Holiday rentals in Tupelo

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

September-No Cleaning Fees For 2+ nights 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 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!

Beach house

Adorable tiny home behind the main house in the backyard; quiet neighborhood in the heart of Tupelo. One bedroom/loft, full bathroom with small kitchen. A Living room with tv. Sip coffee on the porch with breakfast table. Enjoy your evening by the fire pit or on the deck. Many dining and shopping options nearby or take a stroll downtown just 5 minutes away. See Elvis’ birthplace and museum 10 minutes away or enjoy a walk at the park! All within a 10 mile radius!

Central Tupelo Guesthouse with Pool

Centrally located in one of Tupelo’s historic neighborhoods, just minutes away from local eateries, parks, shops, Cadence Bank Arena, Tupelo Regional Airport, as well as the birthplace of Elvis Presley. Our space is recently 100% renovated and ready for your peaceful stay, complete with a large kitchen area, queen size bed, a spacious walk-in shower, as well as access to the pool. This stay was originally known as Duckingham Palace.

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.

Historic Charm Near Downtown Tupelo

Newly remodeled historic home less than a mile from Downtown Tupelo where you can enjoy shopping and plenty of tasty restaurants. The house has been thoughtfully furnished in a fun, midcentury modern style. The beds are very comfortable and the master bathroom has a giant shower and separate soaking tub to enjoy after a long day. Please note the house is close to the famous downtown train so you may hear the engine horn at night.

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

Honey Pot

I think you will enjoy staying at our beautiful guest home addition on Riverbirch golf course. You can walk or run in our safe neighborhood or bring your clubs for an evening of golf. Pets may be allowed for a small additional fee - Please discuss with me prior to your booking. I enjoy social media and provide high speed internet

The Apiary

Our private homestead is the perfect setting for your getaway. You’ll have the best of both worlds—with 20 acres of privacy with all the excitement of Tupelo just miles away. While here, you can relax in the serene outdoors while watching our farm animals graze. You can also gather eggs and enjoy them for breakfast!

Cozy Guest House in Downtown Tupelo

Private cozy one bedroom with a bathroom guesthouse available. It is conveniently located in downtown Tupelo. Private entrance and includes wifi, roku tv, microwave, mini fridge, and Keurig coffee maker. Within walking distance to downtown Tupelo with great Restaurants.