Vacation rentals in Chickasaw County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chickasaw County

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

0 of 0 items showing

1 of 3 pages

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, 177 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, 207 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, 134 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!

Top 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, 300 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

A pathway of stone steps leads from the lush green lawn to the entrance of the rustic carriage house. A wooden swing hangs nearby, providing a place to relax. The exterior features a combination of brick and wood, surrounded by trees.

Cottage in Amory

4.98 out of 5 average rating, 134 reviews

The Nook (on the Tenn-Tom)

Located on the Tenn-Tom River just 1 mile from DownTown, this 500 sq ft upstairs carriage house will relax you with its waterfront view. The exterior is rustic continuing with cottage charm inside. You can relax on the sofa in the comfort of the living room, take a quiet nap in the bedroom or enjoy a game of PacMan. Try grilling with a great water view on the porch or swing. For a change of pace, 2 kayaks & a canoe are for your enjoyment! 🛶 (Twin bed w/trundle downstairs for another guest).

Top guest favorite

A deep front porch is furnished with two wooden chairs positioned on woven rugs. Potted plants are placed on side tables. A welcome mat greets guests at the red front door, while ceiling fans provide cooling for the shaded seating area.

Home in Nettleton

4.99 out of 5 average rating, 81 reviews

Chaney Hill Hideaway

Located on a family farm, your front yard is a pecan grove, your side yard is a hayfield, and your back yard is woods. Sit a spell on the deep front porch (a great place to watch a thunderstorm roll through, or listen to the train whistle off in the distance while enjoying your after dinner drink), or enjoy sitting around the firepit and watching the fireflies dance in the hayfield. Family and (well-behaved) dog friendly. Please read the house rules before requesting a reservation.

Guest favorite

The entryway features a door marked 'Beach House,' leading to a living area with a soft gray couch. A flat-screen TV is mounted on the wall, while natural light enters through a nearby window. Wood paneling adds warmth to the space.

Guesthouse in Tupelo

4.86 out of 5 average rating, 127 reviews

Beach house

Adorable tiny home behind the main house in the backyard; quiet neighborhood in the heart of Tupelo. One bedroom/loft, full bathroom with small kitchen. A Living room with tv. Sip coffee on the porch with breakfast table. Enjoy your evening by the fire pit or on the deck. Many dining and shopping options nearby or take a stroll downtown just 5 minutes away. See Elvis’ birthplace and museum 10 minutes away or enjoy a walk at the park! All within a 10 mile radius!

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, 353 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.

Top guest favorite

A charming wooden cabin is surrounded by tall trees, featuring a welcoming porch with a seating area. Greenery adorns the entrance, while a small path leads to the cabin's front. The natural setting promotes a tranquil and peaceful atmosphere.

Cabin in Eupora

4.96 out of 5 average rating, 26 reviews

Crystal Creek Cabin

Cozy Cabin Retreat in a Peaceful Setting – Perfect for Two Escape to this charming one-bedroom cabin, nestled in a serene and peaceful environment, perfect for a couple’s getaway or a solo retreat. Whether you're seeking a tranquil space to relax or a comfortable base to explore the surrounding area, this cozy cabin has everything you need for a restful stay.

Guest favorite

A serene view of a calm lake is presented, bordered by a grassy area and forested backdrop. Stone steps lead towards the water's edge, with a utility pole visible in the distance. The landscape reflects a peaceful natural setting.

Home in Woodland

4.95 out of 5 average rating, 22 reviews

Lake House

The lake house in Woodland Mississippi is located on a mile and half gravel road, an hour from Tupelo, an hour 15 minutes from Oxford, and 45 minutes from Mississippi State campus (Starkville). This property sits on 30 acre lake, very quiet and peaceful. Fishing is allowed for your stay. You can catch fish, catch a game, and relax with beautiful lake view.

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, 412 reviews

The Tupelo Honey House Historic & Renovated - 2BR

Welcome to the Tupelo Honey Hous - stylish, cozy home in Tupelo—just minutes from downtown, I-22, and Elvis Presley’s Birthplace. Plenty of parking and a calm space to relax after exploring! ✨ Thoughtfully decorated with comfort in mind 🛋 Open living area for relaxing or working remotely ❄️ Climate-controlled for year-round comfort

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, 499 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.