Holiday rentals in Prentiss

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Top-rated holiday rentals in Prentiss

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Superhost
A bright living area features two white armchairs draped with colorful throws. A small table holds a vase of flowers, while sunlight filters through sheer white curtains, highlighting the deep blue walls. A wooden console table adds warmth to the inviting space.
Home in Monticello
4.75 out of 5 average rating, 88 reviews

Diva Farm House Escape

Are you looking to get away from the fastness of big city life? Want to enjoy time outdoors? Are you wanting to take a second to slow down and feel immersed in Southern culture? Are you a lover of local boutiques and Mom & Pop Shops? Well then, look no further. The Diva Farm House is nestled away in a quiet neighborhood, and is surrounded by very little traffic. The house is covered from top to bottom with knotty pine to really give you that farmhouse / cabin feel! Monticello is known for charm!

Top guest favourite
The historic farmhouse features a light grey exterior with a spacious front porch, supported by white columns. Two American flags are displayed. Lush green landscaping surrounds the home, offering a welcoming entrance. A gravel driveway leads to the house, setting a tranquil, inviting scene.
Home in Sumrall
5 out of 5 average rating, 17 reviews

Historic home, Walk-bike trail, Porches & Fire pit

Historic farmhouse within walking distance of the Longleaf Trace biking trail, local restaurants and boutiques. The home has original features from 1906, a favorite is the claw foot tub, take a relaxing bath! Have coffee on the front porch swing! Enjoy the back yard barbequing on the grill or make smores on the firepit! Conveniently located 2 blocks f/ the Longleaf Trace, 2 miles f/ Sumrall Sportsplex public use tennis and pickleball courts, 2 miles f/ Dogwood Venue, & 15 miles f/ USM Campus.

Top guest favourite
An open living area features a large wooden table at the center, surrounded by antique chairs, with a decorative rug underneath. A mix of seating options, including a green couch and a brown vintage sofa, is arranged around the space. Natural light enters through window blinds.
Home in Columbia
4.97 out of 5 average rating, 144 reviews

Herstory Home B&B- Downtown Columbia

Enjoy a stylish experience at this centrally-located cottage in downtown Columbia. Each guest gets to experience 1 free food and latte item per day at Coffee-Haus… the best Coffee experience in the Pine Belt! Come relax in our amazing soaking tub, or steam it up in our very roomie shower for two. Whether you are on a business trip and need super high speed internet and a peaceful nights sleep, or you want to celebrate with your family, the Herstory Home is excited to host your stay in Columbia!

Top guest favourite
An aerial view displays the 30-acre Christmas tree farm covered in neatly planted conifer trees. Various buildings, including a large covered area and open warehouse space, are visible alongside the expansive green fields, highlighting the farm's vibrant landscape.
Farm stay in Hattiesburg
4.95 out of 5 average rating, 106 reviews

Cozy FarmHouse w Goats & GlassBlowing 5min to town

Located on Thomley’s Christmas Tree Farm, home to the only Glassblowing Hot Shop in Mississippi. Featured on HGTV’s “Hometown”, we welcome fans of the show. The house is 2,600sqft. New granite countertops and Wifi. We have 28 goats & 19 baby goats. Kidding season is Feb-Mar. Tree Farm is busy from Nov 15- Dec 15. The GlassBlowing studio is seasonal and stays busy Feb-April & Oct-Dec. We also have a nice Gallery. Thomley Farmers Market is the Last Saturday of the month 10am-2pm from April-August

Top guest favourite
A charming single-story home is nestled among tall trees and colorful flowering shrubs. The front porch features seating options, while a sloped green roof complements the white exterior. A gravel path leads to the house, offering a sense of tranquility in a natural setting.
Home in Sumrall
4.99 out of 5 average rating, 67 reviews

Mill Creek Farm

Relax in quiet peacefulness surrounded by forest. You really notice the beauty and sounds of nature here. Walk down the trail to the one acre pond to feed the fish from the pier. Or walk out the back door to another trail to experience complete solitude. This was my grandparent's home where they once farmed 80 acres. It's cozy, quaint and very private. However, it's less than four miles from downtown Sumrall and 16 miles to Hattiesburg. Your pets will enjoy the large fenced in back yard.

Guest favourite
Cabin in Tylertown
4.91 out of 5 average rating, 22 reviews

Modern Cabin with Balcony Private Country Setting

Modern meets rustic in our brand-new, three-bedroom, two-bathroom cabin with all the comforts of home. This two-story cabin was a family project from the ground up, completed in 2025. We enjoyed designing this guest house and hope you find it a rejuvenating space. The cabin is great for a refreshing weekend getaway, a home base for a work crew or home-away-from home while visiting friends in the area. Private location away from the road but less than ten minute drive to Tylertown.

Top guest favourite
Two wooden Adirondack chairs are placed beside a small side table on a wooden porch. A potted plant rests on the table, which also holds two mugs. A window is visible in the background, offering a view of the surrounding trees.
Tiny home in Collins
5 out of 5 average rating, 106 reviews

Tiny home tucked in the woods

You will find yourself nestled in the heart of the woods and our charming tiny home offers a peaceful retreat from everyday life. *Located 9 minutes from Taylorsville, 12 minutes from Collins, 24 minutes from Laurel 45 minutes from Hattisburg, Ms. Surrounded by towering trees this home features a warm, inviting interior with rustic touches and modern amenities in a quiet location. Sit down on the front porch with a cup of coffee and enjoy a moment of rest & relaxation.

Top guest favourite
A serene pond surrounded by tall pine trees is featured, with a canoe resting on the grassy bank. A small wooden bench sits nearby, providing a spot to enjoy the tranquil view. The natural setting is enhanced by scattered dry leaves on the ground.
Cabin in Prentiss
4.95 out of 5 average rating, 58 reviews

Escape to the country with your pets!

Need a break? A place to meet up with family/friends? A romantic getaway? This comfy cabin can accommodate! Kick back & relax in the rustic-chic space. Full kitchen, 2 bedrooms, 2 bath, living room, dining area. Enjoy the view of the pond from your porch, put a line in or walk an easy trail. Traveling with a your furry friends, no problem-all are welcome. Close to Longleaf Trace, Rt 84, state parks. Ride the trace, we will pick you and your bikes up at the trail head!

Top guest favourite
The exterior of a ranch-style home features covered porches with wooden railings, surrounded by lush greenery and landscaped flower beds. A gravel path leads to the front door, while a metal roof complements the rustic charm of the residence.
Home in Mount Olive
4.92 out of 5 average rating, 25 reviews

Shelby Creek

Take a short gravel drive and be transported to real country living. Our guests say it is peaceful and quiet, hidden away from the hustle of life. The home is a retreat for travelers, spacious for work crews, a weekend getaway, or a family vacation. Three bedrooms +2 full baths, sleeps 8 comfortably, with an open kitchen/dining/living room concept. Minutes away from the highly traveled Hwy 49, the home is conveniently located between Jackson, Hattiesburg, and Laurel.

Top guest favourite
Tiny home in Collins
5 out of 5 average rating, 19 reviews

Cozy Cottage!

This tranquil rustic destination spans six acres and includes a play area for young children, a pavilion, and an outdoor fire pit. Conveniently located just 0.5 miles from Grand Paradise Water Park and the veterans memorial home, and five miles from the Okatoma River, this charming cottage offers a warm space for families to gather and create lasting memories. Also, a lot of great restaurants nearby to satisfy your hunger within 0.5 miles.

Top guest favourite
The front porch of a charming house features a roof overhead with decorative plants hanging from the beams. Several potted plants accent the porch steps, and a set of simple chairs is positioned for relaxation. A path made of stone leads to the entrance.
Home in Jayess
4.85 out of 5 average rating, 184 reviews

Quite Country Style Stay W/ WiFi

It’s an old house out in the country with lots of character & very cozy!! Not A HOTEL SUITE!! If your looking for piece & quiet, its there..:) I also have things on hand there if you need something.. extra sheets, bathroom things, kitchen condiments and seasoning.. I also have an extra full size air mattress & por-ta-crib Everything has WiFi , no cable just TVs and DVD players .. There’s 3 smart tvs 1 regular tv. They all have Roku ..

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, 145 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.

Popular amenities for Prentiss holiday rentals