
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.

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.

“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

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!**

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.

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.

"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

Peaceful Sears, Roebuck and Co. Mail Order Home.
Come and stay at a freshly remodeled cozy home built in the 1940’s. The home has two bedrooms with living room with pull out couch, a galley style kitchen, dining room and bathroom with large walk in glass shower and soaker tub. Two Smart 55” TV’s in the home and WiFi access for your work. We are centrally located to Freed Hardeman University and downtown Henderson. Only 20 minutes from Jackson. Follow us @kenzley holdings

Swan House
This two bedroom, newly renovated 1950’s home exhibits historic midtown charm paired with modern style. Our quiet, dead-end street offers the space to get away, while being conveniently located ½ a mile from the Hospital and right around the corner from the local shops and restaurants of downtown Jackson. Two minutes from the bypass for a quick drive up north; ten minutes from Union University.

The Tinker Retreat
Enjoy all the things Jackson has to offer within minutes of this home. Whether your looking for a good nights rest or a fun family game night, The Tinker Retreat is ready to accommodate. Step inside, leave your troubles at the door and relax in our massage chair or catch a game of foosball while enjoying some freshly popped popcorn. This home offers something for everyone to enjoy!

Ceiling 163
Loft 163 is located on the Court Square in Downtown Huntingdon TN. It's on the second level of a newly renovated historic building that dates back to the late 1800's. It has amazing views and is in walking distance to The Dixie Performing Art's Theatre, Court Theatre, restaurants, coffee shop, gift shops, and more.

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.

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
Other great holiday rentals in Jackson

Cutting Edge Family Apartment.

35 Min from BOC!

Pool House in Midtown - Centrally Located

The Gettysburg Address

The Roland Suite

Jackson Sweet Retreat

Mid-Century Modern Gem 1 mile from Jackson General

Holiday In Holladay at “The Station”
When is the best time to visit Jackson?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $159 SGD | $161 SGD | $158 SGD | $161 SGD | $154 SGD | $158 SGD | $154 SGD | $154 SGD | $155 SGD | $172 SGD | $170 SGD | $167 SGD |
| Avg. temp | 4°C | 6°C | 11°C | 16°C | 20°C | 24°C | 26°C | 25°C | 22°C | 16°C | 10°C | 6°C |
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 house rentals in Jackson have air conditioning?
Absolutely! We offer over 160 house rentals with air conditioning in Jackson. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Jackson?
Experience the best of Jackson with our house rentals, starting at about $30 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 apartment rentals in Jackson?
Jackson has more than 10 family-friendly apartment 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 220 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 8,690 verified reviews to help you choose

Family-friendly holiday rentals
140 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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