Vacation rentals in Winston County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winston County

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

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Guest favorite

Home in Philadelphia

4.95 out of 5 average rating, 183 reviews

The Green Loft in Philadelphia, MS; (# 1)

Once a Man Cave, now your serene escape! This cozy haven features a sprawling island, ample seating, & a 75" flat-screen smart TV with surround sound–perfect for entertaining guests with games or movie nights. With its open-concept layout & soaring vaulted ceilings, the living area exudes a spacious cabin ambiance. Nestled in a peaceful rural community, this one-of-a-kind retreat is bathed in abundant natural light through its expansive front windows, elevating the overall tranquil atmosphere.

Mar 8 – 15

G$30,220 GYD per night

Guest favorite

Townhouse in Starkville

4.92 out of 5 average rating, 232 reviews

Bully's Bullpen on University Drive

New - Bully's Bullpen is simply the perfect location to enjoy your stay in Starkville, long or short. Conveniently located half way between downtown and the MSU campus, this 2 bed, 1.5 bath townhome is the perfect place to land. You can walk everywhere or catch the shuttle just steps away. This completely remodeled townhouse is about 50 yards off University Drive in the heart of the Cotton District with your favorite restaurants and shops minutes away ! Only .4 miles from the MSU Campus!

Jul 31 – Aug 7

G$26,009 GYD per night

Guest favorite

Home in Macon

4.92 out of 5 average rating, 155 reviews

Peaceful Haven - quiet country spot

Our home is a duplex, it is 2 complete houses under one roof. We live in one end, the other ( the rental) has 2 bedrooms, 1 1/2 bath/shower, living/dining room, kitchen, laundry room, closets. Plain and simple but cozy and relaxing. Kitchen with all accessories. Bed linens,bath towels, soap etc are furnished. Front porch: swing and a glider/rocker with west view. Pavilion in yard with picnic table, rocking chairs, small grill, and a fire ring. A country spot that is peaceful, birds singing.

Mar 4 – 11

G$16,973 GYD per night

Guest favorite

Home in Louisville

5.0 out of 5 average rating, 15 reviews

Country Escape -Spacious Comfortable Home

Large mobile home with over 2300 sq ft of space. There is an entertainment room with pool table and log fireplace for the cold nights. Large spacious kitchen for cooking family meals or entertaining guest. There is an eight-seat dining room table in the kitchen. Patio porch for outdoor seating if you want to soak up some southern sun. The home sits on over 2 acres of open land for kids to play or have a nice BBQ. The property is a great place for entertaining inside or outside guest.

Oct 15 – 22

G$43,317 GYD per night

Superhost

Home in Louisville

4.8 out of 5 average rating, 10 reviews

Hannah’s Haven - DesignerTouch

Welcome to our beautiful and stylish two-bedroom, one-bathroom duplex with a full kitchen! This well-lit and airy space has been thoughtfully curated by a designer, featuring contemporary decor that exudes both comfort and sophistication. Whether you're here for business or pleasure, we're confident that our beautiful duplex will exceed your expectations. Book now and treat yourself to a memorable stay in our stylish and well-appointed home away from home. We can't wait to welcome you!

Jul 7 – 14

G$12,273 GYD per night

Guest favorite

Cottage in Starkville

4.98 out of 5 average rating, 202 reviews

StarkVegasBarndo - MSU - 2 Bdrms - NO CLEANING FEE

Our farm guesthouse is perfectly located for games and campus visits. Situated on 20 quiet acres just off of campus. Two bedroom guesthouse inside our beautiful red barn with a kitchenette (refrigerator, coffee maker, sink, and microwave), living room, and bathroom. The guesthouse is 700 sq ft of completely central air-conditioned private space. Front entrance has a covered porch and private entrance. This barn is detached from our farm house sitting about 150ft away. No pets allowed.

May 21 – 28

G$22,850 GYD per night

Guest favorite

Cabin in Louisville

5.0 out of 5 average rating, 50 reviews

Barefoot Cabin

Enjoy privacy at this unique and tranquil getaway. Barefoot Cabin has the feel of being in the country, but it is only a couple of miles from the city limits of Louisville. It is centrally located between Philadelphia and Starkville. So with only a 30-45 minute drive you can enjoy the Neshoba County Fair, casino and water park in Philadelphia, or be at a MSU game in Starkville. It is less than 10 minutes from Lake Tiak-O’ Khata, and only 7 miles from Walmart and Main Street.

Jun 18 – 25

G$19,899 GYD per night

Guest favorite

Chalet in Brooksville

4.99 out of 5 average rating, 377 reviews

Quiet Country Chalet

We are excited to give you the best Airbnb experience. We are in a popular location, yet our driveway is a mile long so it is very quiet and secluded. This is a two story home with 1 queen on the main floor and 1 queen and 2 twins upstairs. There is a grass airstrip right outside the house! Small planes occasionally fly in and out. We ask for a security deposit starting at $200 if you're stars are less then 5. It will be refunded if there's no damage or extra cleaning.

Jul 30 – Aug 6

G$33,311 GYD per night

Guest favorite

Home in Louisville

4.99 out of 5 average rating, 88 reviews

Claude Fair House

Beautiful Home est. in 1916 in the Historic section of downtown Louisville. Kitchen and bathrooms have been updated. Includes an outdoor swimming pool for use in warm weather. Walking distance to main street with shopping, antiques stores, restaurants, library, post office and more. 2.5 miles to Lake Tiakata Resort, 30 miles to MS State , 31 miles to Casinos .NO PARTIES OR EVENTS or NON REGISTERED GUESTS . NO PETS Review House Rules for other details.

Apr 25 – May 2

G$31,641 GYD per night

Guest favorite

Cottage in McCool

5.0 out of 5 average rating, 39 reviews

Cheerful 3-bedroom country cottage

This family friendly relaxing cottage is located 5 minutes away from the Historical District of French Camp. Come enjoy the peacefulness of our cozy home tucked away in the quiet country of Mississippi. It is 36 miles from Starkville MS, ( home of the Mississippi State Bulldogs) 19.5 miles to Kosciusko, and 60 miles from the Pearl River resort, and water park. Located 2.6 miles from the Natchez Trace, approximately halfway between Tupelo and Jackson.

Feb 14 – 21

G$33,250 GYD per night

Guest favorite

Townhouse in Starkville

4.96 out of 5 average rating, 162 reviews

Game Day Townhouse

Perfect space for a game day getaway or just a great time in Starkville! Located in the Highlands Neighborhood of Starkville, just a 5 minutes drive to MSU campus. This townhouse is perfect for a relaxing stay in Starkville. Plenty of parking space and enough room for 4 to sleep- and plenty of space for additional air mattresses. This home is very private and will be perfect for you and your family and friends!

Aug 11 – 18

G$17,292 GYD per night

Guest favorite

Home in Macon

4.97 out of 5 average rating, 123 reviews

The Old Farmhouse (family friendly, easy access)

The Old Farmhouse on the Little Lapp Farm is a family-friendly house with spacious kitchen/dining and living room areas! It's not a 5-star resort by any means, but an old, nostalgic farmhouse with enough renovations to make it a comfy place to stay. 3 bedrooms (1 king, 1 queen, 1 full) and 2 full bathrooms. There's a crib in the master bedroom.

Aug 19 – 26

G$29,426 GYD per night