Holiday houses in Monticello

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Top-rated holiday rentals in Monticello

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

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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, 87 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
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, 143 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
A log cabin is set amid open grassland, surrounded by trees. The structure features a light-colored roof and a porch area, with an American flag gently waving. The expansive grounds provide a sense of tranquility and space, showcasing the natural surroundings.
Cabin in Sontag
4.97 out of 5 average rating, 64 reviews

The Bird Nest

Take it easy at this unique and tranquil log cabin hand built by my grandfather and father from cypress trees pulled straight out of the Louisiana swamps. Escape the city & enjoy the serenity of the country life. Located 15 minutes from Monticello and 25 minutes from Brookhaven. Dollar General located 3 miles away & a country store with fuel 1.5 miles away. This fully furnished 2/1 currently has 1 full size & 1 queen size bed and 5’ shower(not a full tub). Smoking is allowed OUTSIDE ONLY!

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, 104 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
Farm stay in Summit
4.93 out of 5 average rating, 261 reviews

First Fruits Farm

Peaceful Tiny House on 80 acres, including 16 acres of blueberries and blackberries (seasonal)Get away to enjoy beautiful sunrises and sunsets on the screen porch Full kitchen. One bedroom (full size). Loveseat. Shower only.. coffee provided. BREAKFAST i UPON REQUEST. 10 minutes from Interstate 55, between Jackson, Ms and New Orleans. REGISTERED GUESTS only PLEASE INCLUDE the names and ages NO SMOKING; NO PETS. **Will possibly accept reservations less than 24 hrs. Please send inquiry

Top Guest favourite
A cozy loft space features an extensive bookshelf filled with various books. A vintage-style couch is positioned in front, adorned with decorative cushions. A rustic coffee table made from reclaimed wood adds a charming touch to the room, complemented by natural light from the surrounding area.
Apartment in Brookhaven
4.99 out of 5 average rating, 163 reviews

Apartment with Loft

We absolutely love hosting!This space is an apartment built in part of a shop metal building. This was designed by and for our daughter who has since moved and so now using for Airbnb. one queen bed in the loft, one twin XL bed in downstairs bedroom. couch lets out to twin bed but I would only recommend for children….as it is small. To be comfortable, you may want to ask options for more than 3 . Bathroom opens to bedroom. Please note: Shower is small. There is no TV, but great WiFi.

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, 104 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
4.94 out of 5 average rating, 50 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 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, 182 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, 141 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
A bright kitchen features white cabinetry and stainless steel appliances, including a double oven and refrigerator. A large wooden island with a gas cooktop serves as a central workspace, complemented by light wood flooring. Natural light floods in through windows, creating an inviting cooking area.
Home in Columbia
4.98 out of 5 average rating, 148 reviews

Classy in the Country -3 BR House

Unwind in style at our elegant 3-bedroom, 2-bath countryside retreat, just 2 miles from town. Whether you’re visiting for business or a well-deserved getaway, our beautifully designed home offers the perfect blend of comfort and class. Come solo, with a partner, or bring the whole family—there’s plenty of space for everyone to relax, recharge, and feel right at home.

Guest favourite
A cozy porch area features a hanging chair with plush cushions, paired with a sofa adorned with orange accents. A patterned rug adds texture, and a lush hanging plant is suspended above, providing a touch of nature against the backdrop of greenery.
Treehouse in Pike County
4.91 out of 5 average rating, 298 reviews

Riverfront Cabin w/ Firepit, Outdoor Tub, Kayaks!

Enjoy the tranquility of the Bogue Chitto river in the freshly renovated Blue Heron Cabin. This modern waterfront cabin sits on 3 acres and offers beautiful views of the river and nature. The cabin is bright and cozy and provides many outdoor spaces, including a screened in porch, an outdoor shower, outdoor tub, and kayaks available for your use!

Popular amenities for Monticello holiday rentals