Vacation rentals in Pontotoc County

4.96 out of 5 average rating, 293 reviews

A cozy outdoor area features a circular stone fire pit surrounded by four comfortable chairs. A small sign indicating parking is visible in the foreground, with a quaint cottage set among lush greenery in the background.

Guesthouse in Ecru

The Doughboys Cottage

Private full bath Queen Bed Cottage near Natchez Trace Park & Mississippi's premier biking destination, Tanglefoot Trail. Perfect for single or double occupancy. 25 miles from Elvis Presley Birthplace 35 miles from The University of Mississippi and Rowan Oak, the home of William Faulkner. Enjoy a fresh pan of The Doughboys Fresh Baked Cinnamon Sticky Buns $13.00. Delivered to your door in a.m. Local venues: Great Mexican Restaurant 2 miles Walmart 3 Miles Convenient Store 1/4 mile

Tiny home in Pontotoc County

The cottage is shown illuminated at night, surrounded by tall, bare trees. The structure features a front porch with a light fixture, highlighting the inviting entrance. A gravel path leads to the cottage, with gentle shadows cast by the moonlight.

5 out of 5 average rating, 16 reviews

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

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.

5 out of 5 average rating, 45 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.

5 out of 5 average rating, 16 reviews

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

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.

An outdoor area features a spacious pool surrounded by a textured pavement, flanked by a grassy lawn. A covered porch is visible to the left, with a distant view of a dual-gabled structure. Lush green trees provide shade in the background.

4.82 out of 5 average rating, 11 reviews

An outdoor paradise

Just a short drive to the Grove or Vaught Hemingway stadium! Enjoy the outdoor amenities of a covered back porch with TV’s and a bar. Cool off in the pool or throw burgers on the grill. Spacious living room and kitchen with plenty of room for the weekend. Master bedroom with king size bed that has a shower with four shower heads. Bedroom #2 has a queen size bed with tv and spacious bathroom to get ready for the game. Bedroom #3 a kids full size bed complete with toys for the little ones

A spacious living room showcases comfortable seating arrangements, including a gray sectional sofa and a recliner. A coffee table is centered on a soft area rug, with decorative accents like a globe and framed artwork. Natural light filters through several window treatments.

4.98 out of 5 average rating, 44 reviews

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.

A welcoming single-story house is situated under a clear blue sky. A covered porch features seating, surrounded by green grass and landscaping. A gravel pathway leads up to the entrance, enhancing the home's accessibility and charm.

Home in Thaxton

5 out of 5 average rating, 4 reviews

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.

The exterior of a charming house is depicted under a clear blue sky. Lush greenery surrounds the home, with a well-maintained lawn and various plants near the entrance. A welcoming front porch features wooden rails, and the house combines light and dark siding elements.

4.64 out of 5 average rating, 14 reviews

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 exterior of a spacious manufactured home is shown, featuring a metal roof and large windows with red shutters. Green grass surrounds the home, while tall trees provide natural shade. A front porch stairs leads to the entrance, enhancing accessibility.

4.98 out of 5 average rating, 47 reviews

South Centerpoint

Whether you're visiting family and friends or staying close to Ole Miss, you and your family will have everything you need here for a few nights away from home. This comfortbale and spacious manufactured home was built in 2002. While here, enjoy our many local restaurants, visit Ole Miss, or enjoy Pontotoc's farmers market. We're also 10 miles from the Amish community and 20 miles from Elvis Presley's birth place.

A spacious bed is centered in the room, dressed in white linens with teal accent pillows. Flanking the bed are two white nightstands. A potted plant adds greenery to the corner, while a soft area rug with a geometric pattern complements the hardwood floor.

4.86 out of 5 average rating, 22 reviews

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.

4.82 out of 5 average rating, 11 reviews

A charming two-story house is highlighted by a metal roof and surrounded by greenery. Sunlight filters through the trees, casting a warm glow on the exterior. A gravel path leads to the entrance, and bushes frame the front yard.

Home in Tupelo

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