Holiday rentals in Toccopola

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

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.

Nov Discount Book 2 Get 1 FREE 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.

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.

The Barn- Luxurious & Unique farmstay getaway

GETAWAY, RETREAT, RELAX, ESCAPE-10 easy minutes to the Square & Campus, our 2/2 Barndominium is a rare experience in peaceful setting with a King en suite BR, 2nd Full BR. fully furnished kitchen, coffee/tea bar, a deep, south facing back porch has a fire pit & grill patio for your outdoors hang out. Expansive glass west end wall allows view of meadow & deer. Indoor/outdoor bar & movie/projector facilities in the east end. Staying at The Barn creates magical memories to be treasured.

Bright & Airy - The Oxford Retreat, Walk to Games

Just a short walk to the Ole Miss stadiums, The Oxford Retreat is your perfect home base for both excitement and relaxation! Enjoy two spacious master suites, each with its own private full bathroom, ensuring comfort and privacy for all. Stay connected with high-speed internet, make your favorite meals in the fully equipped kitchen, and unwind on the patio while taking in beautiful courtyard views. This vibrant retreat has everything you need for an unforgettable Oxford experience!

The Cottage in Downtown New Albany, MS

Come and enjoy The Cottage in Downtown New Albany, MS! This newly renovated property boasts detailed interiors and modern luxuries, while still maintaining the cozy comforts of a weekend cottage. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

The Queen on Cleveland

Come and enjoy The Queen on Cleveland in Downtown New Albany, MS! This new AirBNB is a sister property to “The Cottage”. This newly renovated home boasts detailed interiors and modern luxuries. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

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.

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.

The Tupelo Honey House Historic & Renovated - 2BR

Welcome to the Tupelo Honey Hous - stylish, cozy home in Tupelo—just minutes from downtown, I-22, and Elvis Presley’s Birthplace. Plenty of parking and a calm space to relax after exploring! ✨ Thoughtfully decorated with comfort in mind 🛋 Open living area for relaxing or working remotely ❄️ Climate-controlled for year-round comfort

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)