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.

Guest favorite

Home in Philadelphia

4.95 out of 5 average rating, 180 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.

Oct 23 – 30

R2,743 ZAR per night
Guest favorite

Home in Macon

4.92 out of 5 average rating, 153 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.

Aug 7 – 14

R1,541 ZAR per night
Guest favorite

Home in Louisville

5.0 out of 5 average rating, 14 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.

Sep 5 – 12

R3,932 ZAR per night

Popular amenities for Winston County vacation rentals

Other great vacation rentals in Winston County

Guest favorite

Home in Louisville

4.88 out of 5 average rating, 26 reviews

5 Bdrm Lovely Southern Home

May 30 – Jun 6

R7,457 ZAR per night
Guest favorite

Home in Macon

4.93 out of 5 average rating, 55 reviews

Macon Memories

Sep 2 – 9

R2,390 ZAR per night
Guest favorite

Tiny home in French Camp

5.0 out of 5 average rating, 18 reviews

Comfy Secluded Getaway

Jul 28 – Aug 4

R1,721 ZAR per night
Guest favorite

Home in Starkville

4.98 out of 5 average rating, 51 reviews

Secluded pet friendly home with screened porch

Jul 23 – 30

R2,401 ZAR per night
Guest favorite

Cabin in Sturgis

5.0 out of 5 average rating, 9 reviews

The Cabin at Arrowhead Ranch

Jul 1 – 8

R3,265 ZAR per night
Guest favorite

Tiny home in Brooksville

4.94 out of 5 average rating, 85 reviews

Hwy 45 Cabin

Jul 15 – 22

R1,093 ZAR per night
Guest favorite

Home in Philadelphia

5.0 out of 5 average rating, 8 reviews

World of Wellness 3

Aug 8 – 15

R2,515 ZAR per night
Guest favorite

Tiny home in Starkville

5.0 out of 5 average rating, 24 reviews

7 Arrows Tiny House

May 20 – 27

R2,585 ZAR per night
Superhost

Home in Starkville

4.97 out of 5 average rating, 30 reviews

Spacious Paradise | Handicap Accessible | Quiet

Feb 27 – Mar 6

R3,298 ZAR per night
Guest favorite

Home in Starkville

5.0 out of 5 average rating, 13 reviews

Brooks Farm Studio - 5 mi (10 minutes) DTN/MSU

Aug 15 – 22

R2,502 ZAR per night
Guest favorite

Apartment in Starkville

4.84 out of 5 average rating, 68 reviews

Studio Just Off Cotton

May 19 – 26

R1,349 ZAR per night
Guest favorite

Home in Philadelphia

4.96 out of 5 average rating, 24 reviews

The Steel House on Poplar

Nov 15 – 22

R3,019 ZAR per night