A large, historic building with a dome and columns, an American flag, and a well-maintained lawn.

Jackson Holiday Rentals

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Our top choices for Jackson holiday rentals

1. 2 Bedroom Apartment In Estherville-Steps to 2nd level

2 Bedroom Apartment In Estherville-Steps to 2nd level
Estherville
9.8 out of 10, Exceptional, (8 reviews)
"Very clean and comfortable place in a great location."
United States
Barbara P.
The price is NZ$216
includes taxes & fees
29 Aug - 30 Aug
2 Bedroom Apartment In Estherville-Steps to 2nd level

2. Charming remodeled 4-Bedroom home with fire pit

Charming remodeled 4-Bedroom home with fire pit
Spirit Lake
10.0 out of 10, Exceptional, (23 reviews)
"Perfect size and location for a family ice fishing trip. Cozy and comfortable, all the amenities you would need, and close to lots of dining options. "
United States
Clint C.
The price is NZ$708
includes taxes & fees
17 Aug - 18 Aug
Charming remodeled 4-Bedroom home with fire pit

3. Cute little cottage in the best location.

Cute little cottage in the best location.
Arnolds Park
9.6 out of 10, Exceptional, (9 reviews)
"Great place to stay for our vacation."
United States
Lynn F.
The price is NZ$299
includes taxes & fees
17 Aug - 18 Aug
Cute little cottage in the best location.

4. 3-bedroom house in marvelous Estherville with AC, WiFi. Enjoy your stay

3-bedroom house in marvelous Estherville with AC, WiFi. Enjoy your stay
Estherville
10.0 out of 10, Exceptional, (14 reviews)
"Well cared for, clean, right in a central location! "
United States
Nicholas T.
The price is NZ$338
includes taxes & fees
24 Aug - 25 Aug
3-bedroom house in marvelous Estherville with AC, WiFi. Enjoy your stay

5. Poolside Retreat at Bridges Bay

Poolside Retreat at Bridges Bay
Arnolds Park
10.0 out of 10, Exceptional, (3 reviews)
"Very nice house. Everything was clean and well stocked. "
United States
Bill A.
The price is NZ$702
includes taxes & fees
23 Aug - 24 Aug
Poolside Retreat at Bridges Bay

6. Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten

Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten
Arnolds Park
10.0 out of 10, Exceptional, (156 reviews)
"The property was clean and spacious, and our host was responsive and helpful. I would definitely book here again."
United States
Mark H.
The price is NZ$685
includes taxes & fees
8 Sept - 9 Sept
Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten

7. Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays. This suite is one the 2nd level and requires guest to use stairs

Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays. This suite is one the 2nd level and requires guest to use stairs
Arnolds Park
10.0 out of 10, Exceptional, (26 reviews)
"Great location host and price. Place had everything we needed "
United States
Eric L.
The price is NZ$520
includes taxes & fees
23 Aug - 24 Aug
Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays. This suite is one the 2nd level and requires guest to use stairs

8. 2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.

2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
Arnolds Park
10.0 out of 10, Exceptional, (23 reviews)
"I loved my stay at stay suites. Very clean, everything that was promised was there. No complaints. Will stay there again this summer if the availability is there."
United States
Chris
The price is NZ$338
includes taxes & fees
17 Aug - 18 Aug
2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.

9. A cottage collection inspired by the performing arts heritage of Okoboji Summer Theatre

A cottage collection inspired by the performing arts heritage of Okoboji Summer Theatre
Okoboji
The price is NZ$660
includes taxes & fees
17 Aug - 18 Aug
A cottage collection inspired by the performing arts heritage of Okoboji Summer Theatre

10. Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.

Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.
Arnolds Park
10.0 out of 10, Exceptional, (33 reviews)
"Nice place for family time"
United States
Cheryl Groen G.
The price is NZ$479
includes taxes & fees
17 Aug - 18 Aug
Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.

11. 2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.

2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.
Arnolds Park
9.2 out of 10, Wonderful, (22 reviews)
"Great location. Host was accommodating and helpful. "
United States
Christine R.
The price is NZ$464
includes taxes & fees
7 Sept - 8 Sept
2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.

12. The Hook Wine and Sinker House at Bridges Bay Resort

The Hook Wine and Sinker House at Bridges Bay Resort
Arnolds Park
9.8 out of 10, Exceptional, (17 reviews)
"Great house & great location! We really enjoyed our stay & will be back next year."
United States
Angie S.
The price is NZ$875
includes taxes & fees
7 Sept - 8 Sept
The Hook Wine and Sinker House at Bridges Bay Resort

13. 1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.

1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.
Arnolds Park
10.0 out of 10, Exceptional, (23 reviews)
"Very clean, great location, quick responses from host. Great stay!"
United States
Janean S.
The price is NZ$602
includes taxes & fees
23 Aug - 24 Aug
1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.

14. 1 Bedroom Suite-Stay Suites-Hwy 71 Arnolds Park <br>This suite is on the 2nd floor and does require the guest to do stairs.

1 Bedroom Suite-Stay Suites-Hwy 71 Arnolds Park <br>This suite is on the 2nd floor and does require the guest to do stairs.
Arnolds Park
9.8 out of 10, Exceptional, (27 reviews)
"Very good location, clean, great amenities."
United States
Jill H.
The price is NZ$338
includes taxes & fees
17 Aug - 18 Aug
1 Bedroom Suite-Stay Suites-Hwy 71 Arnolds Park <br>This suite is on the 2nd floor and does require the guest to do stairs.

15. Beachy Keen at Bridges Bay Resort

Beachy Keen at Bridges Bay Resort
Arnolds Park
10.0 out of 10, Exceptional, (3 reviews)
"The overall condo was clean and spacious! We had a wonderful stay! The condo faces the water and there was easy access for my grandkids to fish in the morning. There were yard games for us to use so the kids loved that! Plenty of linens and blankets as it got pretty chilly Labor Day weekend. There were plenty of kitchen pans to make breakfast in the morning and the grill was great to grill food for lunch! Great Condo! We will be back!"
United States
Sueann F.
The price is NZ$612
includes taxes & fees
27 Aug - 28 Aug
Beachy Keen at Bridges Bay Resort

16. West Lake Okoboji Cub Cottage

West Lake Okoboji Cub Cottage
Arnolds Park
9.8 out of 10, Exceptional, (9 reviews)
"Our stay was perfect! The cottage was super clean & perfect for a weekend getaway. Location was walkable to Broadway bars and restaurants."
United States
Kyle S.
The price is NZ$806
includes taxes & fees
20 Aug - 21 Aug
West Lake Okoboji Cub Cottage

17. Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access

Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access
Spirit Lake
9.4 out of 10, Exceptional, (3 reviews)
"Wonderfully clean property with all the necessary amenities to make for a great, relaxing weekend. I highly recommend this property!"
United States
Kari S.
The price is NZ$1,198
includes taxes & fees
7 Sept - 8 Sept
Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access

18. Quick 5-min drive to West Lake from Milford

Quick 5-min drive to West Lake from Milford
Milford
9.8 out of 10, Exceptional, (99 reviews)
"Great little spot very cozy and would love to back in the future"
United States
Miguel
The price is NZ$209
includes taxes & fees
21 Aug - 22 Aug
Quick 5-min drive to West Lake from Milford

19. Artsy Tartsy Bunk House off West Lake Okoboji

Artsy Tartsy Bunk House off West Lake Okoboji
Arnolds Park
7.4 out of 10, Good, (9 reviews)
"Walking distance to many local attractions."
United States
Tracy F.
The price is NZ$597
includes taxes & fees
7 Sept - 8 Sept
Artsy Tartsy Bunk House off West Lake Okoboji

20. Welcome to Arnolds Park—a beautifully designed vacation cabin located in Bridges Bay Resort

Welcome to Arnolds Park—a beautifully designed vacation cabin located in Bridges Bay Resort
Arnolds Park
9.0 out of 10, Wonderful, (2 reviews)
"Very fun place ! We enjoyed it a lot !"
United States
Denette B.
The price is NZ$898
includes taxes & fees
8 Sept - 9 Sept
Welcome to Arnolds Park—a beautifully designed vacation cabin located in Bridges Bay Resort
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

Are there 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 riverfront and churches. Make sure you have time to check out the entertainment choices and theatres during your trip.

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

Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers : This holiday home rental outside of Jackson offers a fireplace, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Jackson?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Jackson stay.

What can I see and do in Jackson?

Little Spirit Lake and Brown Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Jackson County Courthouse and Kilen Woods State Park.

What’s a holiday rental in Jackson like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jackson. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for families.