Jackson Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Holiday Rentals in Jackson

Our top choices for Jackson holiday rentals

Kasa Westown Milwaukee
Fireplace

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (94)
"Property was clean and well appointed. We enjoyed our stay."
Kasa Westown Milwaukee
KLVG - Malt House
Billiards

KLVG - Malt House

4.0 star property
9.0 out of 10, Wonderful, (9)
"Loved the uniqueness, location and cleanliness of the unit."
KLVG - Malt House
17-acre Private Oasis estate with, an indoor pool, and private lake, sleeps 16
Terrace/patio

17-acre Private Oasis estate with, an indoor pool, and private lake, sleeps 16

8.0 out of 10, Very good, (4)
"We had an excellent family vacation at The Garden of Eden!!"
17-acre Private Oasis estate with, an indoor pool, and private lake, sleeps 16
KB - Prospec
Dining room

KB - Prospec

3.0 star property
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!"
KB - Prospec
Downtown Eastside gem near Fiserv Forum Water St Brady St
Exterior

Downtown Eastside gem near Fiserv Forum Water St Brady St

9.2 out of 10, Wonderful, (41)
"Great location and super comfortable "
The price is HK$1,752
HK$2,571 total
includes taxes & fees
1 Sept - 2 Sept
Downtown Eastside gem near Fiserv Forum Water St Brady St
Newly Remodeled Home!! Five minutes from Downtown Milwaukee
Fridge, microwave, stovetop, coffee/tea maker

Newly Remodeled Home!! Five minutes from Downtown Milwaukee

8.2 out of 10, Very good, (43)
"House was clean and was very spacious."
The price is HK$895
HK$1,524 total
includes taxes & fees
30 Aug - 31 Aug
Newly Remodeled Home!! Five minutes from Downtown Milwaukee
Charming 3-bedroom house with AC and WiFi in marvelous Milwaukee
Living area

Charming 3-bedroom house with AC and WiFi in marvelous Milwaukee

2.0 out of 10, (1)
"The doorbell was ripped off and there's a realtor's lock on the doorknob. The house was double booked and people that had it booked for Friday & Saturday were already there - I had it booked for Saturday night only. I was charged for the full amount & then got a partial refund, and the owner booked me for the following 2 nights after I had already driven home! After a call to VRBO, I did get a full refund and the other reservations were unauthorized and canceled. Be aware!"
The price is HK$1,226
HK$1,914 total
includes taxes & fees
30 Aug - 31 Aug
Charming 3-bedroom house with AC and WiFi in marvelous Milwaukee
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Fridge, microwave, oven, stovetop

Wooded Hills/Indoor Pool/Hot Tub/Arcade

9.8 out of 10, Exceptional, (48)
"House was clean and spacious. Pool and extra amenities were great!"
Wooded Hills/Indoor Pool/Hot Tub/Arcade
4 bed house on the shore of Lake Michigan
On the beach

4 bed house on the shore of Lake Michigan

9.4 out of 10, Exceptional, (61)
"excellent lake access and views"
4 bed house on the shore of Lake Michigan
Beautiful Tent at Camp Northern Lights!
Exterior

Beautiful Tent at Camp Northern Lights!

9.4 out of 10, Exceptional, (12)
"Beautiful location"
Beautiful Tent at Camp Northern Lights!
Three bedrooms upstairs
Dining

Three bedrooms upstairs

9.6 out of 10, Exceptional, (71)
"Fantastic stay and loved all of the craftsman architecture. We loved the neighborhood and it's close to great eateries. Thanks Ryan!"
The price is HK$1,717
HK$2,318 total
includes taxes & fees
31 Aug - 1 Sept
Three bedrooms upstairs
Cozy 2 Bedroom Downtown Milwaukee Apartment
Interior

Cozy 2 Bedroom Downtown Milwaukee Apartment

9.4 out of 10, Exceptional, (3)
"Cute apartment, good location. Less kitchenware than expected and it was scratched nonstick. Air conditioning is glorious - not throttled to lukewarm like some short term rentals. Owners are part of the no-topsheet trend, which has fans and non-fans. Mattresses are very comfortable. "
Cozy 2 Bedroom Downtown Milwaukee Apartment
Quiet House
Fridge, microwave, oven, stovetop

Quiet House

8.0 out of 10, Very good, (4)
"Great stay for attending Summerfest. Short trip to the festival. Place was tidy and comfortable."
The price is HK$740
HK$1,919 total
includes taxes & fees
2 Sept - 3 Sept
Quiet House
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
Interior

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

9.0 out of 10, Wonderful, (2)
"Everything was great!"
The price is HK$382
HK$981 total
includes taxes & fees
31 Aug - 1 Sept
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
3-bedroom lake cottage in the Kettle Moraine State Forest
Property grounds

3-bedroom lake cottage in the Kettle Moraine State Forest

9.8 out of 10, Exceptional, (42)
"Enjoyed our stay. Appreciated the lake rules limited wake time which ensured a relaxing stay,"
3-bedroom lake cottage in the Kettle Moraine State Forest
Stunning Upscale Retreat - Steps From Everything
Fridge, microwave, oven, stovetop

Stunning Upscale Retreat - Steps From Everything

9.8 out of 10, Exceptional, (28)
"Great location and super clean property. Highly recommend."
The price is HK$1,542
HK$4,131 total
includes taxes & fees
1 Sept - 2 Sept
Stunning Upscale Retreat - Steps From Everything
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Property grounds

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

9.4 out of 10, Exceptional, (61)
"Great house for 6 adults and 2 babies for a long weekend stay! An easy walk to shops, grocery stores and restaurants on Brady St and slightly longer but very nice walk to downtown and the riverwalk. Ample space, quiet surroundings and everything we needed for a nice weekend! "
The price is HK$1,121
HK$2,874 total
includes taxes & fees
8 Sept - 9 Sept
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
Interior

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

10.0 out of 10, Exceptional, (2)
"Easy to work with and beautiful home! "
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Interior

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

2.0 star property
9.8 out of 10, Exceptional, (13)
"A group of 8 friends stayed here while visiting Milwaukee for a wedding. We enjoyed the stay and would stay there again in the future! Tonga was always very responsive and friendly and helped quickly when an issue arose. "
The price is HK$1,191
HK$3,544 total
includes taxes & fees
22 Sept - 23 Sept
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Beautiful Lake House in County Park
Dining

Beautiful Lake House in County Park

9.6 out of 10, Exceptional, (211)
"The home is cozy and spacious. It is in a park so the kids went fishing and walked the paths. It was still cold out so we didn’t use the beautiful beach area. Lake is very clear. I highly recommend staying here. "
Beautiful Lake House in County Park
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

Find out more about Jackson

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!

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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?

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find: This holiday home rental outside of Jackson is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

What can I see and do in Jackson?

Enjoy the area's cultural attractions such as Washington County Old 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.