Jackson Holiday Rentals

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Holiday Rentals in Jackson

Fireplace
Kasa Westown Milwaukee
4.0 star property
9.0 out of 10, Wonderful, (44)
"Awesome property with a handy vital help desk. Truly unique experience I recommend staying here"
The price is NZ$379
includes taxes & fees
29 May - 30 May
Kasa Westown Milwaukee
TV, video games
Eclectic, Stylish, and Cozy Milwaukee Unit!
10.0 out of 10, Exceptional, (4)
"Fantastic location for night life. Spacious home for our family"
The price is NZ$551
includes taxes & fees
10 Jun - 11 Jun
Eclectic, Stylish, and Cozy Milwaukee Unit!
Fridge, microwave, oven, stovetop
Amazing Five Bedroom Milwaukee Vacation Home!!
10.0 out of 10, Exceptional, (30)
"Huge pool and pool room, arcade, pool table, ping pong, what’s not to like…?"
Amazing Five Bedroom Milwaukee Vacation Home!!
Save an average of 15% on thousands of hotels when you're signed in
Fridge, microwave, oven, stovetop
Large, Private 3 Br Home | Ideal Location
9.8 out of 10, Exceptional, (15)
"Property was clean and had many beds, but only 1 bathroom (plenty of towels). It’s worth noting that the master bedroom is not actually a room with a door, but accordion dividers for separation. So if someone is watching tv in the family room, you most likely will hear it. It was easy to park on the street and I was provided instructions for getting free overnight parking so that was nice."
The price is NZ$443
includes taxes & fees
4 Jun - 5 Jun
Large, Private 3 Br Home | Ideal Location
Fridge, microwave, oven, stovetop
Nice 3 bedrooms with Free wine , parking and Wi-Fi
5.8 out of 10, (11)
"very clean"
The price is NZ$328
includes taxes & fees
29 May - 30 May
Nice 3 bedrooms with Free wine , parking and Wi-Fi
Interior
Beautifully restored lake house on the shores of Erler Lake.
9.6 out of 10, Exceptional, (188)
"Was in town for funeral. Was great place to gather with family. Right in park so was nice to go for a walk."
Beautifully restored lake house on the shores of Erler Lake.
Exterior
Booth Upper · Amazing view, Modern Space
10.0 out of 10, Exceptional, (26)
"Awesome area to have a fun time in MKE without need for vehicle"
Booth Upper · Amazing view, Modern Space
Exterior
Eclectic Lower Level Duplex | Centrally Located
9.6 out of 10, Exceptional, (14)
"It was a nice cozy stay but when we got there the house was still kinda dirty."
The price is NZ$224
includes taxes & fees
2 Jun - 3 Jun
Eclectic Lower Level Duplex | Centrally Located
Bathtub, hair dryer, towels
10min to DT + Fire Pit + Home Gym + Shuffleboard
10.0 out of 10, Exceptional, (7)
"We were in MKE for an extended family gathering and this home was perfect for our party of six. Clean, well maintained, with everything we needed to feel comfortable. Good communication with hosts. We will stay here again when visiting the area. Highly recommend."
The price is NZ$676
includes taxes & fees
29 May - 30 May
10min to DT + Fire Pit + Home Gym + Shuffleboard
Fridge, microwave, oven, stovetop
Stunning/River View Brady St Home! Loaded w Extras
9.6 out of 10, Exceptional, (48)
"Very charming property and well maintained. Easy Uber ride to venue. If it was nicer weather we could have enjoyed the deck. Definitely recommend 😊"
The price is NZ$655
includes taxes & fees
29 May - 30 May
Stunning/River View Brady St Home! Loaded w Extras
Property grounds
The RandomCabin “On Random Lake”
10.0 out of 10, Exceptional, (34)
"Dan was a very good hostess. Really enjoyed my time there. Neighbor Dave was a little overbearing and kind of intrusive...but overall, I enjoyed my stay."
The RandomCabin “On Random Lake”
Fridge, microwave, oven, stovetop
Spacious Home Perfect for Families & Groups: Near Fiserv Forum & Brady Street!
10.0 out of 10, Exceptional, (1)
"The place was as advertised and was clean and great for our group."
The price is NZ$947
includes taxes & fees
29 May - 30 May
Spacious Home Perfect for Families & Groups: Near Fiserv Forum & Brady Street!
Fridge, microwave, oven, stovetop
$89 This Week! - Mins to Froedert / State Fair
9.6 out of 10, Exceptional, (5)
"Great communication, cleanliness, and property."
The price is NZ$908
includes taxes & fees
3 Jun - 4 Jun
$89 This Week! - Mins to Froedert / State Fair
Exterior
15 minutes to anywhere in and around Milwaukee.
10.0 out of 10, Exceptional, (14)
"Very clean and cozy. Perfect for two or three people. It is a basement apartment but nice windows so it doesn't feel totally under ground. The hosts live upstairs and are very nice! Nice area outside if you want to hang out outdoors. I will definitely stay here again."
The price is NZ$268
includes taxes & fees
2 Jun - 3 Jun
15 minutes to anywhere in and around Milwaukee.
Lake
Downtown Eastside gem near Fiserv Forum Water St Brady St
9.2 out of 10, Wonderful, (15)
"Great little place to stay when we were going to a concert with friends. It was colder weather so not really walking distance to the fiserv or local bars but the uber trips were cheap. The setup of the apartment worked well for eating dinner and socializing but still gave us privacy for sleeping. Check-in and check-out were easy and the hosts communicated well and were very accommodating. Would stay here again."
The price is NZ$596
includes taxes & fees
29 May - 30 May
Downtown Eastside gem near Fiserv Forum Water St Brady St
Fitness facility
Urban Oasis minutes to Fiserv, Summerfest & more
9.8 out of 10, Exceptional, (7)
"This rental is gorgeous and spacious. The host was great with communication. Great stay."
The price is NZ$381
includes taxes & fees
5 Jun - 6 Jun
Urban Oasis minutes to Fiserv, Summerfest & more
Exterior
Modern, Spacious Home near Cedarburg - Perfect for Families and Girls' Getaways!
10.0 out of 10, Exceptional, (82)
"This is a wonderful home, close to all amenities. Grafton and Cedarburg are great places to visit. The home was clean, spacious, and well stocked for cooking. We enjoyed our stay very much."
Modern, Spacious Home near Cedarburg - Perfect for Families and Girls' Getaways!
Fridge, microwave, oven, stovetop
Tucked Away Off Brady - 4 Beds
9.0 out of 10, Wonderful, (7)
"Stayed here for a Marquette event in Milwaukee. Location was great with close proximity to Brady Street! Had everything we needed."
The price is NZ$395
includes taxes & fees
10 Jun - 11 Jun
Tucked Away Off Brady - 4 Beds
Exterior
Booth Lower · Beautiful Victorian, Amazing View!
10.0 out of 10, Exceptional, (14)
"The property was updated and clean. Nice view of the city. The neighborhood was quiet and a nice walking area for exercise. Would rent this property again."
Booth Lower · Beautiful Victorian, Amazing View!
Private kitchen
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
10.0 out of 10, Exceptional, (3)
"We loved this property! Five of us stayed for the night and had everything we needed! The apartment is spacious, has a large variety of sleeping options and is extremely clean. The decor looks exactly like the photos (even better in person!) and has all the amenities you will need, including a washer and dryer if need be. Check in was simple and seamless. The neighborhood was clean and felt very safe. The host is wonderful. She communicates quickly and was able to answer all of our questions. We...
The price is NZ$818
includes taxes & fees
5 Jun - 6 Jun
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
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See all available properties in Jackson
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.

Other types of properties in Jackson you may be interested in

Premium bedding, down duvets, in-room safe, blackout curtains
Saint Kate - The Arts Hotel
4.0 star property
9.8 out of 10, Exceptional, (1674)
"Staff was very friendly and helpful "
The price is NZ$254
includes taxes & fees
29 May - 30 May
Saint Kate - The Arts Hotel
Front of property - evening/night
Hyatt Regency Milwaukee
4.0 star property
8.2 out of 10, Very good, (1186)
"The room was very comfortable and the front desk staff helped correct my booking easily. The valets were so nice and friendly. It is located in a great location"
The price is NZ$223
includes taxes & fees
3 Jun - 4 Jun
Hyatt Regency Milwaukee
Exterior
Holiday Inn Express Milwaukee-West Medical Center, an IHG Hotel
2.5 star property
7.6 out of 10, Good, (1008)
"Great staff, delicious breakfast, close to many attractions and only 15 mins from downtown"
The price is NZ$185
includes taxes & fees
2 Jun - 3 Jun
Holiday Inn Express Milwaukee-West Medical Center, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Jackson holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Jackson. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Jackson. Seeing all the best attractions is bound to make you fall in love with Jackson. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Jackson short-term rentals, that won’t be hard to do.

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 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.

Recent reviews of Jackson properties
Expedia verified reviews