Holiday rentals with outdoor seating in Madison County

4.97 out of 5 average rating, 118 reviews

Cozy Cove Home

Experience the ultimate getaway from the busyness of life! Come stay in our incredible Airbnb located on a serene cove in North Jackson. With plenty of room for the whole family, our spacious living room and kitchen feature comfortable and stylish decor. Unwind at the end of the day with a cozy fire pit on the back deck. You’ll also enjoy the convenience of being near a variety of shopping, restaurants, a hospital, and Union University. Escape the hustle and bustle in our home on the quiet cove.

4.95 out of 5 average rating, 520 reviews

Guesthouse in Henderson

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!**

5 out of 5 average rating, 16 reviews

Home in Medina

Cedar Hill Retreat

Welcome to our newly renovated 2-bedroom, 1-bath Cedar Hill Farmhouse Retreat! Perfectly situated just 5 minutes from charming Downtown Medina, 15 minutes to North Jackson, and 20 minutes to vibrant Midtown. Sleeps 6 in cozy, stylish spaces. Sip your morning coffee on the patio, watch goats and cows graze, listen to songbirds, and unwind by the fire pit under starry skies. Perfect for a weekend escape, family gathering, or local event — soak up peaceful country charm with easy city access.

4.95 out of 5 average rating, 172 reviews

Apartment in Jackson

The Waffle House: Historic Full Downtown Apartment

We call this space the Waffle House because it’s the historic home of Waffle House founder Joe Rogers. The space is a full apartment with kitchen, laundry, living room, bathroom and bedroom. The apartment is located on W Deaderick and is just a short walk to Jackson Walk Restaurants , Farmer's Market, and Hub City Brewing Taproom. I am the brewmaster at the local brewery, and my fiancé works as a reporter for the local newspaper. We live downstairs with our two dogs, Layla and Morri.

4.99 out of 5 average rating, 121 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.

4.96 out of 5 average rating, 171 reviews

Bungalow in Jackson

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.

4.95 out of 5 average rating, 287 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

5 out of 5 average rating, 47 reviews

Daisey’s Homeplace

Daisey’s Homeplace is where we found and rescued our second dog, Daisey, who desperately needed a family to care and love her. We thought it appropriate to name this AirB&B in honor of her. We hope you enjoy this restful, comfy 3 bedroom/2bath home filled with beautiful antiques along with all the amenities you need. It has 4 smart TVs and a little back patio to sit and enjoy. It is located in North Jackson with many restaurants and shopping centers nearby. Come and stay with us!

4.9 out of 5 average rating, 40 reviews

Apartment in Jackson

Little Bird Cottage

This is your unique and tranquil getaway. This artistic apartment is so cozy you will want to never leave. There is something interesting to admire at every turn. Set on 2.5 acres of huge trees it's a a delight to find that it is right in the heart of the midtown Lambuth neighborhood. Less than a 5 minute drive to downtown Jackson for great food, great farmers market, great shopping, and great entertainment! Also, .06 miles to the Jackson Madison Co General Hospital.

4.92 out of 5 average rating, 130 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.

4.96 out of 5 average rating, 48 reviews

The Gettysburg Address

The Gettysburg Address is minutes from Highway 45 and I40. It's located in north Jackson with close proximity to Union University and North Park. With 3 bedrooms, 2 baths and an open floor plan, you'll find that there is plenty of space for you and your family. We have a large backyard for outdoor activities that features a nice seating area with string lights. Our home is also "work friendly" as we have a dedicated workspace with a comfortable chair for your use.