Holiday rentals in Chickasaw County

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Top-rated holiday rentals in Chickasaw County

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

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Guest favourite

Flat 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 favourite

Home in Amory

5 out of 5 average rating, 204 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 favourite

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 favourite

Guest house in Ecru

4.96 out of 5 average rating, 296 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 favourite

Cottage in Amory

4.98 out of 5 average rating, 132 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).

Guest favourite

Guest house in Tupelo

4.86 out of 5 average rating, 125 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 favourite

Home in Tupelo

4.98 out of 5 average rating, 410 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 favourite

Guest house in Amory

4.99 out of 5 average rating, 139 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

Top guest favourite

Farm stay in Tupelo

4.95 out of 5 average rating, 215 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 favourite

Guest house 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.