Jackson Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Jackson holiday rentals

Apartment in Downtown Milwaukee

Tucked Away Off Brady - 4 Beds
9.0 out of 10, Wonderful, (19 reviews)
"Great location near Brady street. Walkable to lots of shops, bars, restaurants."
United States
Andrea M.
The price is NZ$432
includes taxes & fees
5 Mar - 6 Mar
Tucked Away Off Brady - 4 Beds

Holiday Home in Milwaukee

Quiet House
7.6 out of 10, Good, (8 reviews)
"Very relaxing and peaceful "
United States
Laterrance G.
The price is NZ$324
includes taxes & fees
24 Feb - 25 Feb
Quiet House
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at East Side Luxury apartments. Everything was as advertised and it was great staying close to Brady St. We would definitely stay here again."
United States
Greg W.
The price is NZ$222
includes taxes & fees
24 Feb - 25 Feb
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
10.0 out of 10, Exceptional, (4 reviews)
"Room was spotless and had great amenities. Great location. "
United States
Philip
The price is NZ$222
includes taxes & fees
24 Feb - 25 Feb
Deer District Studio Apt - One Block from Fiserv and Baird
10.0 out of 10, Exceptional, (1 review)
The price is NZ$266
includes taxes & fees
24 Feb - 25 Feb
Cream City Industrial Loft By Fiserv + Parking Q13
10.0 out of 10, Exceptional, (1 review)
"Host and cleaning staff were wellcoming."
United States
James T S.
The price is NZ$232
includes taxes & fees
1 Mar - 2 Mar
Relaxing Stay Near DT | Near Lakefront & Culture
10.0 out of 10, Exceptional, (17 reviews)
"Clean and nice location. "
United States
Jim D.
The price is NZ$406
includes taxes & fees
10 Mar - 11 Mar
King Bed - Near Froedtert - FAST WiFi
8.8 out of 10, Excellent, (9 reviews)
"Our host was great with communication and we enjoyed the stay at this unique property and appreciated the history behind the building and how it has been preserved in a modern industrial style! "
United States
Maria Doxtator
The price is NZ$264
includes taxes & fees
24 Feb - 25 Feb
Spacious Luxury 2BR Apt with Parking, Rooftop, and Gym

Apartment in Port Washington

Be Still & Know, Walk to Port and Beach
10.0 out of 10, Exceptional, (40 reviews)
"Great place to stay. Within walking distance to downtown. "
United States
Lori N.
The price is NZ$436
includes taxes & fees
25 Feb - 26 Feb
Be Still & Know, Walk to Port and Beach

Holiday Home in Downtown Milwaukee

Remodeled Home - Steps from Brady Street!
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is NZ$493
includes taxes & fees
2 Mar - 3 Mar
Remodeled Home - Steps from Brady Street!
9.4 out of 10, Exceptional, (15 reviews)
"Excellent clean place to stay!"
United States
Elizabeth
The price is NZ$298
includes taxes & fees
8 Mar - 9 Mar
Modern Luxury 1BR Apt with Rooftop, Gym, and Parking

Holiday Home in Riverwest

Three bedrooms upstairs
9.6 out of 10, Exceptional, (82 reviews)
"Cozy place with an awesome kitchen!"
United States
Lilly I.
The price is NZ$388
includes taxes & fees
24 Feb - 25 Feb
Three bedrooms upstairs
9.8 out of 10, Exceptional, (27 reviews)
"We stayed while attending the WI state fair. Quiet and safe neighborhood and really close to the fairgrounds. House was clean and easy to get to. We enjoyed our stay and the fenced in backyard was perfect for our Frenchie. "
United States
Roy W.
The price is NZ$475
includes taxes & fees
24 Feb - 25 Feb
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Trendy Studio Unit Near Riverwalk & Nightlife
Chic Studio Walk to Brady St, Beach & Downtown
9.0 out of 10, Wonderful, (4 reviews)
"Such a sweet, cozy little place with all the amenities of a large space. We loved the area it was super quiet and lots within walking distance. The neighbors were also very nice!"
United States
Debbie M.
The price is NZ$556
includes taxes & fees
26 Feb - 27 Feb
Live in Chic and Comfort: Experience Our Thoughtfully Designed 1 Bed with Loft!
9.8 out of 10, Exceptional, (36 reviews)
"Property was in excellent shape. Great location. Owner was an excellent communicator. Really nice day."
United States
Steve K.
The price is NZ$550
includes taxes & fees
24 Feb - 25 Feb
Charming home w/ fire pit, walk to Lake Michigan
10.0 out of 10, Exceptional, (1 review)
"Lorinda is a wonderful host! It was icy when I arrived and she made sure me and my pup were safe. She left notes for us and a sweet gift. We loved it so much we will be back in April. "
United States
AnnaLisa S.
The price is NZ$525
includes taxes & fees
27 Feb - 28 Feb
Cozy & Quiet, dog-friendly 2-bedroom Upper in Central Milwaukee
9.6 out of 10, Exceptional, (4 reviews)
"Had a great weekend stay. House was clean and cute and our host was very accommodating!"
United States
Renee W.
The price is NZ$364
includes taxes & fees
24 Feb - 25 Feb
Charming 2-bedroom house with everything you need in the heart of West Allis
The price is NZ$498
includes taxes & fees
2 Mar - 3 Mar
Relax In Tosa—Near Downtown MKE!
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Jackson Hotel Reviews

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$222 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?

Wooded Hills/Indoor Pool/Hot Tub/Arcade: This holiday home rental outside of Jackson offers an indoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Jackson?

Enjoy the area's cultural attractions such as 1889 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.