Fifth Ward holiday rentals
We found 112 holiday rentals — enter your dates for availability
Discover a selection of 18 homes, 22 apartments and other holiday rentals in Fifth Ward that are perfect for your trip. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a fireplace. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - Fifth Ward

Downtown View Luxury Near Lake Michigan
Sleeps 3 · 1 bedroom · 1 bathroom

Studio View Of Downtown Near Lake Michigan
Sleeps 3 · 1 bedroom · 1 bathroom

The Bentley - Frida's Reign, Heart of Walkers Point w/Garage,Yard
Sleeps 6 · 2 bedrooms · 1 bathroom

Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6
Sleeps 6 · 2 bedrooms · 1 bathroom

Fabulous Walkers Point Mansion w/ Bar andFireplace
Sleeps 10 · 5 bedrooms · 3 bathrooms

3 Premium Loft 2 Queen Beds at The Iron Horse Hotel, Pet-friendly Property!
Sleeps 12 · 3 bedrooms · 3 bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
When is the best time to visit Fifth Ward for a holiday rental?
The best time to visit Fifth Ward for a holiday rental is during the peak season from May to July, with July being particularly popular. This vibrant period attracts visitors looking to enjoy the warm summer weather and partake in various outdoor activities, from hiking the scenic trails to exploring the local parks. With temperatures often reaching the mid to high 20s Celsius, it's ideal for travellers.In addition to the pleasant climate, this season offers lively local events and activities, making it a fantastic time for socialising and immersing yourself in the community spirit. The abundance of greenery and blooming flowers during these months enhances the beauty of the area, great for those who appreciate nature and want to enjoy outdoor picnics or leisurely strolls.If you're seeking a more budget-friendly option, consider visiting in December. While this is the low season, it provides a unique charm with wintery landscapes and a quieter atmosphere, allowing for peaceful getaways and introspective moments. Think of cosy evenings by the fire and the chance to enjoy the local winter activities without the usual crowds.Ultimately, the choice of when to visit Fifth Ward will depend on whether you prefer the bustling summer vibe filled with activities or the tranquil beauty of winter.
Are all fees included in the Fifth Ward 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 Fifth Ward holiday homes with parking?
Stayz offers a wide selection of holiday homes in Fifth Ward 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 Fifth Ward holiday homes?
You can find great discounts on holiday homes in Fifth Ward 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 Fifth Ward holiday home booking on Stayz?
To find Fifth Ward 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 Fifth Ward?
A long-stay holiday home in Fifth Ward 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 Fifth Ward holiday home?
Book your Fifth Ward 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 Fifth Ward?
Prices for holiday homes in Fifth Ward 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 Fifth Ward 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.
