Jackson holiday lettings

We found 45 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Jackson that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as parking and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Jackson

Showing deals for:14 Nov - 21 Nov

Image gallery for Cozy Cedarburg Country-Side House

Private kitchen
9.4 out of 10 rating
Exceptional
(26 reviews)

Cozy Cedarburg Country-Side House

Cedarburg, WI

7% off
Price is £1,233
£176 per night
includes taxes & fees
Cozy Cedarburg Country-Side House

Find spaces that suit your style

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    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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Jackson

Find out more about Jackson

Take in the picturesque beauty of Jackson

Enjoy the festivals and other features of Jackson. This city's cycling, shopping and restaurants attract many visitors, as does its welcoming and walkable location. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Jackson

Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Jackson a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Washington County Fair Grounds (2.2 mi / 3.6 km)
  • Cabela's (3.3 mi / 5.3 km)
  • Little Switzerland (5.6 mi / 9.1 km)
  • Cedar Creek Winery (9 mi / 14.6 km)
  • Holy Hill (9.8 mi / 15.8 km)
  • Harley Davidson Factory (10.2 mi / 16.4 km)

Exploring the natural features in Jackson

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Jackson. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Big Cedar Lake (6.1 mi / 9.8 km)
  • Pewaukee Lake Beach (17.3 mi / 27.8 km)
  • Pewaukee Lake (18.7 mi / 30.1 km)
  • West Bend Labyrinth Garden (7.5 mi / 12.1 km)
  • Regner Park (7.6 mi / 12.2 km)
  • Lynden Sculpture Garden (15.4 mi / 24.8 km)

Transport options to and around Jackson

The nearest airport is in Waukesha, WI (UES-Waukesha County), located 20.1 mi (32.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Milwaukee, WI (MKE-General Mitchell Intl.), which is 29.2 mi (46.9 km) away.

Frequently asked questions

What is the best area to stay in Jackson when booking a holiday rental?
When considering a holiday rental in Jackson, Wisconsin, the area surrounding the scenic Kettle Moraine State Forest is an excellent choice. This region offers a beautiful backdrop of rolling hills and lush woodlands, making it great for nature enthusiasts. You can explore the many hiking and biking trails that weave through the forest, providing ample opportunities for outdoor activities and picturesque views.

Another appealing area is the downtown vicinity, where you can immerse yourself in the local culture. This area boasts a charming small-town atmosphere with quaint shops, cafes, and restaurants that showcase the community's hospitality. Staying here allows you to be within walking distance of delightful eateries and unique boutiques, as well as the local farmers' market, which is a highlight during the warmer months.
How much does it cost to rent a holiday home in Jackson?
Prices for holiday rentals in Jackson 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Jackson to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Jackson holiday house rentals?
You can find great discounts on house rentals in Jackson on Vrbo, 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 find long-stay holiday rentals in Jackson?
A long-stay holiday rental in Jackson 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Jackson holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Jackson 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 on Vrbo 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.
When is the best time to visit Jackson for a holiday rental?
The best time to book a holiday rental in Jackson is during the peak season from June to August, with July being particularly popular among visitors. This vibrant summer period invites travellers to explore the beautiful landscapes and partake in an array of outdoor activities. With average temperatures hovering around 25°C, it's an ideal time for hiking, biking, and enjoying local festivals.

During these months, Jackson comes alive with events, including farmers' markets and outdoor concerts, creating a lively atmosphere that draws tourists eager to experience the charm of the area. The long, sunny days provide ample opportunity for sightseeing and creating lasting memories with family and friends.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a unique opportunity to witness the peaceful transition into winter, with fewer crowds and beautiful autumn scenery still lingering in the landscape. It's a great time for those who appreciate a quieter escape, perhaps enjoying scenic walks or cozy evenings by the fire.
How early should I book a Jackson holiday rental?
Book your Jackson holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Jackson home rental booking on Vrbo?
To find Jackson holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Jackson holiday rental prices shown on Vrbo?
Vrbo 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.

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