Holiday houses in Holly Springs

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Top-rated holiday rentals in Holly Springs

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

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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, 189 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

Superhost
The cottage features a charming exterior with soft pink siding and white shutters accenting two large windows. A welcoming blue door is adorned with a decorative wreath. Brick steps lead to the entrance, surrounded by greenery and a well-maintained lawn.
Home in Holly Springs
4.71 out of 5 average rating, 21 reviews

The Hummingbird Cottage

Come stay in a beautiful cottage located on the grounds of a 1872 stately residence close to downtown Holly Springs, in a quiet historic neighborhood. The cottage sleeps four comfortably with 2 bedrooms, 1 bath. Enjoy a claw foot tub, cozy living room and fully-equipped kitchen & laundry area. Wifi, sunroom, and private back yard. Children and pets allowed. Breakfast items for guest use included. Note: Pets are an additional $25 fee. Prices are for 2 people. Additional are $10/person/night.

Guest favourite
The exterior of the cottage is framed with natural wood and features a screened porch, allowing for views of the surrounding forest. A wooden staircase leads to the entrance, and a stone pathway guides visitors through the lush, green landscape.
Cottage in Coldwater
4.94 out of 5 average rating, 177 reviews

Wynnewood - Odell Cottage

Country get-away! Only 30 Minutes from Downtown Memphis, TN, yet out in the country on a 62 acre estate. Nature trails through the property allow for beautiful, peaceful strolls. We have fishing (in season). **** This cottage is set back in the woods and there is not a TV in this unit but there is Wifi. We have created a serene and unplugged experience. We have the "Wynnewood Elizabeth Cottage" and the "Wynnewood Jettie Jewel cottage" on our property that are listed separately.

Top Guest favourite
A cozy bedroom features a four-poster bed with a white comforter and decorative pillows. Natural light enters through a nearby window adorned with light curtains. A mirrored accent and bedside lamps contribute to the inviting ambiance, while a stylish cowhide rug adds warmth to the wooden floor.
Farm stay in Oxford
4.99 out of 5 average rating, 430 reviews

The Cottage, 2BR Farm Stay by Velvet Ditch Villas

Escape to The Cottage, a charming farmhouse getaway just 8 miles from Oxford. Set on 4 peaceful acres, this cozy retreat blends vintage and shabby chic décor for a warm, inviting vibe. Start your day with fresh eggs, meet our friendly farm animals, and enjoy evenings by the fire pit under stunning starry skies. Perfect for a romantic escape or quiet retreat, The Cottage offers countryside serenity with easy access to Oxford’s dining, shopping, and entertainment. Book your stay today!!!

Top Guest favourite
Guest suite in Collierville
4.95 out of 5 average rating, 247 reviews

Collierville cottage on 3 acre farm

Christmas on the farm has arrived 🎁 Come enjoy our family farm located on 3 acres in the peaceful countryside of Collierville. We welcome guests in separate downstairs guest house with private entrance and porch overlooking pool. Look no further for a nature lovers retreat only minutes from city life. No trains or busy street noises just birds singing and crickets chirping. Amazing restaurants and shopping minutes away when you’re ready to explore! The pool is closed in the winter.

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, 648 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
4.98 out of 5 average rating, 126 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!

Top Guest favourite
The entrance of the vintage home is framed by lush greenery and tall trees. A welcoming American flag hangs from a wrought-iron gate, which leads to a charming courtyard surrounded by a white stucco wall, providing a sense of privacy and tranquility.
Home in Byhalia
5 out of 5 average rating, 24 reviews

White Oak

Stay Where Art, Heart, and History Meet! Charming historic home in the heart of Byhalia, MS. Built in the 1930s and lovingly renovated, this vintage retreat features original hardwood floors, Saltillo tile, unique antique decor, and art by the original owner. Once a beloved family home, now a warm, welcoming getaway full of Southern charm and character. Perfect for relaxing stays, wedding families, work visits or those just exploring North Mississippi and the Memphis area.

Superhost
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, 219 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.

Guest favourite
The exterior of the house is viewed from the front, showcasing a concrete porch bordered by a bed of greenery. Light-colored bricks complement dark blue shutters. A well-maintained lawn extends to the side, filled with trees and shrubs, offering a serene country atmosphere.
Home in Red Banks
4.92 out of 5 average rating, 12 reviews

Dog friendly home with king suite and lake view!

Forget your worries in this spacious and serene space! Just 20 minutes outside of Collierville, TN, you’ll love the quiet, slow pace of this little Mississippi town. This 3 bedroom/2 full bath house sits on two acres of country living! Sit in the spacious living room and look out over the lake across the street! Enjoy a board game or a game of volleyball with friends! You will love the peace and quiet while being just minutes from town!

Top Guest favourite
A modern living area features a light-colored sofa adorned with decorative pillows. Two accent chairs flank a glass coffee table, which holds magazines. Soft lighting is provided by two lamps, while a large artwork of a bull head serves as a focal point above the sofa.
Condo in Oxford
4.93 out of 5 average rating, 381 reviews

Contemporary, The Oxford Retreat, Walk to Games!

The Oxford Retreat – Your Hub for Ole Miss Excitement! Stay in the heart of the action, walking distance to Ole Miss Stadium, Swayze Field, and The Grove. The Oxford Retreat offers modern contemporary décor with mid-century accents. Serene, neutral colors and comfort are at the forefront. Vaught-Hemingway Stadium – 0.9 miles Swayze Field – 0.9 miles Oxford Square – 1.8 miles The perfect spot for game day and relaxation!

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, 197 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

When is the best time to visit Holly Springs?

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Frequently Asked Questions

  • What are the most popular amenities for Hotel Rentals in Holly Springs?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Holly Springs?

    Yes! Work meets play with ease at over 10 vacation rentals in Holly Springs featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do hotel rentals in Holly Springs have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Holly Springs. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Holly Springs have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Holly Springs. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Holly Springs

  • Total holiday rentals

    Explore 30 holiday rentals in Holly Springs

  • Nightly prices starting at

    Holly Springs holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 450 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Holly Springs holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Holly Springs rentals

  • 4.8 Average rating

    Holly Springs stays are highly rated by guests—averaging 4.8 out of 5!