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Jackson Holiday Rentals

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Our top choices for Jackson holiday rentals

1. 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, (213 reviews)
"Ideal location for all the shops and restaurants. Walking distance to all places we wanted to go."
United States
Linda H.
The price is NZ$348
includes taxes & fees
13 Sept - 14 Sept
Prime location in the heart of it all on Washington Ave

2. Charming duplex walkable to historic downtown Cedarburg

Charming duplex walkable to historic downtown Cedarburg
Cedarburg
10.0 out of 10, Exceptional, (30 reviews)
"Very clean, easy check in/check out. Great location easy to walk to downtown shops and restaurants. Would stay again !"
United States
Jennifer H.
The price is NZ$553
includes taxes & fees
30 Aug - 31 Aug
Charming duplex walkable to historic downtown Cedarburg

3. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Eclectic Hubertus Home w/ Game Room & Fire Pit!
Hubertus
9.8 out of 10, Exceptional, (27 reviews)
"We had a wonderful stay! It was the perfect Thanksgiving getaway for our family. "
United States
Mikaela M.
The price is NZ$1,283
includes taxes & fees
31 Aug - 1 Sept
Eclectic Hubertus Home w/ Game Room & Fire Pit!

4. The Quarters | Suite 3

The Quarters | Suite 3
Grafton
10.0 out of 10, Exceptional, (2 reviews)
"We came into town to spend time with our cousins. My son lives nearby in Cedarburg and this was a great location. Clean, modern, and comfortable furniture. Good amenities. Great communication with the host. "
United States
Cindy L.
The price is NZ$753
includes taxes & fees
25 Aug - 26 Aug
The Quarters | Suite 3

5. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Eclectic Hubertus Home w/ Game Room & Fire Pit!
3.0 star property
Hubertus
The price is NZ$1,291
includes taxes & fees
31 Aug - 1 Sept
Eclectic Hubertus Home w/ Game Room & Fire Pit!

6. The Quarters | Suite 5

The Quarters | Suite 5
Grafton
10.0 out of 10, Exceptional, (1 review)
The price is NZ$731
includes taxes & fees
25 Aug - 26 Aug
The Quarters | Suite 5

7. Remodeled Luxury 3BR - Walk to Cedarburg Downtown

Remodeled Luxury 3BR - Walk to Cedarburg Downtown
Cedarburg
10.0 out of 10, Exceptional, (9 reviews)
"Clean, cozy and close to downtown! Our host was easy to contact and able to accommodate an earlier check in. Perfect place to stay for our annual getaway! Thanks Brynn!"
United States
Daniel Y.
The price is NZ$765
includes taxes & fees
22 Sept - 23 Sept
Remodeled Luxury 3BR - Walk to Cedarburg Downtown

8. King Bed! Family-Friendly, Minutes from Holy Hill, Hiking+Skiing + Golf

King Bed! Family-Friendly, Minutes from Holy Hill, Hiking+Skiing + Golf
Hartford
10.0 out of 10, Exceptional, (10 reviews)
"Great place."
United States
Shawn T.
The price is NZ$755
includes taxes & fees
8 Sept - 9 Sept
King Bed! Family-Friendly, Minutes from Holy Hill, Hiking+Skiing + Golf

9. Walkable Thiensville Retreat Near Hiking!

Walkable Thiensville Retreat Near Hiking!
Thiensville
10.0 out of 10, Exceptional, (22 reviews)
"Best Vrbo we've stayed in!"
United States
John L.
The price is NZ$842
includes taxes & fees
20 Sept - 21 Sept
Walkable Thiensville Retreat Near Hiking!

10. Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (48 reviews)
"We had a wonderful stay! Loved the decor! Connie and Jim are wonderful hosts."
United States
Sara Z.
The price is NZ$318
includes taxes & fees
26 Aug - 27 Aug
Gleason's Chouse

11. Grace Adventure House, Family & Dog Friendly, Walk to Port, Shops, & the Beach!

Grace Adventure House, Family & Dog Friendly, Walk to Port, Shops, & the Beach!
Port Washington
10.0 out of 10, Exceptional, (27 reviews)
"Easy check in and check out!"
United States
Yvonne V.
The price is NZ$512
includes taxes & fees
14 Sept - 15 Sept
Grace Adventure House, Family & Dog Friendly, Walk to Port, Shops, & the Beach!

12. The Quarters | Suite 1

The Quarters | Suite 1
Grafton
10.0 out of 10, Exceptional, (2 reviews)
"Everything was clean and very easy to get around in a wheelchair "
United States
Phillip S.
The price is NZ$788
includes taxes & fees
25 Aug - 26 Aug
The Quarters | Suite 1

13. Be Still & Know, Luxury Apartment, Dog-friendly, Walk to Port, Shops, & Beach!

Be Still & Know, Luxury Apartment, Dog-friendly, Walk to Port, Shops, & Beach!
Port Washington
10.0 out of 10, Exceptional, (47 reviews)
"Everything was wonderful, clean and well presented. My girls and I, and the pup enjoyed our stay very much. "
United States
dj V.
The price is NZ$535
includes taxes & fees
25 Aug - 26 Aug
Be Still & Know, Luxury Apartment, Dog-friendly, Walk to Port, Shops, & Beach!

14. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Milwaukee WI
9.4 out of 10, Exceptional, (40 reviews)
"I’ll return for sure."
United States
William
The price is NZ$157
includes taxes & fees
1 Sept - 2 Sept
1 King Bed | Non-Smoking, Kitchen

15. Walkable Thiensville Retreat Near Hiking!

Walkable Thiensville Retreat Near Hiking!
3.0 star property
Thiensville
The price is NZ$860
includes taxes & fees
20 Sept - 21 Sept
Walkable Thiensville Retreat Near Hiking!

16. King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking

King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking
Wauwatosa
8.4 out of 10, Very good, (5 reviews)
"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 NZ$404
includes taxes & fees
25 Aug - 26 Aug
King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking

17. Quiet House

Quiet House
Milwaukee
8.0 out of 10, Very good, (17 reviews)
"Great stay . Love the location "
United States
Laterrance G.
The price is NZ$350
includes taxes & fees
1 Sept - 2 Sept
Quiet House

18. The Quarters | Suite 4

The Quarters | Suite 4
Grafton
9.8 out of 10, Exceptional, (7 reviews)
"Would highly recommend this spot to anyone. It is in a great location. This unit had designated parking which was a plus. The unit was clean, and had everything we needed. If your thinking about staying in Grafton this place is a gem. "
United States
Chelly P.
The price is NZ$734
includes taxes & fees
31 Aug - 1 Sept
The Quarters | Suite 4

19. 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, (17 reviews)
"Had a great weekend stay. House was clean and cute and our host was very accommodating!"
United States
Renee W.
The price is NZ$397
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house with everything you need in the heart of West Allis

20. Eclectic, Stylish, and Cozy Milwaukee Unit!

Eclectic, Stylish, and Cozy Milwaukee Unit!
Downtown Milwaukee
9.6 out of 10, Exceptional, (47 reviews)
"Property is just like pictures and excellent location. Would stay again."
United States
Emily T.
The price is NZ$570
includes taxes & fees
25 Aug - 26 Aug
Eclectic, Stylish, and Cozy Milwaukee Unit!
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

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 are some of the best holiday rentals that Jackson has to offer?

One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails: This holiday home rental outside of Jackson is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.