Jackson Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Jackson vacation rentals

Fireplace
Kasa Westown Milwaukee

Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (119)
"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
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
7.8 out of 10, Good, (10)
"Awesome place!"
United States
Daniel M.
The price is ￥125,419
￥282,029 total
includes taxes & fees
Dec 22 - Dec 23
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
Dining
Three bedrooms upstairs

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (78)
"He was very kind!"
United States
Hope
The price is ￥27,204
￥36,280 total
includes taxes & fees
Dec 18 - Dec 19
Three bedrooms upstairs
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
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
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 ￥34,823
￥51,092 total
includes taxes & fees
Dec 27 - Dec 28
Downtown Eastside gem near Fiserv Forum Water St Brady St
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, (67)
"It was clean and close to our wedding venue. "
United States
Kathy H.
The price is ￥30,575
￥67,435 total
includes taxes & fees
Dec 18 - Dec 19
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
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, (20)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is ￥21,451
￥66,712 total
includes taxes & fees
Dec 18 - Dec 19
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
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 ￥100,601
￥136,334 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
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 ￥31,341
￥82,937 total
includes taxes & fees
Dec 28 - Dec 29
Stunning Upscale Retreat - Steps From Everything
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, (19)
"Will come and stay again great host and home"
United States
Dion S.
The price is ￥23,216
￥48,795 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
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 ￥24,608
￥51,640 total
includes taxes & fees
Jan 14 - Jan 15, 2026
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Dining
One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails

One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails

One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails
Richfield
10.0 out of 10, Exceptional, (20)
"Beautiful home with beautiful surroundings. Beautiful home great place to stay."
United States
Melissa H.
One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails
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 ￥154,855
￥253,843 total
includes taxes & fees
Dec 21 - Dec 22
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
301- Condo for 10 by Old World 3rd St/Fiserv Forum

301- Condo for 10 by Old World 3rd St/Fiserv Forum

301- Condo for 10 by Old World 3rd St/Fiserv Forum
Westown
9.8 out of 10, Exceptional, (8)
"Great place to stay"
United States
Jaclyn S.
The price is ￥30,847
￥51,378 total
includes taxes & fees
Jan 3 - Jan 4, 2026
301- Condo for 10 by Old World 3rd St/Fiserv Forum
Terrace/patio
Brady St Retreat! 4BR House w Patio & Fenced Yard

Brady St Retreat! 4BR House w Patio & Fenced Yard

Brady St Retreat! 4BR House w Patio & Fenced Yard
Lower East Side
8.0 out of 10, Very Good, (2)
"Perfect property!!!!"
United States
Carl W.
Brady St Retreat! 4BR House w Patio & Fenced Yard
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

Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

10/10 Excellent
"good variety, omelet station eggs were greasy not very good omelet, everything else was good"
linda 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Milwaukee Brookfield

Find out more about Jackson

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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.