Holiday rentals in Tupelo

4.96 out of 5 average rating, 302 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.

Guest house 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

4.98 out of 5 average rating, 135 reviews

A pathway of stone steps leads from the lush green lawn to the entrance of the rustic carriage house. A wooden swing hangs nearby, providing a place to relax. The exterior features a combination of brick and wood, surrounded by trees.

Cottage in Amory

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).

4.99 out of 5 average rating, 170 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.

4.98 out of 5 average rating, 43 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

Get away from it all ! Our tiny home is a labor of love created by our own hands. It has a rustic interior with tongue and groove ceilings and walls. The bathroom has a clawfoot tub under dimmable lighting for a relaxing soak. Cast your cares away as you walk the grounds of our family farm. A fire ring is available in the pasture a short distance (approx 100 yards) from the tiny home. Enjoy the glow of a fire underneath the stars. All new - tv, mini fridge and microwave.

4.9 out of 5 average rating, 640 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, 118 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!

4.86 out of 5 average rating, 133 reviews

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.

Guest house in Tupelo

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!

4.91 out of 5 average rating, 219 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 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.

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, 365 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.

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, 419 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, 221 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!

4.99 out of 5 average rating, 506 reviews

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.

Guest house in Tupelo

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.

Popular amenities for Tupelo holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Tupelo

4.92 out of 5 average rating, 264 reviews

The exterior of the carriage house apartment is surrounded by manicured greenery and flowering shrubs. A shaded porch supported by wooden beams invites relaxation. A lawn extends in front, complementing the natural landscape of the property.

Flat in New Albany

A Carriage Apartment at Possumhaw

5 out of 5 average rating, 88 reviews

A charming farmhouse exterior features a red metal roof and a welcoming front porch with rocking chairs. Lush greenery surrounds the porch, with colorful plants and flower beds lining the walkway. Two dormer windows add character to the roofline.

Farm stay in Belmont

Farm Stay - Savannah's Sanctuary - Rock Creek Farm

A charming two-story house is highlighted by a metal roof and surrounded by greenery. Sunlight filters through the trees, casting a warm glow on the exterior. A gravel path leads to the entrance, and bushes frame the front yard.

4.83 out of 5 average rating, 12 reviews

Cul-de-sac

A charming white brick exterior presents a renovated home, featuring a sloped roof and decorative gables. Two symmetrical windows frame the entrance, while well-maintained landscaping enhances the inviting facade. The front porch is accentuated by a decorative door with a diamond-shaped window.

4.97 out of 5 average rating, 30 reviews

The Blue Moon Airbnb

Superhost

A rustic cabin with wooden siding features a steeply pitched roof and multiple windows. The front porch is adorned with wooden railings and seating. A stone chimney rises from the right side, framed by neatly landscaped areas, set against a cloudy sky.

Cabin in Fulton

4.82 out of 5 average rating, 33 reviews

Cabins At Midway, Tombigbee

4.94 out of 5 average rating, 313 reviews

A bright living area features a comfortable sofa adorned with decorative pillows beside a coffee table. A dining area with a round table is surrounded by stylish woven chairs. Large windows allow ample natural light, with elegant curtains complementing the space.

Home in New Albany

TallahatchieTownhouse | Downtown ON the Tanglefoot

Home in Mooreville

4.57 out of 5 average rating, 23 reviews

Ole Rustic Cottage

A single-story home with a clearly defined entryway features white brick exterior and a combination of dark shutters and light trim. A well-maintained front yard includes a neatly manicured lawn and a pathway leading to the front door. Ample natural light is present from the clear blue sky.