Jackson Holiday Rentals

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Holiday Rentals in Jackson

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (104)
"Very nice apartment and right down town location is perfect!"
Kasa Westown Milwaukee

KLVG - Malt House

4.0 star property
9.0 out of 10, Wonderful, (9)
"Loved the uniqueness, location and cleanliness of the unit."
KLVG - Malt House

KB - Prospec

3.0 star property
7.6 out of 10, Good, (7)
"Our stay was great. The property was at it was described and expected. The owner was available via text and communicated with me when I had questions. We would stay again!"
KB - Prospec

Three bedrooms upstairs

9.6 out of 10, Exceptional, (74)
"The property was cute and stylish. I would stay here again. "
The price is NZ$401
includes taxes & fees
13 Oct - 14 Oct
Three bedrooms upstairs

Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking

2.0 star property
9.6 out of 10, Exceptional, (4)
"Parking was great"
The price is NZ$258
includes taxes & fees
27 Oct - 28 Oct
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking

Cozy 2 Bedroom Downtown Milwaukee Apartment

9.8 out of 10, Exceptional, (8)
"Stayed here two nights in June with my husband to attend Summerfest. The unit is walking distance to downtown Milwaukee, about 1.5 miles away from Summerfest (Uber ride was less that 10). Check in process was easy and host was quick to respond to questions. The unit is on the second floor of a house, so keep in mind that you must be able to go up one flight of stairs to enter unit (not wheelchair accessible). Unit had a well stocked kitchen with several cooking utensils, including a coffee maker...
Cozy 2 Bedroom Downtown Milwaukee Apartment

Wooded Hills/Indoor Pool/Hot Tub/Arcade

9.8 out of 10, Exceptional, (49)
"House was clean and spacious. Pool and extra amenities were great!"
Wooded Hills/Indoor Pool/Hot Tub/Arcade

Downtown Eastside gem near Fiserv Forum Water St Brady St

9.2 out of 10, Wonderful, (43)
"Walking distance to several great bars, restaurants, breweries and the summer fest area. We really enjoyed our stay!"
The price is NZ$574
includes taxes & fees
7 Oct - 8 Oct
Downtown Eastside gem near Fiserv Forum Water St Brady St

17-acre Private Oasis estate with, an indoor pool, and private lake, sleeps 16

8.0 out of 10, Very good, (7)
"This house is definitely a unique treasure. We took our Girl Scout troop here to celebrate. The property definitely has something for everyone. We caught and released some big fish down by the pond, and the girls liked catching frogs. The beautiful landscape made a perfect atmosphere for an outdoor fire. The girls loved the bunk bed, game room, tv room, and of course the pool! The girls kept calling it the jungle oasis with all the beautiful plants. "
The price is NZ$3,318
includes taxes & fees
9 Oct - 10 Oct
17-acre Private Oasis estate with, an indoor pool, and private lake, sleeps 16

Quiet House

6.8 out of 10, (5)
"We were mainly at the property to drop our stuff off, enjoy Summerfest, sleep and shower! Property was clean. Had a little trouble with the front door code but were able to get it to work. "
The price is NZ$332
includes taxes & fees
7 Oct - 8 Oct
Quiet House

4 bed house on the shore of Lake Michigan

9.4 out of 10, Exceptional, (61)
"Property was a little worn, but location and setup was fantastic. "
The price is NZ$548
includes taxes & fees
7 Oct - 8 Oct
4 bed house on the shore of Lake Michigan

Studio apt w/ laundry + parking

10.0 out of 10, Exceptional, (25)
"Great place. "
The price is NZ$206
includes taxes & fees
19 Oct - 20 Oct
Studio apt w/ laundry + parking

Stunning Upscale Retreat - Steps From Everything

9.8 out of 10, Exceptional, (31)
"Great location and super clean property. Highly recommend."
The price is NZ$925
includes taxes & fees
13 Oct - 14 Oct
Stunning Upscale Retreat - Steps From Everything

Deer District Studio Apt JC3 - One Block from Fiserv and Baird

10.0 out of 10, Exceptional, (1)
"Straightforward checking in/out process."
The price is NZ$220
includes taxes & fees
7 Oct - 8 Oct
Deer District Studio Apt JC3 - One Block from Fiserv and Baird

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

9.8 out of 10, Exceptional, (25)
"Loved the location "
The price is NZ$486
includes taxes & fees
19 Oct - 20 Oct
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

3-bedroom lake cottage in the Kettle Moraine State Forest

9.8 out of 10, Exceptional, (44)
"Great place to stay the owners were extremely accommodating!"
3-bedroom lake cottage in the Kettle Moraine State Forest

Wonderful craftsman home in Wauwatosa

9.6 out of 10, Exceptional, (51)
"House was great and very clean. Owner was very easy to communicate with and quick to respond. Awesome location and walkable to many spots on North Ave. "
Wonderful craftsman home in Wauwatosa

NEW • Unique Design • Fully Loaded Kitchen

10.0 out of 10, Exceptional, (22)
"We had a great visit to Port Washington. The house was clean and the check in check out process was easy!"
NEW • Unique Design • Fully Loaded Kitchen

Private Home w/ Backyard + Game Table – Walk to Brady St Fun

10.0 out of 10, Exceptional, (2)
"Nice place "
Private Home w/ Backyard + Game Table – Walk to Brady St Fun

Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

10.0 out of 10, Exceptional, (3)
"Love the indoor pool and the movie room!"
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Jackson Hotel Reviews

Find out more about Jackson

Find out more about Jackson

Everything you need to know about Jackson holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jackson holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jackson holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jackson holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jackson. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jackson holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jackson holiday rentals we have selected for you start as low as NZ$206 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jackson rentals

At Expedia, we put the best Jackson holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jackson rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jackson holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jackson. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Jackson?

Yes, there are holiday rentals close to the most popular sights in Jackson, or you can select a more secluded option if you're looking for a relaxing stay. Jackson is known for its shopping and festivals. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Jackson has to offer?

Three bedrooms upstairs : This holiday home rental outside of Jackson offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What can I see and do in Jackson?

Enjoy the area's cultural attractions such as Washington County Old Courthouse Museum, or get outdoors into nature at a spot like Big Cedar Lake. In the wider area, you’ll find Washington County Fair Grounds and Cabela's.

What are holiday rentals like in Jackson?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jackson. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family getaway.