Holiday rentals with outdoor seating 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

The Nook (on the Tenn-Tom)

Located on the Tenn-Tom River just 1 mile from DownTown, this 500 sq ft upstairs carriage house will relax you with its waterfront view. The exterior is rustic continuing with cottage charm inside. You can relax on the sofa in the comfort of the living room, take a quiet nap in the bedroom or enjoy a game of PacMan. Try grilling with a great water view on the porch or swing. For a change of pace, 2 kayaks & a canoe are for your enjoyment! 🛶 (Twin bed w/trundle downstairs for another guest).

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 Heights - Town & Country Living

Welcome to The Heights! For Starters, you will be greeted with a fresh pan of Talbot Cinnamon Rolls.* For stays three nights and longer, you will also find a cheese, meat, cracker platter in the fridge. The kitchen is equipped with a Keurig coffee maker(drip and K-Cup) with coffee! The fridge is stocked with water, juice and sparkling water. This 70's era home has been immaculately cared for and has the comfort of 3 Bedrooms, two bathrooms, Living Room, and a complete kitchen.

The Barn- Luxurious & Unique farmstay getaway

RETREAT, RELAX, ESCAPE-10 easy minutes to the Square, our 2/2 Barndominium is a rare experience in peaceful setting. It has a K en suite BR. 2nd bedroom is a Full. There's a fully furnished kitchen, coffee/tea bar, a deep, south facing back porch with fire pit & grill for your outdoors hang out. We have an outdoor saloon bar & movie/projector facilities in the open end of the barn. Everything you could wish for is provided. Staying at The Barn is a unique experience to be treasured

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!

Cozy Tupelo Getaway | Dog Friendly | Near Downtown

Relax in this cozy, dog-friendly retreat near Elvis’ Birthplace and downtown Tupelo. Perfect for road trips, remote work, or extended stays with fast WiFi, comfy beds, and a quiet neighborhood. Enjoy peaceful mornings, evening cocktails under string lights, and easy access to I-22, Oxford, and Starkville. Superhost care, self check-in, and all the comforts of home await you and your pup.

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!

The Bristow Bungalow - Great Location & Backyard

FRESH, CLEAN, & MODERN AIRBNB! This space has everything you need: Gorgeous kitchen, hardwood floors, amazing deck w/ large backyard, and beautifully designed bedrooms. Down the street from a cute park & minutes away from downtown, restaurants, & stores!