Holiday rentals in Pontotoc County

Cypress - NEW Tiny Cottage @ Moon Lake Farm

Custom tiny cottage tucked in the woods beside the lake on Moon Lake Farm. This special cottage was made just for your family outing, romantic getaway, or bachelorette party. Enjoy the hot tub, paddle and fish the lake, walk the pasture, or just soak in the nature. Conveniently located one mile outside of Tupelo. -Hot tub -Firepit -Full kitchen -Washer dryer -Sleeps 6 to 8 -Nature trails -Lake: fish, swim, paddle boat -Enjoy the animals: mini donkeys, chickens, horses -Farm fresh eggs

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.

The Eclectic Chapel of North MS

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). Pontotoc is home the Bodock Festival, its on the Blues Trail, The center of The Rails to Trails Bike Trail and many antique stores. Located 8 miles from Toyota in Blue Springs, MS. We are 8 minutes from The Cherry Creek Orchard and 10 minutes to the Natchez Trace Parkway. If you golf we are 5 minutes from the golf course.

Highland House

Experience Southern charm and modern comfort at Highland House. Located just 32 miles from Ole Miss, 23 miles from Elvis Presley's birthplace, and a stone's throw from the Tanglefoot Trail, this stylish property offers the perfect blend of convenience and relaxation. Whether you're here for a weekend retreat or an extended vacation, Highland House is your home away from home in the heart of the south. Create unforgettable memories and experience the charm of Pontotoc.

Nanny’s Place

Relax with the whole family in our peaceful, modern home located just 20 miles from Oxford and Ole Miss, 24 miles from Tupelo Airport, and 15 miles from New Albany. Built only 4 years ago, the home is clean, bright, and comfortable, perfect for families, couples, or small groups looking for a quiet getaway near Oxford. You’ll enjoy a cozy living area, a fully equipped kitchen, and comfortable bedrooms. Need more space? We provide twin air mattresses for extra guests.

Southern Charm Home

Relax with the whole family at this peaceful quiet home. Enjoy the countryside of town while also having access to the city. This home is in the heart of downtown Pontotoc. In walking distance of the Tanglefoot trail, 35 min from Oxford MS home to Ole Miss, and 25 min from Tupelo, MS the birthplace of Elvis Presley. Whether you are here for work or just to unwind, this beautiful, updated home is the perfect place to stay.

The Parsonage

Make yourself at home at the former McGregor Chapel Parsonage - just 20 miles from Oxford and Tupelo. Or stay local and explore Pontotoc’s bustling Amish community. Ride or hike your way on the Tanglefoot Trail - Mississippi’s longest rail-to-trail conversion from New Albany to Houston! The Parsonage is located close enough to Highway 6 to be convenient, but tucked away for a peaceful retreat.

Cul-de-sac

NOW ACCOMMODATING 4 GUESTS!! Forget your worries in this spacious and serene space. Get away from the city and enjoy a beautiful sky full of stars with the sound of nature. Or simply spend time with your family indoors. • 5 minutes from Natchez Trace Pkwy • Center of Tupelo and Pontotoc • 40-50 minutes from Oxford/Ole Miss University

Thaxton Meadows

Bring the whole family to this great place with plenty of space to spread out. The house is 4225 square feet heated/cooled set on 7 acres 20 minutes to Ole Miss and all the amenities of Oxford. 15 minutes to New Albany or Pontotoc and 40 minutes to Tupelo. Seasonal pool is open June 1st-August 31. (Garage access is NOT included)