Holiday rentals in Holly Springs

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Top-rated holiday rentals in Holly Springs

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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, 162 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
A charming brick cottage with a steeply pitched roof is framed by trees and shrubs. A stone pathway leads to the front door, bordered by a well-kept lawn. Two rocking chairs are positioned on the front porch, inviting relaxation.
Home in Holly Springs
4.91 out of 5 average rating, 191 reviews

The Butterfly Cottage

The Butterfly Cottage is a lovely 1920’s English cottage in the historic district of Holly Springs, MS. Located 1 block off historic downtown square. Desirable area of town. Walking distance to restaurants, coffee shop, boutique, antique stores, museum, art gallery and library. Very historic town. Located on a large, treed lot. Gorgeous backyard with sitting area . Full kitchen, laundry facilities. This house is on Hwy 7, just 1 mile away from I22. Easy drive to Oxford, Memphis, Collierville

Top guest favourite
A comfortable seating area features a brown sofa facing a rustic wooden coffee table, placed on a patterned area rug. The walls are accented with warm wood panels and metallic trim. A TV is mounted on the wall, and curtains frame the window.
Cabin in Ripley
4.97 out of 5 average rating, 102 reviews

The Outskirts

Take a break and unwind at this peaceful oasis. Quiet country studio cabin located on the outskirts of Ripley. Conveniently located 5 miles from The Red Barn event venue, 8 miles from Ripley's First Monday Flea Market and 15 miles from Blue Mountain Christian College. Only minutes away from Bennet Lake Hunting club and Dumas Lake. For dining: Enjoy a delicious meal at Simmer on Down Steak house 3.5 miles away. For Essentials: Dollar General and Clarks Country Store are only 3 miles away.

Top guest favourite
A charming guest house is framed by lush greenery and a well-maintained lawn. The wooden structure showcases a screened porch with red accents, along with a welcoming American flag. An outdoor seating area is visible, inviting relaxation in a tranquil environment.
Guest house in Como
4.98 out of 5 average rating, 161 reviews

Heavens Trees: Small town Guest House

Cute comfortable guest house in small Mississippi town. Como is 40 miles south of Memphis and 40 miles from Oxford , MS. Take in a Ole Miss game or check out Beale St. We are within walking distance of Main Street in Como where you can find great restaurants and antiques. Coffee, tea and continental breakfast with snacks and bottled water provided. Swim in our lovely pool, sip your morning coffee sitting on the screened in porch overlooking the pool and pasture with 4 mini horses.

Top guest favourite
A living room features a dark blue couch adorned with decorative pillows, positioned near large windows dressed with light curtains. A coffee table sits centrally, displaying a stack of books and small plants. Wall sconces and a mirror add to the room's inviting ambiance.
Cottage in New Albany
4.9 out of 5 average rating, 662 reviews

The Cottage in Downtown New Albany, MS

Come and enjoy The Cottage in Downtown New Albany, MS! This newly renovated property boasts detailed interiors and modern luxuries, while still maintaining the cozy comforts of a weekend cottage. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

Top guest favourite
The exterior of a newly renovated home features a charming front porch supported by decorative columns. Large windows allow natural light to illuminate the space, while a well-maintained lawn and neatly arranged shrubs enhance the welcoming entryway.
Home in New Albany
4.99 out of 5 average rating, 141 reviews

The Queen on Cleveland

Come and enjoy The Queen on Cleveland in Downtown New Albany, MS! This new AirBNB is a sister property to “The Cottage”. This newly renovated home boasts detailed interiors and modern luxuries. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

Guest favourite
A wooden sign reading 'SUNSET' is positioned above a gravel pathway leading to a welcoming country home, surrounded by trees. The inviting entrance opens to a lush green landscape with floral accents and unobstructed views of the fields beyond.
Home in Crawfordsville
4.94 out of 5 average rating, 216 reviews

Sunset Ittelegna

Take it easy at this unique and tranquil getaway. Secluded, country home with lush gardens and saltwater pool. Sunset Ittelegna is just 20 minutes from Memphis, TN. Fully functioning mini kitchen and separate living space. There is a private drive dedicated to the freestanding home.You’ll enjoy sweeping views of the Delta and most breathtaking sunsets through a wall of floor to ceiling windows.Sunset Ittelegna offers privacy and comfort. Perfect for your getaway.

Top guest favourite
The tiny house features a rustic wooden exterior with a red metal roof. Soft ambient lights are strung around the door area, which is framed by greenery and flower beds. Outdoor seating is provided by two white chairs on a gravel patio, creating a welcoming space.
Tiny home in Olive Branch
4.98 out of 5 average rating, 146 reviews

The Pony

-Boasting a small hoofprint of 128 square feet with a loft. Ideally situated in a safe area for those visiting/passing through Memphis. -Tranquil views of open fields, horses, and a variety of other furry friends at a working horse boarding barn. -Stay solo or with someone you don't mind cozying up to. Ideal for mobile guests comfortable with stairs and tighter spaces. Locals or those without positive reviews will be rejected. Our property is non smoking.

Guest favourite
The exterior of the home is presented, featuring a welcoming entrance with a star motif. Two chairs are situated on the porch, and greenery surrounds the area, creating a comfortable environment for guests and pets. Natural light filters through the windows, enhancing the inviting facade.
Home in Holly Springs
4.83 out of 5 average rating, 225 reviews

Gallop-Inn Bungalow

PETS are welcome but please no more than 2 pets. Super easy self check in with keypad. Great location just outside the city and just a short drive to Historic Downtown Collierville, TN or how about a 30 minute drive to Downtown Memphis/Beale Street, Tunica Casinos, and Graceland. Plenty of Acreage for your pets to exercise. Enjoy the local sights of the area like Pickwick Lake and State Park less than an hour drive. Enjoy all the conveniences of home.

Top guest favourite
A spacious studio apartment features a queen-sized bed with a blue and white patterned quilt, complemented by decorative pillows. A dual recliner loveseat and writing desk are included. Tall windows allow natural light to fill the room, while a private entrance is visible in the background.
Guest suite in Oxford
4.93 out of 5 average rating, 270 reviews

Spacious Oxford Retreat - Large Yard

Spacious studio apartment with 10 ft ceilings and tall windows make it bright and airy. Located in a quiet, wooded neighborhood just a 10 minute drive from campus or the Square. Queen-sized bed, dual recliner loveseat, writing desk, bar top dining table, washer/dryer unit, and kitchen with full size refrigerator, microwave, and stovetop. Private outdoor patio that is fenced-in. Personalized door lock code for added security. Roku TV and free WiFi.

Guest favourite
A modern southern-style house is presented with a black exterior and a charming front porch. Large windows enhance the façade, allowing natural light to fill the interior. Lush green grass and trees surround the property, contributing to a serene atmosphere.
Home in Red Banks
4.94 out of 5 average rating, 36 reviews

The Water's Edge

Welcome to the Water’s Edge House, where modern design meets southern charm and comfort. It's not just a house, it's a lifestyle. This stunning southern style, 3-bedroom house offers the perfect blend of modern design and comfortable living. Nestled in a serene neighborhood, this home is ideal for families, professionals, or anyone looking for a spacious and stylish living space.

Top guest favourite
The sleeping area features a queen bed with a rustic quilt, accented by supporting wooden nightstands and a bench at the foot. Warm wood paneling and a decorative star motif are visible on the floor, enhancing the cozy barn atmosphere.
Barn in Pocahontas
4.99 out of 5 average rating, 208 reviews

The Bedroom in the Barn

Welcome to Smith’s Farm Horseshoe Haven. A wonderful place to step back to the times of days gone by, where life is a little slower and simpler and enjoy a stay in our rare little gem "The Bedroom in the Barn" Lose yourself in the country, unwind and smell the fresh air and listen to the sounds of horses around you. A sweet experience you won't forget!

Popular amenities for Holly Springs holiday rentals