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Jackson Vacation Rentals

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Our top choices for Jackson vacation 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, (217 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 CA $253
CA $311 total
includes taxes & fees
Nov 1 - Nov 2
Prime location in the heart of it all on Washington Ave

2. 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 CA $389
CA $1,121 total
includes taxes & fees
Oct 4 - Oct 5
Eclectic Hubertus Home w/ Game Room & Fire Pit!

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

Eclectic Hubertus Home w/ Game Room & Fire Pit!
3.0 star property
Hubertus
The price is CA $474
CA $1,095 total
includes taxes & fees
Oct 4 - Oct 5
Eclectic Hubertus Home w/ Game Room & Fire Pit!

4. Remodeled Luxury 3BR - Walk to Cedarburg Downtown

Remodeled Luxury 3BR - Walk to Cedarburg Downtown
Cedarburg
10.0 out of 10, Exceptional, (11 reviews)
"Great property and close walk to downtown"
United States
Kimberly P.
The price is CA $284
CA $627 total
includes taxes & fees
Oct 26 - Oct 27
Remodeled Luxury 3BR - Walk to Cedarburg Downtown

5. 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, (29 reviews)
"Easy check in and check out!"
United States
Yvonne V.
The price is CA $131
CA $347 total
includes taxes & fees
Oct 4 - Oct 5
Grace Adventure House, Family & Dog Friendly, Walk to Port, Shops, & the Beach!

6. 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, (81 reviews)
"Location and privacy exceptional."
United States
michael g.
The price is CA $96
CA $413 total
includes taxes & fees
Oct 7 - Oct 8
4 bed house on the shore of Lake Michigan

7. 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.
The price is CA $249
CA $612 total
includes taxes & fees
Oct 31 - Nov 1
King Bed! Family-Friendly, Minutes from Holy Hill, Hiking+Skiing + Golf

8. The Quarters | Suite 3

The Quarters | Suite 3
Grafton
10.0 out of 10, Exceptional, (3 reviews)
"Great clean property, easy check in, great coffee place downstairs (collectivo). Really enjoyed our stay in downtown Grafton. Would definitely stay here again. Easy access to cedarburg, Grafton, and port Washington."
United States
Steve P.
The price is CA $334
CA $591 total
includes taxes & fees
Oct 5 - Oct 6
The Quarters | Suite 3

9. The Quarters | Suite 5

The Quarters | Suite 5
Grafton
10.0 out of 10, Exceptional, (1 review)
The price is CA $319
CA $579 total
includes taxes & fees
Oct 11 - Oct 12
The Quarters | Suite 5

10. 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 CA $192
CA $270 total
includes taxes & fees
Oct 4 - Oct 5
Gleason's Chouse

11. Be Still & Know, Luxury Historic Dog-friendly Apartment, Fireplace, Walk to Port

Be Still & Know, Luxury Historic Dog-friendly Apartment, Fireplace, Walk to Port
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.
The price is CA $236
CA $495 total
includes taxes & fees
Oct 20 - Oct 21
Be Still & Know, Luxury Historic Dog-friendly Apartment, Fireplace, Walk to Port

12. Walkable Thiensville Retreat Near Hiking!

Walkable Thiensville Retreat Near Hiking!
Thiensville
10.0 out of 10, Exceptional, (24 reviews)
"Best Vrbo we've stayed in!"
United States
John L.
The price is CA $404
CA $859 total
includes taxes & fees
Oct 24 - Oct 25
Walkable Thiensville Retreat Near Hiking!

13. Walkable Thiensville Retreat Near Hiking!

Walkable Thiensville Retreat Near Hiking!
3.0 star property
Thiensville
The price is CA $491
CA $839 total
includes taxes & fees
Oct 24 - Oct 25
Walkable Thiensville Retreat Near Hiking!

14. Cottage near Mt. Mary College

Cottage near Mt. Mary College
Milwaukee
10.0 out of 10, Exceptional, (24 reviews)
"We found this to be a charming and well thought out property in a convenient location."
United States
Susan K.
The price is CA $204
CA $534 total
includes taxes & fees
Oct 4 - Oct 5
Cottage near Mt. Mary College

15. 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, (54 reviews)
"Our stay at this casita was perfect! Clean, cozy and close to our family. We’ve stayed here before and we will stay here again!"
United States
Myra K.
The price is CA $190
CA $484 total
includes taxes & fees
Oct 5 - Oct 6
Charming home w/ fire pit, walk to Lake Michigan

16. 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 CA $96
CA $300 total
includes taxes & fees
Oct 5 - Oct 6
Quiet House

17. 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 CA $102
CA $116 total
includes taxes & fees
Oct 15 - Oct 16
1 Queen Bed | Non-Smoking, Kitchen

18. New: Tremendous 4-bedroom house on private lot in charming Brookfield

New: Tremendous 4-bedroom house on private lot in charming Brookfield
Brookfield
The price is CA $275
CA $705 total
includes taxes & fees
Nov 1 - Nov 2
New: Tremendous 4-bedroom house on private lot in charming Brookfield

19. 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 CA $98
CA $309 total
includes taxes & fees
Oct 8 - Oct 9
Fast WiFi - Underground Parking - King Bed - Near Froedtert

20. Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (12 reviews)
"Great stay and great communication throughout. Would stay again, thank you!"
United States
David M.
The price is CA $102
CA $426 total
includes taxes & fees
Oct 14 - Oct 15
Remodeled Home - Steps from Brady Street!
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Jackson?

Yes, we offer vacation rentals near popular points of interest in Jackson, or you can choose 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 vacation home rentals that Jackson has to offer?

Three Bedroom Upper: This vacation home rental near Jackson is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection 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 larger area, you’ll find Washington County Fair Grounds and Cabela's.

What are vacation rentals like in Jackson?

Vacation rentals are private properties you can stay in for a couple days or more in Jackson. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for families.