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Jackson Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Jackson holiday rentals

A room with a wooden floor, a red sofa, a small table with a lamp, and a painting on the wall.

1. 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, (11 reviews)
"Nice place for a Hartford golf trip."
United States
sean s.
King Bed! Family-Friendly, Minutes from Holy Hill, Hiking+Skiing + Golf
A two-story house with a garage, a covered porch, and a garden with pink flowers.

2. 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, (219 reviews)
"The property was located right on the main street so it made it very easy for shopping and dining. It was a beautiful layout for the unit with two nice bedrooms, very clean and well organized. The owners were very helpful and gracious."
United States
Pete
The price is NZ$391
includes taxes & fees
1 Nov - 2 Nov
Prime location in the heart of it all on Washington Ave
A spacious interior with a stone staircase, a large window, and a cozy seating area.

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

Eclectic Hubertus Home w/ Game Room & Fire Pit!
Hubertus
9.8 out of 10, Exceptional, (28 reviews)
"We had a wonderful stay! It was the perfect Thanksgiving getaway for our family. "
United States
Mikaela M.
The price is NZ$1,364
includes taxes & fees
9 Oct - 10 Oct
Eclectic Hubertus Home w/ Game Room & Fire Pit!
A spacious dining area with a wooden table and modern chairs, a chandelier, and a view of the backyard through large sliding glass doors.

4. Remodeled Luxury 3BR - Walk to Cedarburg Downtown

Remodeled Luxury 3BR - Walk to Cedarburg Downtown
Cedarburg
10.0 out of 10, Exceptional, (13 reviews)
"Great property and close walk to downtown"
United States
Kimberly P.
The price is NZ$782
includes taxes & fees
2 Nov - 3 Nov
Remodeled Luxury 3BR - Walk to Cedarburg Downtown
A stone building with two doors, numbered 426 and 427, and a bench outside.

5. Grace Adventure House, walk to Port, Lake Michigan

Grace Adventure House, walk to Port, Lake Michigan
Port Washington
10.0 out of 10, Exceptional, (30 reviews)
"Easy check in and check out!"
United States
Yvonne V.
Grace Adventure House, walk to Port, Lake Michigan
A wooden deck with a glass railing overlooking a snowy landscape with trees.

6. 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$1,372
includes taxes & fees
21 Oct - 22 Oct
Eclectic Hubertus Home w/ Game Room & Fire Pit!
A modern kitchen with white cabinets, a wooden countertop, stainless steel appliances, and bar stools.

7. The Quarters | Suite 5

The Quarters | Suite 5
Grafton
10.0 out of 10, Exceptional, (1 review)
The price is NZ$695
includes taxes & fees
11 Oct - 12 Oct
The Quarters | Suite 5
A modern apartment with a kitchen, dining area, and living room.

8. 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$717
includes taxes & fees
12 Oct - 13 Oct
The Quarters | Suite 4
A spacious, multi-level interior with a balcony, a laundry room, and various decorative items.

9. Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (50 reviews)
"We had a wonderful stay! Loved the decor! Connie and Jim are wonderful hosts."
United States
Sara Z.
The price is NZ$347
includes taxes & fees
11 Oct - 12 Oct
Gleason's Chouse
A stone building with a blue door, surrounded by a garden with blue flowers and a tree.

10. Be Still & Know, Walk to Port and Beach

Be Still & Know, Walk to Port and Beach
Port Washington
10.0 out of 10, Exceptional, (48 reviews)
"Everything was wonderful, clean and well presented. My girls and I, and the pup enjoyed our stay very much. "
United States
dj V.
Be Still & Know, Walk to Port and Beach
A hotel room with a bed, a bathroom with a large mirror, a sink, and a window.

11. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Milwaukee WI
9.6 out of 10, Exceptional, (37 reviews)
"I will definitely stay again"
United States
Anonymous traveller
The price is NZ$151
includes taxes & fees
17 Oct - 18 Oct
1 Queen Bed | Non-Smoking, Kitchen
May 10, 2024

12. 4 bed house on the shore of Lake Michigan

4 bed house on the shore of Lake Michigan
Belgium
9.4 out of 10, Exceptional, (83 reviews)
"Location and privacy exceptional."
United States
michael g.
The price is NZ$899
includes taxes & fees
24 Oct - 25 Oct
4 bed house on the shore of Lake Michigan
A bedroom with a bed, bedside table, lamp, and a painting of a beach scene.

13. Fast WiFi - Underground Parking - King Bed - Near Froedtert

Fast WiFi - Underground Parking - King Bed - Near Froedtert
Wauwatosa
9.8 out of 10, Exceptional, (26 reviews)
"Everything was great! I definitely book again!"
United States
Lucas Y.
The price is NZ$391
includes taxes & fees
12 Oct - 13 Oct
Fast WiFi - Underground Parking - King Bed - Near Froedtert
A modern kitchen with a large island, dark cabinetry, stainless steel appliances, and a city view through large windows.

14. Modern Luxury 1BR Apt with Rooftop, Gym, and Parking

Modern Luxury 1BR Apt with Rooftop, Gym, and Parking
Westown
9.4 out of 10, Exceptional, (31 reviews)
"Beautiful view, bright and clean, great location "
Canada
Breanna
The price is NZ$266
includes taxes & fees
2 Nov - 3 Nov
Modern Luxury 1BR Apt with Rooftop, Gym, and Parking
A wooden structure with a black latch, partially covered in snow, against a brick wall.

15. Spacious Studio near Brady St

Spacious Studio near Brady St
Lower East Side
10.0 out of 10, Exceptional, (1 review)
"It was fine"
United States
M E.
The price is NZ$397
includes taxes & fees
13 Oct - 14 Oct
Spacious Studio near Brady St
A modern kitchen with a large island, built-in appliances, and ample natural light.

16. East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge | Sleeps 4

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge | Sleeps 4
Downtown Milwaukee
9.8 out of 10, Exceptional, (9 reviews)
"We stayed for a convention downtown and this was an awesome location to walk to many bars and restaurants! We chose to Uber once parked and it was $8 per trip not bad! Would definitely stay again!"
United States
Laura H.
The price is NZ$234
includes taxes & fees
2 Nov - 3 Nov
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge | Sleeps 4
A dining area with a round table, four chairs, a wooden floor, a door, and a lamp.

17. Quiet House

Quiet House
Milwaukee
7.6 out of 10, Good, (22 reviews)
"The house was clean, the neighborhood was quiet. The house was very close to the Baird center and other places we wanted to visit."
United States
Steven
The price is NZ$372
includes taxes & fees
13 Oct - 14 Oct
Quiet House
A spacious living area with a wooden staircase, a round table with a book and certificates, and a cozy seating area with a sofa and chairs.

18. Historic, 4-bedroom house in charming Hartford

Historic, 4-bedroom house in charming Hartford
Hartford
The price is NZ$1,542
includes taxes & fees
12 Oct - 13 Oct
Historic, 4-bedroom house in charming Hartford
A modern kitchen with a large island, stainless steel sink, and pendant lights.

19. 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, (40 reviews)
"Great place and very clean"
United States
Jason d.
The price is NZ$693
includes taxes & fees
20 Oct - 21 Oct
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
A gym with treadmills, elliptical machines, and weight benches.

20. Deer District Studio Apt - One Block from Fiserv and Baird

Deer District Studio Apt - One Block from Fiserv and Baird
Westown
Deer District Studio Apt - One Block from Fiserv and Baird
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
"Old time glam with the best continental breakfast I’ve had in a very long time"
Kyra 2-night trip
Posted 3 hours ago
Embassy Suites by Hilton Milwaukee Brookfield

Find out more about Jackson

Everything you need to know about Jackson holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jackson holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jackson holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jackson holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jackson. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jackson holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jackson holiday rentals we have selected for you start as low as NZ$151 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jackson rentals

At Expedia, we put the best Jackson holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jackson rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jackson holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jackson. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Three Bedroom Upper: This holiday home rental outside of Jackson is located near the beach, and has a balcony, a garden 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. 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.