Jackson Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Jackson holiday rentals

Fridge, microwave, oven, stovetop

Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is HK$438
HK$2,148 total
includes taxes & fees
16 Feb - 17 Feb
Remodeled Home - Steps from Brady Street!
Smart TV

Vibrant Milwaukee Townhome near Downtown

Vibrant Milwaukee Townhome near Downtown
Riverwest
8.0 out of 10, Very good, (2 reviews)
"This is a cool, fun neighborhood! It’s really central to pretty much everything and close to downtown. The property is cozy and is a nice place to hang out. We had a wonderful time! "
United States
Thomas S.
The price is HK$430
HK$1,871 total
includes taxes & fees
15 Feb - 16 Feb
Vibrant Milwaukee Townhome near Downtown
TV

Tucked Away Off Brady - 4 Beds

Tucked Away Off Brady - 4 Beds
Downtown Milwaukee
9.0 out of 10, Wonderful, (19 reviews)
"The place was spotless when we arrived and it had everything we needed for a comfortable stay. It was in a great location with lots to do."
United States
Ben K.
The price is HK$383
HK$2,073 total
includes taxes & fees
18 Feb - 19 Feb
Tucked Away Off Brady - 4 Beds
Private kitchen

2BR apt w/ laundry + parking

2BR apt w/ laundry + parking
Murray Hill
10.0 out of 10, Exceptional, (12 reviews)
"The apartment is clean, spacious and close to the activities we were in town for."
United States
Kelly S.
The price is HK$406
HK$1,124 total
includes taxes & fees
4 Mar - 5 Mar
2BR apt w/ laundry + parking
Dining

Quiet House

Quiet House
Milwaukee
7.6 out of 10, Good, (8 reviews)
"Very relaxing and peaceful "
United States
Laterrance G.
The price is HK$422
HK$1,511 total
includes taxes & fees
17 Feb - 18 Feb
Quiet House
Smart TV, computer monitors

Charming 2-bedroom house with everything you need in the heart of West Allis

Charming 2-bedroom house with everything you need in the heart of West Allis
West Allis
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 HK$766
HK$1,938 total
includes taxes & fees
12 Feb - 13 Feb
Charming 2-bedroom house with everything you need in the heart of West Allis
Casino

Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath

Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath
Brewers Hill
10.0 out of 10, Exceptional, (2 reviews)
"The property was lovely and well equipped. The host was responsive and communicative. Great location and easy rideshare to get anywhere. Would absolutely stay again!"
United States
Nuala J.
The price is HK$602
HK$2,037 total
includes taxes & fees
17 Feb - 18 Feb
Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath
Interior

Eclectic, Stylish, and Cozy Milwaukee Unit!

Eclectic, Stylish, and Cozy Milwaukee Unit!
Downtown Milwaukee
9.6 out of 10, Exceptional, (40 reviews)
"Great place and location. "
United States
Michael R.
The price is HK$555
HK$2,581 total
includes taxes & fees
17 Feb - 18 Feb
Eclectic, Stylish, and Cozy Milwaukee Unit!
Interior

Grace Adventure House, walk to Port, Lake Michigan

Grace Adventure House, walk to Port, Lake Michigan
Port Washington
10.0 out of 10, Exceptional, (26 reviews)
"Easy check in and check out!"
United States
Yvonne V.
The price is HK$760
HK$1,847 total
includes taxes & fees
16 Feb - 17 Feb
Grace Adventure House, walk to Port, Lake Michigan
Lobby

Deer District Studio Apt - One Block from Fiserv and Baird

Deer District Studio Apt - One Block from Fiserv and Baird
Westown
10.0 out of 10, Exceptional, (4 reviews)
"Room was spotless and had great amenities. Great location. "
United States
Philip
The price is HK$507
HK$1,082 total
includes taxes & fees
12 Feb - 13 Feb
Deer District Studio Apt - One Block from Fiserv and Baird
Dining

2-bedroom king bed, condo with AC-heat in downtown walkable Milwaukee

2-bedroom king bed, condo with AC-heat in downtown walkable Milwaukee
Downtown Milwaukee
10.0 out of 10, Exceptional, (1 review)
"Really great home makes you feel really safe ,host was amazing always were quick to respond to questions, 10/10 yall book again "
United States
Halimo M.
The price is HK$711
HK$1,695 total
includes taxes & fees
16 Feb - 17 Feb
2-bedroom king bed, condo with AC-heat in downtown walkable Milwaukee
Interior

Modern Studio by Brady St & Milwaukee Lakefront

Modern Studio by Brady St & Milwaukee Lakefront
Lower East Side
8.0 out of 10, Very good, (3 reviews)
"Enjoyed the stay here very much! Host was very quick with communication as well. Would highly recommend !"
United States
Younique T.
The price is HK$281
HK$1,047 total
includes taxes & fees
16 Feb - 17 Feb
Modern Studio by Brady St & Milwaukee Lakefront
Interior

Cream City Industrial Loft By Fiserv + Parking Q13

Cream City Industrial Loft By Fiserv + Parking Q13
Westown
10.0 out of 10, Exceptional, (1 review)
The price is HK$488
HK$1,286 total
includes taxes & fees
12 Feb - 13 Feb
Cream City Industrial Loft By Fiserv + Parking Q13
Fridge, microwave, oven, stovetop

Modern Studio Apt with Rooftop, Gym, and Parking

Modern Studio Apt with Rooftop, Gym, and Parking
Westown
10.0 out of 10, Exceptional, (5 reviews)
"It was the best location for the concert at the Fiserv. Check in was super easy, and it was so nice to have parking included. Very cozy, we loved it. "
United States
Hannah S.
The price is HK$563
HK$1,282 total
includes taxes & fees
12 Feb - 13 Feb
Modern Studio Apt with Rooftop, Gym, and Parking
Dining

King Bed - Near Froedtert - FAST WiFi

King Bed - Near Froedtert - FAST WiFi
Wauwatosa
10.0 out of 10, Exceptional, (17 reviews)
"Clean and nice location. "
United States
Jim D.
The price is HK$508
HK$1,899 total
includes taxes & fees
12 Feb - 13 Feb
King Bed - Near Froedtert - FAST WiFi
Beach nearby

Charming home w/ fire pit, walk to Lake Michigan

Charming home w/ fire pit, walk to Lake Michigan
Shorewood
10.0 out of 10, Exceptional, (35 reviews)
"Property was in excellent shape. Great location. Owner was an excellent communicator. Really nice day."
United States
Steve K.
The price is HK$1,016
HK$2,597 total
includes taxes & fees
19 Feb - 20 Feb
Charming home w/ fire pit, walk to Lake Michigan
Iron/ironing board, WiFi, bed sheets

Relaxing Stay Near DT | Near Lakefront & Culture

Relaxing Stay Near DT | Near Lakefront & Culture
Lower East Side
10.0 out of 10, Exceptional, (1 review)
"Host and cleaning staff were wellcoming."
United States
James T S.
The price is HK$280
HK$1,047 total
includes taxes & fees
12 Feb - 13 Feb
Relaxing Stay Near DT | Near Lakefront & Culture
Exterior

10 Minutes from Downtown! The Highlands Hideaway

10 Minutes from Downtown! The Highlands Hideaway
Wauwatosa
10.0 out of 10, Exceptional, (1 review)
"Clean old place but very nice. "
United States
Jake K.
The price is HK$957
HK$1,653 total
includes taxes & fees
22 Feb - 23 Feb
10 Minutes from Downtown! The Highlands Hideaway
Exterior

Rare East Side-2 min walk to UWM-Garage-Lake Mich

Rare East Side-2 min walk to UWM-Garage-Lake Mich
Upper East Side
10.0 out of 10, Exceptional, (2 reviews)
"Loved our stay. Nice clean place that was well stocked."
United States
Patty S.
The price is HK$1,149
HK$2,221 total
includes taxes & fees
12 Feb - 13 Feb
Rare East Side-2 min walk to UWM-Garage-Lake Mich
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jackson Hotel Reviews

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

10/10 Excellent
"Room was very clean and the staff were incredibly kind!!!worth a stay if you’re in the area :)"
Milana 2-night trip
Posted 2 days ago
Hyatt Regency Milwaukee

Find out more about Jackson

Search for holiday rentals in Jackson on Expedia! You can easily find your home rentals, villas, holiday apartments in Jackson using one of the methods below:

  • View our selection of featured holiday rentals in Jackson
  • Use the map to find apartments and other holiday homes in the Jackson neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jackson while they last

Look no further and take a look at our great range of rental properties in Jackson!

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.