Holiday rentals in Simpson County

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Top-rated holiday rentals in Simpson County

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

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Guest favourite

A spacious bedroom is furnished with a large bed adorned with a patterned blue and white duvet. Natural light enters through two windows, framed by sheer curtains. A wooden dresser is positioned against one wall, complemented by a standing lamp and small nightstand.

Home in Harrisville

4.96 out of 5 average rating, 52 reviews

Country Retreat

Relax with the whole family at this peaceful place to stay. We offer 45 acres of woods with accessible trails, a perfect get away from the city life. Very beautifull and remote country setting and yet close enough to nearly restuarants, convenient stores and gas station. Spacious three- bedroom two-bathroom with fully equipped kitchen and laundry room. Bring your favorite fishing rods to fish in our pond for bass or bream or take a walk in the woods. Our chickens are ducks are people friendly.

A spacious kitchen is highlighted by wooden paneling and a distinctive center island with a white countertop. Light filters through large windows, and a green wall adorned with decorative elements adds a touch of nature. Modern appliances and dining seating complete the inviting space.

Cabin in Mendenhall

4.81 out of 5 average rating, 21 reviews

Cozy Cabin w/ Hot Tub & Wi-Fi

Welcome to your peaceful escape in the heart of Mississippi — where cozy comfort meets modern convenience. This charming cabin is perfect for family getaways, romantic weekends, wedding guests, or long-term stays. Soak under the stars in your private hot tub, stream your favorite shows with fast Wi-Fi, and wake up to the sounds of nature — not traffic. With open space for the kids to play, a fully stocked kitchen, and thoughtful touches throughout, this cabin makes it easy to feel at home.

Top guest favourite

A wooden staircase leads to a treehouse entrance, surrounded by lush ferns and tall trees. A welcome mat with a cheerful message is positioned at the base of the steps, and a sign labeled 'Owl Nest' is visible next to the door.

Treehouse in Mount Olive

4.99 out of 5 average rating, 127 reviews

A True Treehouse- Owls Nest @Pines and Pillows

Escape to our enchanting treehouse experience nestled in the heart of Mississippi's countryside. Experience rustic vibes among the treetops with cozy accommodations, breathtaking views, and comforting amenities. Perfect for romantic getaways or adventurous retreats, our unique rental offers a serene escape with a touch of whimsical charm. Book your stay now for an unforgettable experience in nature's embrace.

Guest favourite

Home in Magee

5 out of 5 average rating, 5 reviews

Raywood Manor

Enjoy this spacious home on 5 acres, featuring two inviting living rooms, a large family room, and plenty of comfortable spaces to relax and sleep. Have fun with the pool table and foosball table, or unwind on the full walk-around deck overlooking the fenced backyard. Located right in the middle of town, you’re within walking distance to Walmart while still enjoying peaceful, open surroundings.

A well-designed kitchen features wood paneling and a spacious island with a white marble countertop. Natural light fills the room through large windows. A green plant wall adds a touch of nature, while wooden dining chairs surround the island, creating a welcoming space for gatherings.

Cabin in Mendenhall

4.54 out of 5 average rating, 82 reviews

Hot Tub Vibes* Unlimited Wi-Fi *Rustic Cabin Reset

Escape to a cozy cabin in Mendenhall, MS with a hot tub & fireplace! Perfect for couples, families, and last-minute getaways. Fast WiFi + kitchen for extended stays. Weddings must be pre-approved — contact host for pricing & approval!