Vacation rentals in Holly Springs

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Top-rated vacation rentals in Holly Springs

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

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Top guest favorite

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, 193 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

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Guest favorite

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

4.81 out of 5 average rating, 36 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.

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Top guest favorite

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, 119 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.

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Guest favorite

A cozy outdoor seating area is illuminated by string lights, featuring a wicker sofa with a blue cushion and a yellow chair. A wood hot tub and a hammock are visible, with views of the surrounding trees beyond the shaded patio.

Home in Byhalia

4.86 out of 5 average rating, 95 reviews

Luxury Pondside Retreat w/Sauna & Hot tub

Escape to 7 private acres of peaceful nature, featuring a King-size bed, private hot tub, and a dedicated sauna room. Living room may be transformed into a home theatre! Just 45 min from Oxford and 40 from Memphis, it’s perfect for a spontaneous couple’s getaway or remote work retreat. With high-speed Wi-Fi, a built-in office, and wildlife all around, you’ll unwind and recharge with ease. Whether it’s a romantic night in or a quiet week off-grid, your luxury country spa escape is waiting.

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Top guest favorite

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

4.97 out of 5 average rating, 37 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 volleyball with friends! You’ll love the peace and quiet while being just minutes from town! Holly Springs-20min Olive Branch-30min Mike Rose Complex-25min

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Top guest favorite

The kitchen features wooden cabinetry and a large countertop with seating for two. Appliances include a black refrigerator and stove set against a backdrop of wood paneling. Soft lighting from overhead fixtures highlights the warm tones of the space.

Farm stay in Olive Branch

4.96 out of 5 average rating, 428 reviews

Horse Farm Hideaway

Industrial farmhouse style meets southern charm on an idyllic horse boarding family farm safely outside of Memphis. Perfect location both for sightseeing in Memphis or bypassing the city entirely. Take a walk among the horses to decompress. Full kitchen and a large bathroom. No exterior windows. Guests sleep well in our quiet and private space. Due to safety concerns, no children under 12. Locals or those without prior positive reviews will be rejected. Our property is smoke free.

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Top guest favorite

Barn in Walnut

5 out of 5 average rating, 15 reviews

Got Milk? Come enjoy your country escape

This building is a former milking barn from the dairy farm that used to be here. Get away from the hustle and bustle and back to nature. spend a relaxing evening on the back porch and enjoy the stars. grab a handful of animal crackers and feed the goats. walk back to the pond and wet a line but watch out for the chickens and ducks that will be free ranging during the day. crack open a few eggs for breakfast from the chickens here, take the rest home if you would like they wont mind.

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Guest favorite

Cottage in New Albany

4.9 out of 5 average rating, 694 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!

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Top guest favorite

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, 167 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!

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Top guest favorite

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, 50 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.

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Guest favorite

Farm stay in Oxford

4.93 out of 5 average rating, 139 reviews

Novel Potting Shed Retreat/Peaceful Bliss

*Quaint & private 2 BR Shed Home *Hi-end bedding *Fully furnished kitchen *Tiled tub/shower w 2 sinks *Laundry pair *Comfy sitting room w elec fireplace *Porch swing on shady veranda *Pet friendly with fenced yard *POOL available just across the driveway. *10 minutes to Campus or The Square *Covered parking *BBQ Grill Enjoy the cozy, countryside lifestyle of this enchanting curated space. Relax in place for meaningful memories. WISHLIST us and Book Now.

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Top guest favorite

Farm stay in Byhalia

5 out of 5 average rating, 13 reviews

Bobwhite's Retreat: An Elevated Countryside Escape

Experience the perfect blend of country charm and modern comfort at Bobwhite's Retreat! Nestled on 5 private acres just outside of Collierville and only 45 minutes from Oxford, this stunning property sleeps up to 10 guests with 2 bedrooms, 2 baths, a full kitchen, and laundry. Enjoy a unique attached gathering space with comfortable seating, cornhole, and games, or relax on the porch while watching deer and taking in peaceful views of nature.

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