Jackson Vacation Rentals

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Check prices for these dates

Tonight
Dec 16 - Dec 17
Tomorrow
Dec 17 - Dec 18
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Jackson vacation rentals

Interior
Modern Studio by Brady St & Milwaukee Lakefront

Modern Studio by Brady St & Milwaukee Lakefront

Modern Studio by Brady St & Milwaukee Lakefront
2.0 star property
Lower East Side
8.0 out of 10, Very Good, (3)
"Enjoyed the stay here very much! Host was very quick with communication as well. Would highly recommend !"
United States
Younique T.
The price is ￥5,720
￥20,939 total
includes taxes & fees
Dec 23 - Dec 24
Modern Studio by Brady St & Milwaukee Lakefront
Interior
Comfort Near Historic Pabst Brewery & Fiserv

Comfort Near Historic Pabst Brewery & Fiserv

Comfort Near Historic Pabst Brewery & Fiserv
2.0 star property
Westown
9.4 out of 10, Exceptional, (14)
"Check-in and parking were easy. Kitchen was well stocked and included some spices. Location was perfect to catch some Brewers games. Beds were comfortable. Will stay again!"
United States
Debra D.
The price is ￥8,305
￥25,410 total
includes taxes & fees
Dec 17 - Dec 18
Comfort Near Historic Pabst Brewery & Fiserv
Interior
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking

Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking

Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
Westown
10.0 out of 10, Exceptional, (1)
"Great location to the concert and lots to do around the area. Safe place and area"
United States
Timothy S.
The price is ￥8,102
￥23,759 total
includes taxes & fees
Dec 17 - Dec 18
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
Smart TV
Vibrant Milwaukee Townhome near Downtown

Vibrant Milwaukee Townhome near Downtown

Vibrant Milwaukee Townhome near Downtown
Riverwest
8.0 out of 10, Very Good, (2)
"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 ￥11,140
￥40,692 total
includes taxes & fees
Dec 17 - Dec 18
Vibrant Milwaukee Townhome near Downtown
Dining
King Bed - Near Froedtert - FAST WiFi

King Bed - Near Froedtert - FAST WiFi

King Bed - Near Froedtert - FAST WiFi
Wauwatosa
10.0 out of 10, Exceptional, (16)
"Everything was as advertised. Very nice area of Wawatosa. "
United States
seeton p.
The price is ￥11,006
￥39,681 total
includes taxes & fees
Dec 19 - Dec 20
King Bed - Near Froedtert - FAST WiFi
Hallway
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 ￥8,881
￥25,429 total
includes taxes & fees
Dec 18 - Dec 19
ROVE LIVING/KL - Malt House
Fridge, microwave, oven, stovetop
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking

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

Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking
2.0 star property
Westown
10.0 out of 10, Exceptional, (5)
"Great room "
United States
julio
The price is ￥8,991
￥22,925 total
includes taxes & fees
Dec 21 - Dec 22
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking
Private kitchen
2BR apt w/ laundry + parking

2BR apt w/ laundry + parking

2BR apt w/ laundry + parking
Murray Hill
10.0 out of 10, Exceptional, (12)
"The apartment is clean, spacious and close to the activities we were in town for."
United States
Kelly S.
The price is ￥10,076
￥24,673 total
includes taxes & fees
Jan 5 - Jan 6, 2026
2BR apt w/ laundry + parking
Smart TV
Tosa's Cozy Corner - Pet & Family Friendly, Walkable, Near Downtown Tosa & MKE!

Tosa's Cozy Corner - Pet & Family Friendly, Walkable, Near Downtown Tosa & MKE!

Tosa's Cozy Corner - Pet & Family Friendly, Walkable, Near Downtown Tosa & MKE!
Wauwatosa
8.4 out of 10, Very Good, (7)
"Loved the 2 coffee shops in walking distance. Pizza place was only 5 minutes away too. "
United States
Ramona T.
The price is ￥7,758
￥30,369 total
includes taxes & fees
Dec 17 - Dec 18
Tosa's Cozy Corner - Pet & Family Friendly, Walkable, Near Downtown Tosa & MKE!
Lobby
Deer District Studio Apt - One Block from Fiserv and Baird

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, (2)
"Room was spotless and had great amenities. Great location. "
United States
Philip
The price is ￥8,371
￥19,535 total
includes taxes & fees
Dec 17 - Dec 18
Deer District Studio Apt - One Block from Fiserv and Baird
Exterior
Grace Adventure House, walk to Port, Lake Michigan

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)
"Easy check in and check out!"
United States
Yvonne V.
The price is ￥15,067
￥36,455 total
includes taxes & fees
Dec 17 - Dec 18
Grace Adventure House, walk to Port, Lake Michigan
Dining
Brewery District Luxe 2BR Near Fiserv with Parking

Brewery District Luxe 2BR Near Fiserv with Parking

Brewery District Luxe 2BR Near Fiserv with Parking
Westown
9.4 out of 10, Exceptional, (6)
"Great location! Super-cool historic building. Easy booking and check-in process, and responsive host. We will be back!"
United States
Christy M.
The price is ￥9,766
￥24,709 total
includes taxes & fees
Dec 21 - Dec 22
Brewery District Luxe 2BR Near Fiserv with Parking
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 ￥11,471
￥46,055 total
includes taxes & fees
Dec 29 - Dec 30
Remodeled Home - Steps from Brady Street!
Dining
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
Downtown Milwaukee
10.0 out of 10, Exceptional, (1)
"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 ￥8,991
￥20,249 total
includes taxes & fees
Dec 21 - Dec 22
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
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

Charming 2-bedroom house with everything you need in the heart of West Allis
West Allis
9.6 out of 10, Exceptional, (4)
"Had a great weekend stay. House was clean and cute and our host was very accommodating!"
United States
Renee W.
The price is ￥16,048
￥34,607 total
includes taxes & fees
Dec 22 - Dec 23
Charming 2-bedroom house with everything you need in the heart of West Allis
Exterior
Rare East Side-2 min walk to UWM-Garage-Lake Mich

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)
"Loved our stay. Nice clean place that was well stocked."
United States
Patty S.
The price is ￥22,786
￥44,043 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Rare East Side-2 min walk to UWM-Garage-Lake Mich
Property grounds
Peaceful East Side-2 min UWM-Dining-Coffee-Parking

Peaceful East Side-2 min UWM-Dining-Coffee-Parking

Peaceful East Side-2 min UWM-Dining-Coffee-Parking
Upper East Side
10.0 out of 10, Exceptional, (5)
"Great property and a great location. Lulu was an incredible and thoughtful host. "
United States
Lori B.
The price is ￥22,786
￥44,043 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Peaceful East Side-2 min UWM-Dining-Coffee-Parking
1 bedroom, desk, iron/ironing board, free WiFi
King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking

King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking

King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking
Wauwatosa
10.0 out of 10, Exceptional, (4)
"Came to the Milwaukee area for a family function and Ian’s place was perfect. Convenient to everything you need and underground parking was a nice perk. Would check his place out for any return trips."
United States
Jane H.
The price is ￥9,611
￥37,079 total
includes taxes & fees
Dec 18 - Dec 19
King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking
Exterior
10 Minutes from Downtown! The Highlands Hideaway

10 Minutes from Downtown! The Highlands Hideaway

10 Minutes from Downtown! The Highlands Hideaway
Wauwatosa
10.0 out of 10, Exceptional, (1)
"Clean old place but very nice. "
United States
Jake K.
The price is ￥19,643
￥33,726 total
includes taxes & fees
Jan 4 - Jan 5, 2026
10 Minutes from Downtown! The Highlands Hideaway
Beach nearby
Charming home w/ fire pit, walk to Lake Michigan

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, (34)
"Great location. We attended a Brewers game and made it up to Lambeau Field. So many restaurants within walking distance and the Metro market was right around the corner. Great spot!"
United States
Kathy M.
The price is ￥20,151
￥51,486 total
includes taxes & fees
Dec 17 - Dec 18
Charming home w/ fire pit, walk to Lake Michigan
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

Aloft Milwaukee Downtown

Aloft Milwaukee Downtown

10/10 Excellent
"Clean"
Carmalita 1-night trip
Posted 2 days ago
Aloft 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:

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Frequently asked questions

Can I find vacation rentals in Jackson?

Yes, we offer vacation rentals near popular points of interest in Jackson, or you can choose 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 vacation home rentals that Jackson has to offer?

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18: This vacation home rental near Jackson offers an indoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 larger area, you’ll find Washington County Fair Grounds and Cabela's.

What are vacation rentals like in Jackson?

Vacation rentals are private properties you can stay in for a couple days or more in Jackson. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for families.