Holiday rentals in Jackson

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Top-rated holiday rentals in Jackson

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Top guest favourite
The cabin is set in a secluded wooded area, surrounded by tall trees and colorful foliage. Its exterior features a combination of wood and stone, with a sloped blue metal roof. Sunlight filters through the trees, casting dappled shadows on the ground.
Cabin in Henderson
4.99 out of 5 average rating, 139 reviews

Cox Cabin “Cabin in the Woods”

Relax in this large, secluded multi-family cabin nestled on the outskirts of Chickasaw State Park on Cagle Trail. 2 King, 1 Queen, 2 Twin beds, Futon and plenty of space for personal air mattress for extra sleeping. Ride in/ride out to miles of trails in Chickasaw State Forest. Very secluded and private cabin with plenty of parking and trailers accessible. Minutes to Chickasaw Golf course, State Park amenities, and Henderson the home of Freed Hardeman Uni. We are pet friendly for a FEE per pet.

Top guest favourite
Flat in Jackson
4.96 out of 5 average rating, 204 reviews

The Waffle House: Historic Full Downtown Apartment

The apartment is called Waffle House because it was the home of Waffle House founder Joe Rogers. The space is a full apartment with kitchen, laundry, living room, bathroom and bedroom with a separate entrance. Located on W Deaderick it’s just a short walk to Restaurants , Farmer's Market, and Hub City Brewing. I am the brewmaster at Hub City Brewing & Rock’n Dough Pizza + Brewery, and my wife works for Hitachi Energy. We live in the downstairs unit so are nearby if there is anything you need.

Top guest favourite
The studio features a comfortable queen size bed covered with a grey quilt and decorative pillows. A small desk with a chair is positioned next to the bed. Warm lighting enhances the cozy atmosphere, while a kitchenette is visible in the background.
Guest house in Henderson
4.95 out of 5 average rating, 544 reviews

Studio Apt on 5th

The Studio on 5th in Henderson, TN is close to Freed-Hardeman University (3/4 mile) & 25 min. from Jackson. This studio w/ 1 queen size bed, 1 bath & kitchenette guesthouse is good for couples & solo adventurers. It is located in a quiet neighborhood next to the host's family home. Includes: Off-street parking, complementary coffee & snacks, Wi-Fi, soaps, shampoo, fresh towels & linens, & outdoor seating. **Simple Check in & Check Out! No "to do" lists!** **Super hosts for over 6 years!**

Top guest favourite
The exterior of the house is displayed, featuring a modern design with an extended roof and large front windows. A stone pathway leads to the entrance, bordered by a landscaped grassy area and scattered trees in the background.
Tiny home in Henderson
4.96 out of 5 average rating, 157 reviews

“The Casita Bonita”

Welcome to “The Casita Bonita” The pretty little house on 130 acres of pure bliss. My wonderful husband Jeremy and I bought 130 acres a few years back and is what we call “our farm” we have had countless picnics and bonfires, Just dreaming of doing something special on our land one day. That is where “The casita bonita” dream came true & it is our pleasure to be able to host guest just like you. I hope you enjoy your stay and the views of our land. Come back to see us soon. Love,Jeremy & Missy

Top guest favourite
Double glass doors framed in a vibrant yellow provide access to the space. A wooden chair complements a dining area adorned with a soft table setting. Exposed brick walls and natural light enhance the warm, welcoming atmosphere.
Home in Finger
5 out of 5 average rating, 149 reviews

La Banque Stylish and comfy stay

Historic bank built in the 1920's restored to it original beauty. Located 5 min from Hwy 45, 8 min from K&M shooting complex and 15 min from Henderson. This is a perfect location for anyone wanting a weekend getaway or a place to rest and reset. Our space reflects peace and quiet, plenty of books to leaf through, a fireplace to warm your feet and a fully stocked kitchen. Spacious bathroom with a beautiful clawfoot tub to soak in. Come get the unique experience of sleeping in bank vault!

Top guest favourite
A close-up image of a Nigerian Dwarf goat features soft brown and black fur. The goat’s bright eyes and gentle expression indicate curiosity. The background consists of blurred greenery, enhancing the goat's presence in its natural environment.
Cabin in Huntingdon
4.98 out of 5 average rating, 229 reviews

Cottage A at Dry Hollow Farm

Local Amish builders constructed this cabin at Dry Hollow Farm in 2021. On 63 acres of woods and pasture we raise Nigerian Dwarf and Alpine goats for milk from which we craft artisan goat milk soap of many varieties. We also raise luffa gourds and organically-grown herbs. We are located five miles outside of Huntingdon, Tennessee, and offer opportunities to interact with our farm animals and shop in our on-farm Soap Shop. We offer a peaceful rural setting with plenty of space to roam.

Top guest favourite
A spacious home is showcased, featuring a combination of stone and brick exterior elements. The entrance is highlighted by large, inviting wooden double doors flanked by greenery. Well-maintained landscaping surrounds the home, complemented by a manicured lawn and the welcoming symmetry of shuttered windows.
Home in Jackson
4.99 out of 5 average rating, 145 reviews

I'm Goin' to Jackson

Clean and cozy home less than 10 minutes from I-40, Union University, and north Jackson shopping, parks, restaurants, and entertainment. Great layout comfortably sleeps up to 8 guests yet cozy enough for 1-2 people. Our family frequents Airbnb properties when we travel and have brought that experience to our home to make it as comfortable as possible. Feel free to use the elliptical or venture outside for a walk or bike ride to see one of two water wheels and ponds in the neighborhood.

Guest favourite
A scenic view captures the entrance to The Farm at Casey Jones Village, framed by a wooden archway. Expansive green fields are dotted with rustic buildings, including a barn and sheds. A well-maintained path leads past vibrant sunflowers and seating areas, inviting relaxation amidst the natural landscape.
Bungalow in Jackson
4.96 out of 5 average rating, 184 reviews

Pearl Cottage in Casey Jones Village

Step back to a gentler time in this pre-civil war shotgun house in the historic Casey Jones Village. A perfect getaway spot for couples for their honeymoon or anniversary or people wanting to get away for a spiritual retreat. Pearl House is complete with a claw foot tub, a huge shower and his and her robes. There are some wonderful books to read at Pearl, many about history and a great collection of cookbooks. It features a complete kitchen, washer and dryer; all the modern amenities.

Top guest favourite
Home in Jackson
4.95 out of 5 average rating, 318 reviews

"Hospitality House"3 br 2 bth house N Jackson TN

You are renting the entire property. 3 bedroom 2 bathroom house with patio. Located in north Jackson close to I 40, restaurants, and shopping. Great quiet Cove neighborhood safe for evening walks. Will accommodate families, traveling nurses, students, or corporate traveler. No pets. Exceptions can be made, contact host. No large parties or events can be hosted. 10 or more pl. Non smoking home smoking in this property will result in $250 cleaning fee Quiet time between 9pm-6am

Superhost
A brick home is presented with a symmetrical façade, featuring a two-car garage and arched windows on either side of the front entrance. Lush greenery and manicured bushes create a welcoming appeal. The driveway leads to a well-maintained lawn with soft grass.
Home in Jackson
4.89 out of 5 average rating, 142 reviews

Are We There Yet? 1 mile from I40/Sleeps 10

Newly renovated 4 bedroom, 2 bath brick home that sleeps 10. Located just a mile from I40. This home is located on a quiet Cove street with a large fenced in back yard. Has a cute closed off sun room for your furry friends, or a nice little reading nook to enjoy your morning coffee. This home is located to everything you may need during your stay. It is 2 miles away from any shopping or dining. Enjoy streaming your favorite shows or movies from 4 smart TVs in the home.

Top guest favourite
A living area features two brown leather sofas adorned with patterned cushions, positioned around a wooden coffee table. A modern kitchen area is visible in the background, with white cabinetry and ample natural light.
Home in Westport
4.99 out of 5 average rating, 188 reviews

The Brandon House, Modern Country Retreat

Forget your worries in this spacious and serene space. Newly renovated home. Conveniently located within 15 minutes of I-40, 1 hour 45 minutes between Nashville and Memphis. Located within 15 minutes of Natchez Trace State Park, Southland Safari and guided Tours, The Dixie Performing Arts Center, Buttrey Wedding and event space, and many other attractions. Hiking, hunting, and fishing close by.

Top guest favourite
A welcoming front porch is shown with two rocking chairs positioned beside potted yellow flowers. A bench sits to the side, and a wooden railing surrounds the porch. Lush greenery is visible in the background, enhancing the peaceful atmosphere.
Home in Jackson
4.97 out of 5 average rating, 249 reviews

Welcome to The Lily Pad!

Keep it simple at this peaceful and centrally-located place. Located just minutes from downtown Jackson, Jackson Madison County General Hospital, The Lift, The Ballpark at Jackson, shopping and restaurants, The Lily Pad is ready for your overnight stop, weekend getaway, work trip or extended stay.

Popular amenities for Jackson holiday rentals

When is the best time to visit Jackson?

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Frequently Asked Questions

  • What are the best places to stay in Jackson?

    Jackson has a range of neighborhoods where visitors can find all types of stays, from residential areas with quieter streets to spots near downtown's venues and restaurants. You might also explore properties around local parks for a relaxed atmosphere.

  • What are the best things to do in Jackson with kids?

    Families in Jackson can explore interactive experiences at local children’s museums, visit animal parks, or enjoy playgrounds and splash pads. Seasonal festivals and community events around the city are also frequently suggested for all ages.

  • What are some of the best things to do in Jackson?

    Jackson has a dynamic music heritage, local museums, and outdoor spaces for walking or picnicking. Many enjoy exploring the city’s historical sites, arts scene, and attending live performances around downtown.

  • How is the weather in Jackson?

    Jackson experiences warm, humid summers around 86–89°F (30–32°C) and mild winters dipping to 29–50°F (-2–10°C). Spring and fall often bring comfortable temperatures, while rain is common throughout the year.

  • When is the best time to visit Jackson?

    Late spring and early fall are frequently suggested, as temperatures are often comfortable and local festivals highlight the community spirit. Summers are warm and lively but bring higher humidity and regular rain.

  • What are the best places to visit in Jackson?

    Jackson has local music museums, historical sites, and a few popular green spaces for outdoor gatherings. Visitors frequently explore the downtown area for art, food, and community events.

  • What are some hiking trails in Jackson?

    You can explore wooded trails at nearby nature preserves or city parks, which feature walking and biking paths suitable for a range of activity levels. These areas are known for their peaceful scenery and opportunities for birdwatching.

  • What are some family activities we can do in Jackson?

    Families in Jackson can visit interactive museums, local parks with play spaces, or animal encounters at nearby nature centers. Community festivals, storytimes, and children’s performances are also often scheduled throughout the year.

  • What are some of the best day trip ideas from Jackson?

    Locals often head to scenic nature reserves, explore neighboring historic towns, or visit lakes and wildlife areas around the region. You might also discover small museums or cultural sites in nearby communities.

  • Are there any pet friendly accommodations available in Jackson?

    Many accommodations in Jackson welcome pets, especially in neighborhoods with access to walking trails or parks. It is common to find pet-friendly options near outdoor areas and in quieter residential parts of the city.

  • What are some local tips for visiting Jackson?

    Local markets and seasonal festivals often reveal Jackson’s community spirit and regional flavors. Exploring downtown on foot and talking with small business owners can lead to insider recommendations and unique experiences.

  • What is Jackson known for?

    Jackson is known for its music history, regional barbecue traditions, and a legacy connected to railroads and industry. The city also has locally rooted arts and a welcoming, community-focused atmosphere.

  • What are the best hidden gems to explore in Jackson?

    Around Jackson, you might find locally owned record shops, murals created by regional artists, or cozy cafés with live music. Less-visited parks and neighborhood art spaces provide a glimpse into the city’s creative side.

  • What are the best foods to try in Jackson?

    Jackson is known for hickory-smoked barbecue, locally made pies, and comfort food such as fried catfish or hot tamales. Regional takes on Southern classics and family-run diners give you a taste of the area’s food culture.

  • What should I bring for a trip to Jackson?

    Bring layers to adjust for warm afternoons and cooler evenings, as well as a light rain jacket, since showers are common year-round. Comfortable shoes work well for exploring museums, parks, and community events.

  • What is the nightlife in Jackson like?

    Jackson’s nightlife is rooted in live music venues, casual bars with local performers, and welcoming spots for late-night southern fare. You may find downtown venues hosting open mic events, jazz nights, or dancing.

  • What are the most popular events or festivals in Jackson?

    Jackson hosts several seasonal events, with music festivals, arts fairs, and regional food celebrations often taking place throughout the year. Celebrations around Labor Day weekend and late spring are among the most popular community gatherings.

  • Are there family friendly vacation rentals in Jackson?

    Visitors to Jackson will find a variety of family-friendly vacation rentals, including options near parks, museums, and quiet residential neighborhoods. Many properties include amenities like kitchens, multiple bedrooms, and access to outdoor play spaces.

Quick stats about holiday rentals in Jackson

  • Total holiday rentals

    Explore 230 holiday rentals in Jackson

  • Nightly prices starting at

    Jackson holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 9,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    220 of Jackson holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Jackson rentals

  • 4.8 Average rating

    Jackson stays are highly rated by guests – averaging 4.8 out of 5!

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  2. United States
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  5. Jackson