Jackson Holiday Rentals

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Holiday Rentals in Jackson

Exterior
Secluded cabins with fishing pond on the Mississippi River Hills Wine Trail
9.8 out of 10, Exceptional, (15)
"Husband I had a great stay at this cabin. Big fish in the ponds. We returned for them to get bigger yet. Cheryl checked on us and was great with communications. Would highly recommend."
Secluded cabins with fishing pond on the Mississippi River Hills Wine Trail
Fridge, microwave, oven, stovetop
Relax in the country at Countryside Villas! - Villa A
10.0 out of 10, Exceptional, (17)
"This was just what we needed for the occasion. Girls trip so 2 bathrooms a must! Met owner, very pleasant! Would definitely stay here again."
The price is NZ$264
per night
28 May - 29 May
Relax in the country at Countryside Villas! - Villa A
Property grounds
New cabin in the woods with private hot tub
10.0 out of 10, Exceptional, (72)
"Private. Clean. Cozy. Our second stay here and it was just as lovely as the first stay."
New cabin in the woods with private hot tub
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Property grounds
Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery
10.0 out of 10, Exceptional, (81)
"We absolutely adored our precious cabin! Ver clean. Outdoor amenities were awesome! Nice fire pit and clean hot tub!"
Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery
Exterior
Rest, Relax and Renew. Our log cabin experience awaits your arrival.
10.0 out of 10, Exceptional, (337)
"Very please and enjoyed our stay. I highly recommend the place. I will make a suggestion for the cleaner. My wife has a skin sensitivity and we have come accustom to using only soaps that have no smell. The bed linens and bath towels were washed with a scented detergent and for us was a bit too much. Other than that a great experience. Thank you for making a great place to get away."
The price is NZ$320
per night
28 May - 29 May
Rest, Relax and Renew. Our log cabin experience awaits your arrival.
Exterior
Exquisite views of Shawnee National Forest seen from a private, covered hot tub.
10.0 out of 10, Exceptional, (17)
"What a perfect location for a weekend getaway! Breathtaking views that were perfect for sitting with a cup of coffee and a good book. Property was clean, beautifully decorated, and had everything we needed for the weekend. Highly recommend!"
The price is NZ$539
per night
30 May - 31 May
Exquisite views of Shawnee National Forest seen from a private, covered hot tub.
Exterior
Artistic and Creative Vibe with Indoor Swing 2 Blocks to Downtown & near SEMO
9.8 out of 10, Exceptional, (17)
"Town was cute and ecclectic, stay at VRBO gave the same vibes. Very clean and fun. We only stayed for 1 night but would love to come back- stopped by Annie Laurie’s, Indie House, Kenny’s Flippin Burgers, Ebb and Flow brewery and Broadway Bistro/vintage store. We recommend all of them!"
The price is NZ$242
per night
27 May - 28 May
Artistic and Creative Vibe with Indoor Swing 2 Blocks to Downtown & near SEMO
Exterior
Notting Hill Cottage
9.6 out of 10, Exceptional, (277)
"Excellent location for hiking, exploring the wineries, or just getting away. The hot tub after a long day of hiking in the Shawnee was definitely a plus."
Notting Hill Cottage
Property grounds
Rated#1 Big Sky Cabin! 🍷 On the Wine Trail Hot Tub 🔥 FirePit Pool 🎱 Table
10.0 out of 10, Exceptional, (146)
"Our stay was great! Can't say enough about the cabin or the owner's responsiveness and care. I highly recommend!"
Rated#1 Big Sky Cabin! 🍷 On the Wine Trail Hot Tub 🔥 FirePit Pool 🎱 Table
On the Shawnee Wine Trail
10.0 out of 10, Exceptional, (173)
"The cabin was very clean and well kept. The kitchen was stocked with everything we needed to make meals while staying there. This cabin is located by itself in a wooded area. Very private, relaxing getaway. Highly recommend staying here if in the area."
On the Shawnee Wine Trail
Property grounds
Feels like your in a Tree House!On the Wine 🍷Trail! Fire🔥Pit Private Location
9.8 out of 10, Exceptional, (193)
"I loved being away from the hustle and bustle of the city. The home is cozy but the water pressure for showers was almost non existent. It would be nice to have better internet for rainy days. But overall nice stay and beautiful home and outdoor space."
Feels like your in a Tree House!On the Wine 🍷Trail! Fire🔥Pit Private Location
Fridge, microwave, oven, stovetop
Serenity South -- Gardens, River-Views, and Refreshing Space
10.0 out of 10, Exceptional, (114)
"The place was perfect for our stay and was close to the farmers market and downtown shops. Highly recommend for location!"
The price is NZ$400
per night
1 Jun - 2 Jun
Serenity South -- Gardens, River-Views, and Refreshing Space
Exterior
Winetrail Cabin - Giant City SP, SIU, Cedar Lake, & Shawnee Forest minutes away!
9.8 out of 10, Exceptional, (30)
"I really enjoyed my stay. I came to spend some time with my daughter who goes to SIU. It was nice, quiet, and had the great charm. It is a cabin so it is rustic but that was the charm of the cabin. The bed was great, we were able to cook and relax like the comforts of home. The wifi had an issue and needed to be reset and the host was very prompt on fixing the issue. He was available! I will definitely stay here again when I visit my daughter!"
Winetrail Cabin - Giant City SP, SIU, Cedar Lake, & Shawnee Forest minutes away!
Fridge, microwave, oven, stovetop
Charming 2-Story- C.1847 - River Views - Fast Wifi
9.6 out of 10, Exceptional, (10)
"Cape Girardeau is about the halfway point for us (Wisconsin) and friends from Mississippi. This VRBO is ideally located within walking distance to plenty of restaurants, shops and bars. Property is very clean, has the basics and communication with the owner was super easy. The saloon-style doors for the downstairs bathroom were a little unexpected, but we made it work. We enjoyed our stay and would recommended this property for a long weekend."
Charming 2-Story- C.1847 - River Views - Fast Wifi
Exterior
3 Minutes to Giant City - 6 Minutes to SIU - 4 Minutes to Shawnee Winetrail!
10.0 out of 10, Exceptional, (30)
"It was close to many state parks and very close to Carbondale. Very quiet "
3 Minutes to Giant City - 6 Minutes to SIU - 4 Minutes to Shawnee Winetrail!
Exterior
Stones Throw from Giant City Park, Wineries, Hiking, Biking, Hunting and more.
9.6 out of 10, Exceptional, (17)
"Had my parents in town for the weekend and needed a place that would take their bigger dog. The cabin was exactly as described! Cute little place with comfortable beds and the location was convenient. I had some trouble getting in at first (user error) but I called the host and he quickly walked me through it. Would highly recommend for a weekend get away!"
Stones Throw from Giant City Park, Wineries, Hiking, Biking, Hunting and more.
Exterior
Minutes to Giant City - SIU - Shawnee Winetrail - Shawnee Forest - Wi-Fi
9.8 out of 10, Exceptional, (21)
"Other than not having a range top the cabin had everything we could ask for! Cleanliness and location were premier."
Minutes to Giant City - SIU - Shawnee Winetrail - Shawnee Forest - Wi-Fi
Interior
Our 2nd Luxury Cabin shares Native American Charm & Contemporary Comfort
10.0 out of 10, Exceptional, (76)
"We had a great time at the cabin. It’s comfortable, clean and had everything we needed. Thank you!"
Our 2nd Luxury Cabin shares Native American Charm & Contemporary Comfort
Exterior
* Best Location on the Wine Trail! * Hiking Trail 1 min away * Wi-Fi *
10.0 out of 10, Exceptional, (80)
"Very quite and peaceful Exactly what I wanted!"
* Best Location on the Wine Trail! * Hiking Trail 1 min away * Wi-Fi *
Property grounds
Wine Trail, Cozy Cabin plus hot tub
10.0 out of 10, Exceptional, (72)
"Very clean and comfortable. Close to many wineries. Great sunset view from the hot tub. Quiet setting. Had a nice relaxing weekend. Would book again.❤️"
Wine Trail, Cozy Cabin plus hot tub
Don't see what you're looking for?
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

Property amenity
La Quinta Inn & Suites by Wyndham Jackson/Cape Girardeau
2.5 star property
9.0 out of 10, Wonderful, (375)
"A nice, clean , quiet property. Very good buy"
The price is NZ$149
per night
2 Jun - 3 Jun
La Quinta Inn & Suites by Wyndham Jackson/Cape Girardeau
Lobby
Comfort Suites Jackson-Cape Girardeau
2.5 star property
8.2 out of 10, Very good, (640)
"Clean comfortable room"
The price is NZ$172
per night
27 May - 28 May
Comfort Suites Jackson-Cape Girardeau
Lobby
Drury Inn & Suites Jackson MO
3.0 star property
9.6 out of 10, Exceptional, (960)
"The room was just as expected double bed suit with pullout bed worked great for my family of 5. Food options were grest and taste was good. Even though they were at compacity some nights, the parking lot had plenty of spots available. Dairy queen, a pizza buffet place and a gas station were right next door if you needed anything else."
The price is NZ$187
per night
28 May - 29 May
Drury Inn & Suites Jackson MO
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

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. Our travellers say Jackson has a good selection of restaurants. Make sure you have time to check out the shopping and wineries during your trip.

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

Notting Hill Cottage: This holiday home rental outside of Jackson offers a patio, a private garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Jackson?

Choose from 3 Expedia holiday rentals in Jackson for a memorable holiday.

What’s there to see and do in Jackson?

Trail of Tears State Park and Mississippi River are a couple of lovely local spots to get outside and enjoy nature. Litz Park and Steele Crest Winery are other places to visit while you're in town.

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 be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.

Recent reviews of Jackson properties
Expedia verified reviews

Auburn Place Hotel And Suites

Auburn Place Hotel And Suites

5/5 Excellent
"Always a wonderful for my wife and me at Auburn Place. We travel from Alabama to Kansas four times a year and always stay at Auburn Place. Great family atmosphere, wonderful staff, excellent breakfast, nice rooms—a great value. "
A verified traveller stayed at Auburn Place Hotel And Suites
Posted 12 hours ago
Auburn Place Hotel And Suites