Holiday houses in Calhoun County

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Top-rated holiday rentals in Calhoun County

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Guest favourite
The bedroom features a spacious bed adorned with a soft gray coverlet and an array of decorative pillows. Light-colored curtains frame a window, allowing natural light to illuminate the room. Two bedside lamps provide additional lighting, and a comfortable bench is positioned at the foot of the bed.
Apartment in Calhoun City
4.93 out of 5 average rating, 177 reviews

Comfortable and stylish one bedroom apartment.

We are excited to host you and a loved one (max. of 2 guests) at our 2nd floor (stairs), 1 bedroom/1 bath short-term rental full of character. In this apartment, you will have exclusive access to a spacious, private bedroom and a large, full bathroom and kitchen. If you're looking for a tastefully decorated space with a modern feel but with the ambiance of something historic, we're the perfect spot. Guests aren’t allowed to host “company”. Only reg. guests Read full listing before booking.

Guest favourite
A living area features a spacious brown sofa adorned with patterned cushions and an ottoman. An air conditioning unit is mounted on the wall. A painting of guitars adds color to the room, while a dining area with wooden chairs is visible through an open doorway.
Home in Calhoun City
4.88 out of 5 average rating, 33 reviews

Sweet T’s Hilltop

Sweet T’s Hilltop is located in a rural setting and is nestled on a hill hidden by trees. You will find peace from the hustle and bustle away from cities and towns. This 3 bedroom/1 bath house is 40 minutes from Mississippi State Campus, 30 minutes to Grenada Lake & 20 minutes from Natchez Trace. There is nearby fishing and hunting for those who live for the outdoors along with walking trails and hiking within a few miles. If you are looking for quiet, cozy getaway you have found your place.

Top Guest favourite
A charming 1950s cottage features a yellow exterior and a welcoming front porch adorned with potted plants. The manicured lawn is spacious, bordered by a variety of greenery, creating a serene outdoor setting. Windows allow natural light to brighten the living spaces.
Home in Pontotoc
5 out of 5 average rating, 48 reviews

Buttercup Cottage LLC

History Heritage, & Hospitality! Located on S. Main St. within walking distance of the Tanglefoot Trail and downtown shopping. The 1950s cottage was renovated and kept the original charm and features an eclectic mix of antiques. Relax in the recliner in front of the big screen tv with streaming services and a strong wi-fi signal or use the work space to catch up on emails. The lot is wooded in the back and across the street, so it is peaceful and safe. Located midway between Tupelo & Oxford.

Top Guest favourite
A spacious green lawn surrounds a wooden cabin, featuring a covered porch with wooden steps. Potted plants hang from the beams, while trees provide a natural backdrop, enhancing the sense of privacy and tranquility.
Cabin in Bruce
5 out of 5 average rating, 19 reviews

Hidden private cabin on lake!

Forget your worries in this spacious and serene space. Located just 30 minutes from the college town of Oxford!! Easy access to the city but nestled in the woods for full complete privacy. Big enough to comfortably fit multiple families. Located on over 80 acres with a private lake, fishing dock and all the privacy you want. Equipped with Wi-Fi! Huge open kitchen plan with large customer made dining table table to seat 12! Outdoor dining and grilling area as well as relaxing sitting areas.

Guest favourite
The exterior of a rustic cabin is visible, featuring a screened porch and wooden siding with a metal roof. An American flag hangs from the porch, while fall leaves blanket the green yard, accentuated by a small flower arrangement near the entrance.
Cabin in Coffeeville
4.91 out of 5 average rating, 77 reviews

Fox Hunting, Crappie Fishing Getaway Grenada Lake

My place is close to Grenada Lake Reservoir with great Crappie, Bass and Catfish fishing, Fox Hunters' Kennels and other hunting areas. You’ll love my place because of the outdoor space, Amish built 2016 cabin with loft and screened porch, large back deck. Covered shed for grilling and fish cooking or just relaxing. Located on an Oak trees shady lot good for couples, solo adventurers, families (with kids), hunters and fishermen. Bike, ATV, UTV, horse trails at Choctaw Trails, 5 miles away.

Top Guest favourite
A comfortable leather sofa adorned with decorative throw pillows is positioned near a wooden coffee table. A small mirror reflects warm light from two lamps, while a vase of fresh flowers adds a touch of nature. A compact desk is visible in the background.
Cottage in Blue Springs
4.99 out of 5 average rating, 170 reviews

September-No Cleaning Fees For 2+ nights WS

“Windsong” Spacious studio cottage. Everyone raves... "It feels like home." "It's so cozy." "I could live here." Keurig with K cups ready to enjoy. Lg oversized queen bed is just as comfy as it looks. FiberOptic internet with 43" smart TV with Roku Channel movies and live tv—a firepit for your enjoyment while surrounded by beautiful towering trees and a view of the lake. Roll away twin bed if requested… must request upon booking. 2 Cottages available...great for 2 families get away.

Top Guest favourite
A charming chapel stands surrounded by lush greenery, featuring a prominent steeple and white exterior. Colorful flowers are planted in the garden alongside a white picket fence, creating a serene and inviting atmosphere under a sky dotted with clouds.
Guesthouse in Pontotoc
5 out of 5 average rating, 27 reviews

The Eclectic Chapel of North MS

We have had guests asking if the chapel will be decorated for Christmas. ABSOLUTELY and if you want a few days in December to get in the mood and feel the spirit, what better than the splendor of staying in a chapel. BOOK EARLY! The chapel was formerly a wedding chapel, located in Pontotoc, MS and nestled between Tupelo (Elvis Birthplace) and Oxford (Ole Miss or The University of MS). We are 10 minutes to the Natchez Trace Parkway. If you golf we are 5 minutes from the golf course.

Top Guest favourite
A cozy bedroom features a four-poster bed with a white comforter and decorative pillows. Natural light enters through a nearby window adorned with light curtains. A mirrored accent and bedside lamps contribute to the inviting ambiance, while a stylish cowhide rug adds warmth to the wooden floor.
Farm stay in Oxford
4.99 out of 5 average rating, 421 reviews

The Cottage, 2BR Farm Stay by Velvet Ditch Villas

Escape to The Cottage, a charming farmhouse getaway just 8 miles from Oxford. Set on 4 peaceful acres, this cozy retreat blends vintage and shabby chic décor for a warm, inviting vibe. Start your day with fresh eggs, meet our friendly farm animals, and enjoy evenings by the fire pit under stunning starry skies. Perfect for a romantic escape or quiet retreat, The Cottage offers countryside serenity with easy access to Oxford’s dining, shopping, and entertainment. Book your stay today!!!

Guest favourite
A spacious dining area features a round table surrounded by wooden chairs, complemented by a decorative area rug. Large windows invite natural light and provide views of the outdoors, while a chandelier hangs gracefully overhead, enhancing the room's charming design.
Barn in Oxford
4.97 out of 5 average rating, 120 reviews

The Barn- Luxurious & Unique farmstay getaway

RETREAT, RELAX, ESCAPE-10 easy minutes to the Square, our 2/2 Barndominium is a rare experience in peaceful setting. It has a K en suite BR. 2nd bedroom is a Full. There's a fully furnished kitchen, coffee/tea bar, a deep, south facing back porch with fire pit & grill for your outdoors hang out. We have an outdoor saloon bar & movie/projector facilities in the open end of the barn. Everything you could wish for is provided. Staying at The Barn is a unique experience to be treasured

Top Guest favourite
The historic house is depicted in soft evening light, showcasing an inviting front porch with a swing and decorative columns. Lush greenery and well-maintained flower beds frame the front yard, while the surrounding neighborhood is visible in the background.
Home in Water Valley
4.99 out of 5 average rating, 102 reviews

The Cedars 1863 Guesthouse

My place is close to Downtown, walking distance to the shops, banks, coffeehouses and restaurants. You’ll love my place because it was built in 1863. Whether you are relaxing on the front porch swing, eating a snack on the veranda or maybe just meditating on the back porch, my place offers a quiet place to unwind. My place is good for couples, solo adventurers, and business travelers.

Top Guest favourite
A charming wooden cabin is surrounded by tall trees, featuring a welcoming porch with a seating area. Greenery adorns the entrance, while a small path leads to the cabin's front. The natural setting promotes a tranquil and peaceful atmosphere.
Cabin in Eupora
4.97 out of 5 average rating, 29 reviews

Crystal Creek Cabin

Cozy Cabin Retreat in a Peaceful Setting – Perfect for Two Escape to this charming one-bedroom cabin, nestled in a serene and peaceful environment, perfect for a couple’s getaway or a solo retreat. Whether you're seeking a tranquil space to relax or a comfortable base to explore the surrounding area, this cozy cabin has everything you need for a restful stay.

Top Guest favourite
A cozy sleeping area features a queen bed with white linens and decorative pillows. Colorful artwork adorns the walls, while a dark patterned area rug covers the floor. A plush chaise lounge provides additional seating, complemented by two bedside lamps for soft lighting.
Farm stay in Oxford
4.98 out of 5 average rating, 406 reviews

Art Gallery Apartment

This basement apartment is below Oxford Treehouse Gallery in beautiful Lafayette County. It is nestled in the trees down a private drive only 6.5 miles from the Oxford Square. It has a private entrance with an outside covered seating area and access to the screened porch off the gallery.

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