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Holiday rentals in Jackson

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Top-rated holiday rentals in Jackson

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Flat in Jackson
4.96 out of 5 average rating, 198 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.

Guest favourite
Home in Jackson
4.95 out of 5 average rating, 21 reviews

2bedroom-midtown house-The Nest on Swan

Welcome to your cozy 1950s house in the heart of Jackson, TN! This charming two-bedroom, one-bathroom home is tucked away on a peaceful dead-end street, offering the perfect balance of privacy and convenience. Centrally located, you're just minutes from dining, shopping, downtown, and the hospital. Hop on the 45 Bypass to head to northside Jackson, just 3 miles away. Whether you're here to explore the town or simply relax, our comfortable space provides all the essentials for a memorable stay.

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, 149 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
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, 541 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!**

Guest favourite
A modern living room is presented with a spacious gray sofa facing a wood coffee table. A decorative armchair features a blue and white pattern. The open layout leads to a dining area with ample natural light, while a ceiling fan provides a cool breeze.
Home in Jackson
4.91 out of 5 average rating, 22 reviews

New NW Jackson home w/ foosball!

Welcome to your brand-new modern retreat! This spacious 3 bedroom, 2 bath home is the perfect getaway for families or groups. Enjoy gathering in the dedicated dining room, ideal for meals or can be used as a dedicated workspace. Unleash your competitive spirit with a game of foosball, or head outside to our private patio and fire up the grill for a fun time. With all new construction, you'll experience comfort and style throughout. Located just 8 minutes from Union University and restaurants.

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, 148 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!

Guest favourite
A single-story home features a well-maintained exterior with light-colored siding and a neatly trimmed lawn. The attached garage has space for vehicles, while a decorative element is placed near the entrance. The inviting front yard is shaded by mature trees against a clear blue sky.
Home in Jackson
4.9 out of 5 average rating, 67 reviews

Cozy Modern Minilmalist Stay in North Jackson

Welcome to your perfect getaway in the peaceful northernmost part of Jackson, Tennessee. Our cozy and comfortable home is ideal for families, solo travelers, or business guests seeking a serene retreat with easy access to everything Jackson has to offer. This inviting space features 3 bedrooms, 2 bathrooms, Wi-Fi, smart TV and an array of kitchen utilities. Whether you’re here for a short stay or an extended visit, you’ll find everything you need for a comfortable and relaxing experience.

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, 143 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, 183 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.

Guest favourite
Home in Jackson
4.95 out of 5 average rating, 315 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

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, 230 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.

Guest favourite
A comfortable living area features two spacious sofas and a cozy armchair, arranged around a decorative area rug. Soft lighting is provided by table lamps on either side. A large wall mirror reflects the space, while a piece of artwork adds a touch of color.
Townhouse in Jackson
4.94 out of 5 average rating, 105 reviews

Our Little Tinker!

Our Little Tinker is unique, spacious, cozy and more importantly close to retail shopping, fast food, restaurants, event centers, about a mile off the interstate and more. 2 spacious bedrooms with queen beds and 1 full bath.

Popular amenities for Jackson holiday rentals

When is the best time to visit Jackson?

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Frequently Asked Questions

  • Where should I stay in Jackson?

    Make yourself at home in Jackson by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in Hicksville, over 190 vacation rentals in Lawrence, and over 100 vacation rentals in Gilmore.

  • Are there vacation rentals with a dedicated workspace in Jackson?

    Yes! Work meets play with ease at over 120 vacation rentals in Jackson featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Jackson?

    Four-legged friends are welcome in Jackson. Choose from more than 80 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Jackson have air conditioning?

    Absolutely! We offer over 30 apartment rentals with air conditioning in Jackson. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Jackson?

    Experience the best of Jackson with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Jackson have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Jackson. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Jackson?

    Jackson has more than 130 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Jackson have wifi?

    Absolutely! We offer over 160 house rentals with wifi in Jackson. Enjoy a tailored experience with all the comforts you desire.

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 $38 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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  4. Madison County
  5. Jackson