Vacation rentals in Chickasaw County

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Top-rated vacation rentals in Chickasaw County

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An outdoor pavilion features a spacious grilling area and a large stone countertop. Comfortable seating is arranged around shaded spaces, with a high ceiling supported by wooden beams. Natural light fills the area, providing an inviting atmosphere for gatherings.

Private room in Houston

Trailhead Bike and Bed - Room 1 Handicapped Access

Trailhead Bike and Bed Room #1 is just a few yards from the starting point of the Tanglefoot Trail... Mississippi's premiere 44 mile long bicycle trail. Located just minutes from the square of Houston, this modern facility has all the charm of the small town it is located in. A place where you will find the meaning of southern hospitality, kind people, and a warm welcome. Houston is where the Trail meets the Natchez Trace, one of America's National Parks that is 444 miles of bike friendly roads.

Private room in Houston

Trailhead Bike And Bed - Room 2

Trailhead Bike and Bed Room #2 is just a few yards from the starting point of the Tanglefoot Trail... Mississippi's premiere 44 mile long bicycle trail. Located just minutes from the square of Houston, this modern facility has all the charm of the small town it is located in. A place where you will find the meaning of southern hospitality, kind people, and a warm welcome. Houston is where the Trail meets the Natchez Trace, one of America's National Parks that is 444 miles of bike friendly roads.

The room is furnished with two beds, each adorned with patterned quilts and decorative pillows. A textured area rug lies beneath the beds. A wooden accent wall complements the space, while a bicycle art piece is displayed above the beds. Natural light enters through a window with blinds.

Private room in Houston

Trailhead Bike And Bed - Room 3

Trailhead Bike and Bed Room #3 is just a few yards from the starting point of the Tanglefoot Trail... Mississippi's premiere 44 mile long bicycle trail. Located just minutes from the square of Houston, this modern facility has all the charm of the small town it is located in. A place where you will find the meaning of southern hospitality, kind people, and a warm welcome. Houston is where the Trail meets the Natchez Trace, one of America's National Parks that is 444 miles of bike friendly roads.

Private room in Houston

Trailhead Bike&Bed - All 4 Rooms

Trailhead Bike and Bed is just a few yards from the starting point of the Tanglefoot Trail... Mississippi's premiere 44 mile long bicycle trail. Located minutes from the square of Houston, this facility has all the charm of the small town it's located in. A place where you will find the meaning of southern hospitality, kind people, and a warm welcome. Houston is where the Trail meets the Natchez Trace, one of America's National Parks. This is for the Complete Facility: Kitchen and all 4 rooms.

Guest favorite

A gated entrance welcomes guests with a depiction of a cyclist. A spacious outdoor area is visible, featuring shaded seating arrangements, landscaping, and a performance stage, all surrounded by wooden fencing. The setting is designed for social gatherings and events.

Private room in Houston

5 out of 5 average rating, 6 reviews

Trailhead Bike And Bed - Room 4

Trailhead Bike and Bed Room #4 is just a few yards from the starting point of the Tanglefoot Trail... Mississippi's premiere 44 mile long bicycle trail. Located just minutes from the square of Houston, this modern facility has all the charm of the small town it is located in. A place where you will find the meaning of southern hospitality, kind people, and a warm welcome. Houston is where the Trail meets the Natchez Trace, one of America's National Parks that is 444 miles of bike friendly roads.

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, 137 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!

A comfortable living area features a large beige sofa with decorative cushions, a wooden coffee table, and a flat-screen TV. Soft light enters through two large windows, while a ceiling fan hangs above. A decorative fireplace complements the warm ambiance of the space.

Home in Prairie

4.07 out of 5 average rating, 15 reviews

Relaxing Prairie Home, 29 Mi to Starkville!

The peaceful countrysides of Mississippi await when you book this 3-bedroom, 3-bathroom Prairie vacation rental! This quaint retreat features a cozy living area with a flat-screen TV, a fully equipped kitchen, and in-unit laundry. Spend your time fishing in Weaver Creek Cutoff, golfing at Mossy Oak Golf Club, or shopping and dining in Starkville! For the sports fanatics, visit Starkville Sportsplex or catch a game at Davis Wade Stadium. The choice is yours.

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

4.96 out of 5 average rating, 24 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.

An open living space features a king-sized bed with crisp white linens visible in the background. A dark leather couch with decorative pillows sits across from a wooden coffee table. A small desk and light fixture are also present, enhancing the functional layout.

Apartment in Houston

4.75 out of 5 average rating, 4 reviews

Hilltop Retreat

Enjoy a quiet stay with a view of a pond that's just half a mile from Houston's courthouse square. Newly renovated with a kitchenette (including a fridge and a microwave with advanced features like air frying) and king sized bed plus a couch and a fireplace for cool nights.

Private room in Houston

Bridges-Hall 1st Floor Queen

Enjoy your stay in our quaint home built in 1884 and join us for a southern-style breakfast. Our queen flex space is just inside the main entry to the home and features a Murphy bed. Don't worry; we have memory foam and a mattress topper that are super comfortable!

Guest favorite

A living area features two comfortable sofas surrounding a wooden coffee table. A vintage-style cabinet is set against the wall, and a television is mounted above it. Deer mounts add a rustic touch to the wood-paneled walls, enhancing the cabin's character.

Cabin in New Houlka

4.96 out of 5 average rating, 112 reviews

Deer Camp

This cabin is located 1/4 mile from the Tanglefoot Trail. There are two grills at the cabin. A fishing pond is located behind the cabin. Air mattresses are in the laundry room for additional guests. Feel free to use condiments or anything else in the refrigerator.

Private room in Houston

Bridges-Hall Full Studio 1

Enjoy your stay in our quaint home built in 1884 and join us for a Southern-style breakfast. This room is compact if you're planning a quick stay and features a private bath and full-size bed.