Vacation rentals in Tupelo

4.96 out of 5 average rating, 301 reviews

A cozy outdoor area features a circular stone fire pit surrounded by four comfortable chairs. A small sign indicating parking is visible in the foreground, with a quaint cottage set among lush greenery in the background.

Guesthouse in Ecru

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

4.99 out of 5 average rating, 169 reviews

A comfortable leather sofa adorned with decorative throw pillows is positioned near a wooden coffee table. A small mirror reflects warm light from two lamps, while a vase of fresh flowers adds a touch of nature. A compact desk is visible in the background.

Cottage in Blue Springs

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.

4.9 out of 5 average rating, 638 reviews

A living room features a dark blue couch adorned with decorative pillows, positioned near large windows dressed with light curtains. A coffee table sits centrally, displaying a stack of books and small plants. Wall sconces and a mirror add to the room's inviting ambiance.

Cottage in New Albany

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!

4.98 out of 5 average rating, 117 reviews

The exterior of a newly renovated home features a charming front porch supported by decorative columns. Large windows allow natural light to illuminate the space, while a well-maintained lawn and neatly arranged shrubs enhance the welcoming entryway.

Home in New Albany

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!

The entryway features a door marked 'Beach House,' leading to a living area with a soft gray couch. A flat-screen TV is mounted on the wall, while natural light enters through a nearby window. Wood paneling adds warmth to the space.

4.86 out of 5 average rating, 129 reviews

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!

The exterior of a historic home features a covered porch with American flag accents. Potted ferns hang from the ceiling, flanking two chairs and a small table. A stone walkway leads to the entrance, surrounded by landscaped greenery and blooming flowers.

4.98 out of 5 average rating, 362 reviews

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.

4.91 out of 5 average rating, 217 reviews

A cottage with dark blue siding is framed by neatly trimmed bushes and green grass. A covered porch features a bench alongside the main entrance, while tall trees provide shade in the background. A gravel driveway leads up to the home, adding to its inviting curb appeal.

Cottage in Tupelo

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 exterior of a renovated house is displayed, featuring a welcoming front porch with wooden steps. Lush trees surround the property, enhancing the tranquil setting. A gravel pathway leads from the porch to the yard, where a patch of grass complements the natural surroundings.

4.98 out of 5 average rating, 415 reviews

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

4.95 out of 5 average rating, 220 reviews

An open-concept living and dining area is showcased, featuring a spacious seating area with a light-colored couch. A dining table with seating for multiple guests is positioned near the kitchen, which includes modern appliances. A flat-screen TV is mounted on the wall, complemented by warm lighting.

Farm stay in Tupelo

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!

A fenced entrance is framed by brick pillars and a wrought iron gate. Beyond the gate, a gravel pathway leads to a private outdoor area with seating, flowering plants, and a small fountain. Lush greenery surrounds the space, providing a sense of privacy.

4.99 out of 5 average rating, 504 reviews

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.

4.95 out of 5 average rating, 109 reviews

A living area features two comfortable sofas surrounding a wooden coffee table. A vintage-style cabinet is set against the wall, and a television is mounted above it. Deer mounts add a rustic touch to the wood-paneled walls, enhancing the cabin's character.

Cabin in New Houlka

Deer Camp

This cabin is located 1/4 mile from the Tanglefoot Trail. There are two grills at the cabin. A fishing pond is located behind the cabin. Air mattresses are in the laundry room for additional guests. Feel free to use condiments or anything else in the refrigerator.

The exterior of a spacious brick home is displayed, featuring a welcoming front porch and well-maintained landscaping. A manicured lawn with colorful shrubs complements the structure. The driveway provides access to parking in front of the home under a clear blue sky.

4.89 out of 5 average rating, 171 reviews

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!

Popular amenities for Tupelo places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Tupelo

4.95 out of 5 average rating, 20 reviews

A rustic wooden cabin is nestled among tall trees, with a porch supported by beams. Chairs are arranged on the porch, and large windows allow natural light to enter. The surrounding grassy area is dotted with pine needles, enhancing the cabin's secluded feel.

Tiny home in Shannon

Pontocola Pines Off Natchez Trace. Pontocola Rd.

Tiny home in Pontotoc County

The cottage is shown illuminated at night, surrounded by tall, bare trees. The structure features a front porch with a light fixture, highlighting the inviting entrance. A gravel path leads to the cottage, with gentle shadows cast by the moonlight.

5 out of 5 average rating, 19 reviews

Cypress - NEW Tiny Cottage @ Moon Lake Farm

A single-story guest house is shown, featuring a well-maintained exterior with a gray facade. Green trees surround the property, and colorful azalea bushes add a pop of color to the landscaping. A clear blue sky can be seen above, enhancing the welcoming ambiance.

5 out of 5 average rating, 18 reviews

The Sugar Magnolia *no cleaning fee

Superhost

A guest room features a queen size bed with a light gray and beige coverlet, complemented by two armchairs and a round pouf. A coffee station with a Keurig machine is present on a side table. Soft lighting from lamps enhances the room's calm atmosphere.

4.86 out of 5 average rating, 57 reviews

Garage Guest Suite

Superhost

A rustic cabin is situated among lush greenery, featuring a wooden exterior with green trim. A porch wrapped in railings offers access to a large door, enhancing the inviting entrance. The roof is sloped, and the natural surroundings provide a peaceful backdrop.

Cabin in Nettleton

5 out of 5 average rating, 3 reviews

King Kahuna Fishing Cabin

4.98 out of 5 average rating, 41 reviews

A cozy sleeping area is presented, featuring a spacious bed with layered blankets and decorative pillows. A wooden barn door leads to a bathroom tucked behind the main space. The walls showcase natural wood paneling, complementing the rustic aesthetic.

Tiny home in Guntown

Quaint Guest Suite in country - outside of Tupelo

4.95 out of 5 average rating, 38 reviews

A spacious living area presents a contemporary design with exposed wooden beams and stylish lighting fixtures. A comfortable sofa is positioned across from a wall-mounted smart TV. A dining table with elegant chairs is visible in the distance, leading to a balcony door that opens to outdoor views.

Apartment in Tupelo

Luxury Downtown Loft & Balcony

A living area features a dark sectional couch adorned with colorful patterned cushions. A round table made of wood sits in front, accompanied by a decorative stool. Bright artwork is displayed on the orange wall, and a tall, multicolored light adds a modern touch near the window.