Holiday houses in Pontotoc

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

The Eclectic Chapel •in the center of North MS

The chapel was formerly a wedding chapel, in Pontotoc,MS and located between Tupelo (Elvis birthplace) and Oxford (home of Ole Miss). Pontotoc is home of the Bodock festival, it’s on the Blues Trail, and is the center of the Rails to Trails Bike Trail and antique stores. We are 8 miles from the Toyota manufacturing facility in Blue Springs. We are 8 miles to Cherry Creek Orchard and 10 minutes to the Natchez Trace Parkway. And if you golf, we are 5 minutes from Pontotoc Country Club.

Unique Barndominium Private Retreat Experience

*Converted barn, incredible accommodations, more than just another place to stay. *10 minutes to Square & Campus *KING en suite *2nd FULL BR *Wi-Fi *Parking *Furnished kitchen w/ice machine *Coffee/tea bar *Movie theater w/projector & screen (seasonal use) *POOL-across the driveway *Lg back porch with picnic table *Patio with fire pit & grill *Indoor/outdoor Bar *Peaceful view of meadow, mixed woods forest *Gazebo *Unique experience *Dogwash station BOOK your getaway now or WISHLIST us.

Large Studio Cottage/Quiet & Peaceful 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 Lakehouse at Colline Rouge (Red Hill)

Lake house Living with this spacious 4 Bedroom 2 Bath Location right on the edge of Tupelo,MS. Enjoy watching Deer and Turkey from the Back porch with Fireplace Both Inside and Out with Beautiful View of the 16 Acre Lake. Roomy Kitchen, Great for Family outings or Couples Gettaway. There are King size beds in 2 Bedrooms and a Queen Sized in the 3rd. In the 4th BR there are 2 Separate Bunks Beds.....(Full on bottom, twin on top with easy access steps, the 2nd bunk has a Full & Twin.

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!

Amish Home on an Alpaca Farm

Nestled between Oxford, MS and Tupelo, MS, this former Amish Farmstore has been renovated to include electricity and modern plumbing while maintaining its simple Amish charm. Enjoy views of the rolling hills and resident alpacas while sipping coffee on the back porch. Shop for unique gift items in the farm store on site & visit the active Amish community located just a few blocks away. The tanglefoot trail runs through town. Trail Transportation available Fri/Sat (small fee)

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!

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.

Back in Time (Oxford Overflow)

Located central to Oxford (30 minutes away), Tupelo (25 minutes) and New Albany (20 minutes). This new apartment is furnished in vintage rock and 70's pieces with a cozy at-home feel. It's in a very quiet area set off a dirt road, surrounded by rolling hills. A quaint coffee/wine bar will make you feel welcomed upon arrival and refreshed before you leave. One small (40 lbs or less) well-behaved fur baby is welcome, keep your fur baby leashed and tidy up after them.

Cozy Dog-Friendly Cottage Near Downtown Tupelo

Settle into comfort at this cozy, dog-friendly cottage near Downtown Tupelo and Elvis’ Birthplace. With fast WiFi, same-day check-in, and a peaceful neighborhood, it’s ideal for remote workers, family visits, and travelers headed to the coast. Enjoy reliable Superhost care, safe parking, and home-style amenities close to restaurants, shops, and Tupelo’s top attractions—a welcoming space designed for easy living and stress-free stays.

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.