Jackson Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Jackson holiday rentals

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$548
HK$1,986 total
includes taxes & fees
13 Apr - 14 Apr
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
9.8 out of 10, Exceptional, (36 reviews)
"Host communication was excellent. House was clean and perfect for a little weekend getaway!"
United States
Grayson P.
The price is HK$1,018
HK$2,584 total
includes taxes & fees
31 Mar - 1 Apr
Charming home w/ fire pit, walk to Lake Michigan
Dining

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (86 reviews)
"Very nice stay in a quaint place. Owner, Ryan, was very nice and hospitable."
United States
Jason D.
The price is HK$1,375
HK$1,833 total
includes taxes & fees
31 Mar - 1 Apr
Three bedrooms upstairs
Exterior

Be Still & Know, Walk to Port and Beach

Be Still & Know, Walk to Port and Beach
Port Washington
10.0 out of 10, Exceptional, (41 reviews)
"Great place to stay. Within walking distance to downtown. "
United States
Lori N.
The price is HK$930
HK$2,070 total
includes taxes & fees
31 Mar - 1 Apr
Be Still & Know, Walk to Port and Beach
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$993
HK$1,704 total
includes taxes & fees
19 Apr - 20 Apr
10 Minutes from Downtown! The Highlands Hideaway
Exterior detail

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.
Grace Adventure House, walk to Port, Lake Michigan
Property grounds

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 reviews)
"Great property and a great location. Lulu was an incredible and thoughtful host. "
United States
Lori B.
The price is HK$1,151
HK$2,320 total
includes taxes & fees
31 Mar - 1 Apr
Peaceful East Side-2 min UWM-Dining-Coffee-Parking
TV

Tucked Away Off Brady - 4 Beds

Tucked Away Off Brady - 4 Beds
Downtown Milwaukee
9.0 out of 10, Wonderful, (22 reviews)
"Great location near Brady street. Walkable to lots of shops, bars, restaurants."
United States
Andrea M.
The price is HK$384
HK$2,087 total
includes taxes & fees
6 Apr - 7 Apr
Tucked Away Off Brady - 4 Beds
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$1,151
HK$2,330 total
includes taxes & fees
5 Apr - 6 Apr
Rare East Side-2 min walk to UWM-Garage-Lake Mich
Exterior detail

Prime location in the heart of it all on Washington Ave

Prime location in the heart of it all on Washington Ave
Cedarburg
10.0 out of 10, Exceptional, (199 reviews)
"The host was very gracious and the property had all the amenities we needed. The property was clean, and the location was fantastic!"
United States
Theresa Z.
The price is HK$1,230
HK$1,558 total
includes taxes & fees
31 Mar - 1 Apr
Prime location in the heart of it all on Washington Ave
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)
"Great place to stay, close to everything "
United States
David S.
The price is HK$430
HK$1,040 total
includes taxes & fees
31 Mar - 1 Apr
Deer District Studio Apt - One Block from Fiserv and Baird
Fireplace

Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (126 reviews)
"Great location to walk to Fiserv center, clean, on-site parking, great amenities! Would love to stay here again!"
United States
Tracy
The price is HK$839
HK$1,543 total
includes taxes & fees
5 Apr - 6 Apr
Kasa Westown Milwaukee
Fridge, microwave, oven, stovetop

Luxury Historic Home - Stellar Location

Luxury Historic Home - Stellar Location
Lower East Side
9.6 out of 10, Exceptional, (27 reviews)
"A lovely historic house with three large bedrooms, a very functional kitchen, beautiful dining room and family room areas and a super fun game room. Great for family get togethers!"
United States
Donna M.
The price is HK$1,762
HK$4,405 total
includes taxes & fees
31 Mar - 1 Apr
Luxury Historic Home - Stellar Location
Interior

Near Hiking: Lakefront Getaway in Campbellsport!

Near Hiking: Lakefront Getaway in Campbellsport!
3.0 star property
Campbellsport
The price is HK$1,003
HK$3,548 total
includes taxes & fees
31 Mar - 1 Apr
Near Hiking: Lakefront Getaway in Campbellsport!
Exterior

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 reviews)
"Walking distance to several great bars, restaurants, breweries and the summer fest area. We really enjoyed our stay!"
United States
SCOTT T.
The price is HK$1,762
HK$2,576 total
includes taxes & fees
31 Mar - 1 Apr
Downtown Eastside gem near Fiserv Forum Water St Brady St
Fridge, microwave, oven, stovetop

Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything
Lower East Side
9.6 out of 10, Exceptional, (32 reviews)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is HK$1,586
HK$4,197 total
includes taxes & fees
31 Mar - 1 Apr
Stunning Upscale Retreat - Steps From Everything
Dining

Relax In Tosa—Near Downtown MKE!

Relax In Tosa—Near Downtown MKE!
Wauwatosa
The price is HK$992
HK$2,312 total
includes taxes & fees
6 Apr - 7 Apr
Relax In Tosa—Near Downtown MKE!
Dining

Quiet House

Quiet House
Milwaukee
8.0 out of 10, Very good, (10 reviews)
"Very relaxing and peaceful "
United States
Laterrance G.
The price is HK$423
HK$1,514 total
includes taxes & fees
31 Mar - 1 Apr
Quiet House
Outdoor dining

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
9.6 out of 10, Exceptional, (29 reviews)
"Was a year place to stay. Super cute and cozy inside and close to American family field"
United States
Jeannie
The price is HK$1,245
HK$2,586 total
includes taxes & fees
31 Mar - 1 Apr
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Dining

Style and Luxury - Unbeatable Location

Style and Luxury - Unbeatable Location
Lower East Side
9.6 out of 10, Exceptional, (14 reviews)
"Great location!"
United States
Mike G.
The price is HK$1,727
HK$4,105 total
includes taxes & fees
31 Mar - 1 Apr
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

Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

10/10 Excellent
"Parking was easy and free. Building is slightly run down. Staff was very nice and helpful. Would return."
Brian 3-night trip
Posted 1 hour ago
Sheraton Milwaukee Brookfield Hotel

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
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  • 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.