Vacation rentals 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

Value · Family · Checkout

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.

Value · Family · Layout

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.

Value · Family · Long stay

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!

Value · Location · TV

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!

Location · Family · Bathroom

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.

Location · Family · Backyard

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.

Location · Family · Kitchen

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.

Location · Value · Check-in

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.

Family · Value · Cleanliness

Unwind at Swallow Lane

Unwind and enjoy easy access to everything from this centrally located home, here in Tupelo, Ms. It’s super spacious and chic, whether you’re cooking in the kitchen, relaxing in the living room, or enjoying the closed-in patio. It has a outdoor bar area, as well as a fenced in yard. We have card/ board games, cornhole boards, and a fools ball table. There's enough fun for the adults and the kids.

Location · Family · Pets

The Convenient

Keep it simple at this peaceful and centrally-located place. This studio apartment is conveniently located just off the town Square in Pontotoc. Only steps away from banks, boutiques, restaurants and fitness centers. Approximately 35 minutes to Oxford and 25 minutes to Tupelo. Self check in and on site parking.

Location · Getting around · Comfort

A Carriage Apartment at Possumhaw

This carriage house apartment is located in the beautiful small town of New Albany. The carriage house is part of a 25 acre estate we call Possumhaw, located just off of I22. The property is convenient to historic downtown (2 miles) and the Tanglefoot Trail (1.5 miles).

Family · Value · Air conditioning