Vacation rentals in Chickasaw County

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Top-rated vacation rentals in Chickasaw County

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Guest favorite

The bedroom features a spacious bed adorned with a soft gray coverlet and an array of decorative pillows. Light-colored curtains frame a window, allowing natural light to illuminate the room. Two bedside lamps provide additional lighting, and a comfortable bench is positioned at the foot of the bed.

Apartment in Calhoun City

4.93 out of 5 average rating, 176 reviews

Comfortable and stylish one bedroom apartment.

We are excited to host you and a loved one (max. of 2 guests) at our 2nd floor (stairs), 1 bedroom/1 bath short-term rental full of character. In this apartment, you will have exclusive access to a spacious, private bedroom and a large, full bathroom and kitchen. If you're looking for a tastefully decorated space with a modern feel but with the ambiance of something historic, we're the perfect spot. Guests aren’t allowed to host “company”. Only reg. guests Read full listing before booking.

Top guest favorite

A screened porch offers a relaxed seating area with comfortable chairs and a dining table dressed in a red and white checkered tablecloth. Views of the lake and surrounding greenery are visible through the screens, enhancing the connection to the outdoor setting.

Home in Amory

5 out of 5 average rating, 199 reviews

Riverside Escape at Sunset Point

Relax in clean comfort on Aberdeen Lake and the Tenn-Tom Waterway. Whether fishing in warm months or just watching the geese and ducks in the winter, it is quiet and cozy. It has a large screened porch, electric fireplace, pier, shady fenced yard, rockers, a swing, fire pit, gas and charcoal grills. The kitchen is well equipped and the home is handicap accessible with a porch lift, grab bars and ramps. Columbus (16 mi), Tupelo (38 mi), MSU/Starkville(45 mi) & River Birch Golf Course (10mi)

Guest favorite

A country house is surrounded by lush green grass and mature trees, offering shade and a serene setting. Colorful flowering shrubs are positioned in front of the home, enhancing the natural landscape.

Home in Okolona

4.96 out of 5 average rating, 130 reviews

Grandpa’s Farm House

Perfect house for anyone looking to relax in the country for a bit! This home is on a seventy acre catfish farm.🏡 Conveniently located 3 miles off the Alternate 45 HWY, halfway between Tupelo and West Point.🌟see the stars at night!🌟skip the hustle,bustle,and noise of city life... Just twenty minutes from the Natchez Trace parkway, 25 minutes from Tupelo, Starkville is 45 minutes away.Gulf Shores is close to 5 hours from us..an overnight stop on your way to the beach!:)..Come ...stay with us!

Guest favorite

A cozy outdoor area features a circular stone fire pit surrounded by four comfortable chairs. A small sign indicating parking is visible in the foreground, with a quaint cottage set among lush greenery in the background.

Guesthouse in Ecru

4.96 out of 5 average rating, 291 reviews

The Doughboys Cottage

Private full bath Queen Bed Cottage near Natchez Trace Park & Mississippi's premier biking destination, Tanglefoot Trail. Perfect for single or double occupancy. 25 miles from Elvis Presley Birthplace 35 miles from The University of Mississippi and Rowan Oak, the home of William Faulkner. Enjoy a fresh pan of The Doughboys Fresh Baked Cinnamon Sticky Buns $13.00. Delivered to your door in a.m. Local venues: Great Mexican Restaurant 2 miles Walmart 3 Miles Convenient Store 1/4 mile

Top guest favorite

The exterior of a historic home features a covered porch with American flag accents. Potted ferns hang from the ceiling, flanking two chairs and a small table. A stone walkway leads to the entrance, surrounded by landscaped greenery and blooming flowers.

Home in Tupelo

4.97 out of 5 average rating, 343 reviews

Historic Charm Near Downtown Tupelo

Newly remodeled historic home less than a mile from Downtown Tupelo where you can enjoy shopping and plenty of tasty restaurants. The house has been thoughtfully furnished in a fun, midcentury modern style. The beds are very comfortable and the master bathroom has a giant shower and separate soaking tub to enjoy after a long day. Please note the house is close to the famous downtown train so you may hear the engine horn at night.

Guest favorite

A cottage with dark blue siding is framed by neatly trimmed bushes and green grass. A covered porch features a bench alongside the main entrance, while tall trees provide shade in the background. A gravel driveway leads up to the home, adding to its inviting curb appeal.

Cottage in Tupelo

4.91 out of 5 average rating, 205 reviews

Cozy Tupelo Getaway | Dog Friendly | Near Downtown

Relax in this cozy, dog-friendly retreat near Elvis’ Birthplace and downtown Tupelo. Perfect for road trips, remote work, or extended stays with fast WiFi, comfy beds, and a quiet neighborhood. Enjoy peaceful mornings, evening cocktails under string lights, and easy access to I-22, Oxford, and Starkville. Superhost care, self check-in, and all the comforts of home await you and your pup.

Top guest favorite

The exterior of a renovated house is displayed, featuring a welcoming front porch with wooden steps. Lush trees surround the property, enhancing the tranquil setting. A gravel pathway leads from the porch to the yard, where a patch of grass complements the natural surroundings.

Home in Tupelo

4.98 out of 5 average rating, 405 reviews

The Tupelo Honey House Historic & Renovated - 2BR

Enjoy a stylish and comfortable experience located in Tupelo, MS. Whether you’re here for work or just for fun, our hope is that you can kick back and relax in this calm space. We are just minutes from I-22, the birthplace of Elvis and downtown Tupelo. There is plenty of parking at the Tupelo Honey House too. We love Tupelo and are happy to answer any questions.

Top guest favorite

The exterior of the guest home addition is shown, featuring a neatly landscaped garden with shrubs and flowers. The driveway is paved, leading up to a garage on the right. Large, arched windows enhance the facade, allowing natural light to enter the rooms.

Guesthouse in Amory

4.99 out of 5 average rating, 137 reviews

Honey Pot

I think you will enjoy staying at our beautiful guest home addition on Riverbirch golf course. You can walk or run in our safe neighborhood or bring your clubs for an evening of golf. Pets may be allowed for a small additional fee - Please discuss with me prior to your booking. I enjoy social media and provide high speed internet

Guest favorite

An open-concept living and dining area is showcased, featuring a spacious seating area with a light-colored couch. A dining table with seating for multiple guests is positioned near the kitchen, which includes modern appliances. A flat-screen TV is mounted on the wall, complemented by warm lighting.

Farm stay in Tupelo

4.95 out of 5 average rating, 210 reviews

The Apiary

Our private homestead is the perfect setting for your getaway. You’ll have the best of both worlds—with 20 acres of privacy with all the excitement of Tupelo just miles away. While here, you can relax in the serene outdoors while watching our farm animals graze. You can also gather eggs and enjoy them for breakfast!

Top guest favorite

A fenced entrance is framed by brick pillars and a wrought iron gate. Beyond the gate, a gravel pathway leads to a private outdoor area with seating, flowering plants, and a small fountain. Lush greenery surrounds the space, providing a sense of privacy.

Guesthouse in Tupelo

4.99 out of 5 average rating, 497 reviews

Cozy Guest House in Downtown Tupelo

Private cozy one bedroom with a bathroom guesthouse available. It is conveniently located in downtown Tupelo. Private entrance and includes wifi, roku tv, microwave, mini fridge, and Keurig coffee maker. Within walking distance to downtown Tupelo with great Restaurants.