Jackson Holiday Rentals

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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Jackson holiday rentals

Fireplace
Kasa Westown Milwaukee

Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (118)
"Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions."
United States
Melissa
Kasa Westown Milwaukee
Billiards
ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House
4.0 star property
Westown
9.0 out of 10, Wonderful, (11)
"The room was clean and spacious and very comfy the property was as well very beautiful and so much to look at … my family enjoyed the games that were in the room as well. We will definitely stay their again for our next visit "
United States
Ivan
The price is HK$451
HK$1,279 total
includes taxes & fees
14 Dec - 15 Dec
ROVE LIVING/KL - Malt House
Terrace/patio
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
New Berlin
8.6 out of 10, Excellent, (9)
"We had an excellent family vacation at The Garden of Eden!!"
United States
Cheryl S.
The price is HK$7,807
HK$16,100 total
includes taxes & fees
15 Dec - 16 Dec
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
Dining room
ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect
3.0 star property
Lower East Side
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!"
United States
Vera
ROVE LIVING/KB - Prospect
Fridge, microwave, oven, stovetop
Wooded Hills/Indoor Pool/Hot Tub/Arcade

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Wooded Hills/Indoor Pool/Hot Tub/Arcade
Sussex
9.8 out of 10, Exceptional, (50)
"Wonderful property. Host was extremely responsive and helpful."
United States
joan r.
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Dining
Three bedrooms upstairs

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (77)
"He was very kind!"
United States
Hope
The price is HK$1,365
HK$1,821 total
includes taxes & fees
14 Dec - 15 Dec
Three bedrooms upstairs
Exterior
Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St
Downtown Milwaukee
9.0 out of 10, Wonderful, (46)
"The check in instructions were perfect and not sure he could have laid that out any better. It's a nice place close to everything. We'd stay there again. "
United States
Chad-Tara A.
The price is HK$1,945
HK$2,816 total
includes taxes & fees
28 Dec - 29 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St
Fridge, microwave, oven, stovetop
Renovated Brady St. Classic

Renovated Brady St. Classic

Renovated Brady St. Classic
Downtown Milwaukee
8.4 out of 10, Very good, (10)
"Comfortable property in a great location. Liked that my adult children could walk to nearby restaurants, shops and bars. Neighborhood parking is limited, but not unusual for downtown-type stays."
United States
Mike F.
Renovated Brady St. Classic
Interior
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
2.0 star property
Lower East Side
9.8 out of 10, Exceptional, (19)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is HK$1,022
HK$3,278 total
includes taxes & fees
16 Dec - 17 Dec
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Waukesha
9.8 out of 10, Exceptional, (17)
"Will come and stay again great host and home"
United States
Dion S.
The price is HK$1,050
HK$2,365 total
includes taxes & fees
15 Dec - 16 Dec
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything
Lower East Side
9.8 out of 10, Exceptional, (31)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is HK$1,575
HK$4,169 total
includes taxes & fees
14 Dec - 15 Dec
Stunning Upscale Retreat - Steps From Everything
Exterior
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
9.8 out of 10, Exceptional, (26)
"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 HK$1,237
HK$2,577 total
includes taxes & fees
14 Dec - 15 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Fridge, microwave, oven, stovetop
Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is HK$381
HK$2,064 total
includes taxes & fees
14 Dec - 15 Dec
Remodeled Home - Steps from Brady Street!
Exterior
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
Hartford
10.0 out of 10, Exceptional, (5)
"This is a nice place to stay. The bedrooms are all spacious, clean and very comfy. The communication with the host was great. I would stay here again. "
United States
Nicole D.
The price is HK$4,761
HK$6,503 total
includes taxes & fees
16 Dec - 17 Dec
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
Dining
The RandomCabin “On Random Lake”

The RandomCabin “On Random Lake”

The RandomCabin “On Random Lake”
Random Lake
9.8 out of 10, Exceptional, (54)
"I was a good stay. House is very clean. "
United States
Ryan E.
The RandomCabin “On Random Lake”
Property grounds
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Lower East Side
9.6 out of 10, Exceptional, (66)
"Dustin was a great host! Very easy to communicate with and the house was great as well, thanks much!"
United States
Lisa M.
The price is HK$1,477
HK$3,310 total
includes taxes & fees
15 Dec - 16 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Outdoor dining
MKE Mansion - Both Wings

MKE Mansion - Both Wings

MKE Mansion - Both Wings
Downtown Milwaukee
9.6 out of 10, Exceptional, (23)
"Great house - big group I stayed with loved it and tons of places to sleep and hang out. Fantastic location by the water and near some good restaurants. Hosts were super responsive. "
United States
Henri E.
The price is HK$7,772
HK$13,015 total
includes taxes & fees
4 Jan - 5 Jan 2026
MKE Mansion - Both Wings
Interior
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

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

Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
River Hills
8.0 out of 10, Very good, (4)
"Love the indoor pool and the movie room!"
United States
JOE C.
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
Property grounds
3-bedroom lake cottage in the Kettle Moraine State Forest

3-bedroom lake cottage in the Kettle Moraine State Forest

3-bedroom lake cottage in the Kettle Moraine State Forest
Campbellsport
9.8 out of 10, Exceptional, (44)
"Very relaxing, great fishing!"
United States
Melany D.
3-bedroom lake cottage in the Kettle Moraine State Forest
Fridge, microwave, oven, stovetop
Style and Luxury - Unbeatable Location

Style and Luxury - Unbeatable Location

Style and Luxury - Unbeatable Location
Lower East Side
9.6 out of 10, Exceptional, (13)
"Great location!"
United States
Mike G.
The price is HK$1,715
HK$4,095 total
includes taxes & fees
13 Dec - 14 Dec
Style and Luxury - Unbeatable Location
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

Hyatt Place Milwaukee/Downtown

Hyatt Place Milwaukee/Downtown

10/10 Excellent
"Very well taken care of"
joe 1-night trip
Posted 20 hours ago
Hyatt Place Milwaukee/Downtown

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?

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18: 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 7 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 a selection of games 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.