasonal pool
Roku T.V. in Living Room.
House in Fall/Winter.
Stairs leading to Master Bedroom and Bedroom Two.
Master Bedroom with Ensuite Bath.
Exceptional
(19 reviews)

Whitefish Bay 3Bedroom Entire House Sleeps 4

Milwaukee

25% off
AU$2,238
for 7 nights, 1 home
AU$320 per night
includes taxes & fees
Whitefish Bay 3Bedroom Entire House Sleeps 4
Beautiful refinished hardwood floors throughout the house; stair mats available.
3-BR house exclusively for your enjoyment.
DR into kitchen
Enjoy morning coffee and/or happy hour.
Exceptional
(9 reviews)

3BR house. East Side very near lake, beach, shops; central AC; driveway parking!

Milwaukee

11% off
AU$5,239
for 7 nights, 1 home
AU$748 per night
includes taxes & fees
3BR house. East Side very near lake, beach, shops; central AC; driveway parking!
Room
Outdoor dining
Private kitchen
Interior
Exceptional
(12 reviews)

Gorgeous space with huge porch.

Milwaukee

7% off
AU$2,297
for 7 nights, 1 home
AU$328 per night
includes taxes & fees
Gorgeous space with huge porch.
Lobby
Interior
Interior
Private kitchen
Exceptional
(18 reviews)

Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking

Milwaukee

7% off
AU$2,864
for 7 nights, 1 apartment
AU$409 per night
includes taxes & fees
Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking
Interior
Private kitchen
Room
Living area
Exceptional
(13 reviews)

The Washington Suite on the main street in Downtown Cedarburg

Cedarburg

7% off
AU$1,748
for 7 nights, 1 apartment
AU$250 per night
includes taxes & fees
The Washington Suite on the main street in Downtown Cedarburg

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the natural setting in Bayside

The parks and beaches provide a pleasant backdrop to your holiday home in Bayside. One of the city's many top draws is its restaurants. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Bayside

Are you looking for attractions to visit while you're in the area? Venture out of your holiday home and check out everything that Bayside has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ray's MTB Indoor Mountain Bike Park (5.3 mi / 8.5 km)
  • Cedar Creek Winery (9.5 mi / 15.2 km)
  • Henry W. Maier Festival Park (10.4 mi / 16.7 km)
  • Milwaukee Mile Speedway (12.3 mi / 19.9 km)
  • Milwaukee County Zoo (12.5 mi / 20.1 km)
  • Port Washington Ghost Walk (14.5 mi / 23.3 km)

Exploring the natural features in Bayside

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Bayside is a great place to get outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Veteran's Park (9.5 mi / 15.3 km)
  • Mitchell Park Horticultural Conservatory (10.9 mi / 17.6 km)
  • Boerner Botanical Gardens (18.1 mi / 29.1 km)
  • Atwater Park & Beach (6.4 mi / 10.3 km)
  • Lake Park (7.9 mi / 12.6 km)
  • Bradford Beach (8.3 mi / 13.4 km)

Transport to and around Bayside

Fly into Milwaukee, WI (MKE-General Mitchell Intl.), the closest airport, located 16 mi (25.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Waukesha, WI (UES-Waukesha County), which is 19.7 mi (31.7 km) away.

Frequently asked questions

What is the best area to stay in Bayside when booking a holiday rental?
When considering a holiday rental in Bayside, Wisconsin, the best area to stay is the picturesque neighbourhood near Lake Michigan. This charming locale is known for its serene atmosphere and beautiful natural surroundings, making it an ideal spot for a relaxing getaway.One of the highlights of staying in this area is the proximity to the stunning Schlitz Audubon Nature Centre, where you can enjoy miles of walking trails and observe a variety of wildlife in their natural habitat. Additionally, the nearby Lake Park offers lovely picnic spots and scenic views of the lake, superb for leisurely afternoons.In terms of holiday rentals, there are a diverse range of properties available, suiting different preferences and group sizes. Staying in this neighbourhood not only provides easy access to these attractions but also offers a peaceful retreat after a day of exploration.
When is the best time to visit Bayside for a holiday rental?
The peak time to visit Bayside is from May to July, attracting holidaymakers looking for a charming getaway along the scenic shores of Lake Michigan. During these months, the area comes alive with outdoor activities, superb for those who appreciate a variety of experiences, from leisurely lakefront strolls to engaging in water sports.July is particularly popular, offering warm temperatures averaging around 25 to 30 degrees Celsius, making it ideal for picnics in the park, beach days, and enjoying local festivals. This vibrant setting is complemented by the opportunity to explore nearby attractions, such as the stunning Schlitz Audubon Nature Centre, which provides a superb blend of relaxation and adventure.For those considering a budget-friendly option, November presents a unique time to visit. During this time, the crisp autumn air offers a different kind of charm, with opportunities for peaceful walks and the chance to witness the stunning transformation of the landscape as the leaves change colour.Ultimately, your ideal time in Bayside will depend on whether you prefer the lively summer buzz or the tranquil beauty of late autumn.
What are the top attractions in Bayside?
In Bayside, Wisconsin, visitors can enjoy a serene suburban atmosphere with access to several attractions. The community is known for its beautiful parks, such as the scenic Bayside Park, which features walking trails, picnic areas, and a playground, making it ideal for families and outdoor enthusiasts. Nearby, the stunning Lake Michigan shoreline offers opportunities for walking and enjoying nature, with several access points for lakeside activities.For those interested in shopping and dining, the nearby Village of Shorewood has a variety of local shops and restaurants to explore. Additionally, the nearby Schlitz Audubon Nature Centre provides a fantastic opportunity for wildlife observation and educational programs, located in a natural setting with trails and exhibits.Cultural attractions can be found just a short drive away in Milwaukee, where visitors can explore the Milwaukee Art Museum, the Harley-Davidson Museum, and the vibrant Historic Third Ward, which is known for its galleries and eateries.
Are all fees included in the Bayside 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 Bayside holiday homes with parking?
Stayz offers a wide selection of holiday homes in Bayside 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 Bayside holiday homes?
You can find great discounts on holiday homes in Bayside 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 Bayside holiday home booking on Stayz?
To find Bayside 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 Bayside?
A long-stay holiday home in Bayside 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 Bayside holiday home?
Book your Bayside 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 Bayside?
Prices for holiday homes in Bayside 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 Bayside 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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