Holiday rentals in Tupelo

4.82 out of 5 average rating, 188 reviews

Fenced back yard + no extra fees

Our home boasts Mid-Century style & a very large fenced in back yard in the heart of Tupelo! Keep it simple at this peaceful & centrally-located home. Everything you need to see or place to be is within 5 miles of this unique property. No fees! (excludes Airbnb fees as we aren’t in control of those) Bedroom 1- King Bedroom 2- King 1 full bath 1 half bath Large kitchen, large bedrooms, living room (queen sofa bed + very comfy air mattress if needed!) & dining room Pets allowed w/ doggy door

4.91 out of 5 average rating, 116 reviews

Cottage in Tupelo

Historic Mill Cottage-In the Heart of Downtown

Located in the heart of Mill Village! This 2 bedroom/2bath cottage has nice time period updates while maintaining its charm and appeal. The exterior boasts a relaxing front porch and entertaining wrap around side deck. This house also has a relaxing private patio. The detached carport is tucked away to the side rear of the house. The warm character of this cottage is sure to charm. Tupelo's infamous train comes through downtown several times day/night. So be aware if you are a light sleeper!

4.96 out of 5 average rating, 283 reviews

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

4.91 out of 5 average rating, 197 reviews

Cottage in Tupelo

Cozy Cottage with Fenced Backyard!

Work remotely or simply relax at this peaceful and centrally-located cottage in one of Tupelo’s most sought after residential areas. Our home is perfect for a morning walk, remote work with high speed internet and located close to everything. We are an 8 minute drive to Elvis’ birthplace and Furniture Market. 5 minute drive to downtown, 45 minutes to Oxford and an hour to Starkville. In the evening, relax under the stars and string lights with dinner and cocktails on our back porch.

4.99 out of 5 average rating, 149 reviews

Cottage in Blue Springs

WindSong NO Cleaning Fees Long Stay 15% & 45% Disc

“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.

Superhost

Cabin in Tupelo

4.84 out of 5 average rating, 103 reviews

The Lakehouse at Colline Rouge (Red Hill)

Lake house Living with this spacious 4 Bedroom 2 Bath Location right on the edge of Tupelo,MS. Enjoy watching Deer and Turkey from the Back porch with Fireplace Both Inside and Out with Beautiful View of the 16 Acre Lake. Roomy Kitchen, Great for Family outings or Couples Gettaway. There are King size beds in 2 Bedrooms and a Queen Sized in the 3rd. In the 4th BR there are 2 Separate Bunks Beds.....(Full on bottom, twin on top with easy access steps, the 2nd bunk has a Full & Twin.

5 out of 5 average rating, 105 reviews

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.

4.9 out of 5 average rating, 617 reviews

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!

4.84 out of 5 average rating, 103 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!

4.97 out of 5 average rating, 314 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.

4.98 out of 5 average rating, 383 reviews

The Tupelo Honey House Historic & Renovated - 2BR

Enjoy a stylish and comfortable experience located in Tupelo, MS. Whether you’re here for work or just for fun, our hope is that you can kick back and relax in this calm space. We are just minutes from I-22, the birthplace of Elvis and downtown Tupelo. There is plenty of parking at the Tupelo Honey House too. We love Tupelo and are happy to answer any questions.

4.99 out of 5 average rating, 480 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.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Tupelo holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Tupelo

Tiny home in Pontotoc County

5 out of 5 average rating, 12 reviews

Cypress - NEW Tiny Cottage @ Moon Lake Farm

JolynnRating, 5 stars2 months ago

We had the best time here . My husband and I wanted a peaceful night away and that’s exactly what we got . Beautiful, quiet place to get away and spend some quality time together .

Superhost

4.86 out of 5 average rating, 51 reviews

Garage Guest Suite

CarolineRating, 5 stars1 week ago

Shane's place is located in a beautiful historic downtown neighborhood, close to anything one chooses to do in Tupelo. Shane was very responsive whenever we had a need or question. The space was private and peaceful. The bed was comfortable and restful. We'll definitely use Shane's place again if ever the need arises. The price beats the local hotels! I recommend it!

4.96 out of 5 average rating, 95 reviews

Cabin in New Houlka

Deer Camp

TonjiaRating, 5 stars3 weeks ago

We always enjoy our stay in the cabin, it’s so peaceful and it’s always clean !!

4.93 out of 5 average rating, 15 reviews

The Blue Moon Airbnb

DianeRating, 5 stars4 days ago

Our Blue Moon stay was exactly what you hope to get from AirBnB…easy access, exceptionally thoughtful and comfortable furnishings, cool atmosphere (and artwork/decor ☺️), generously supplied toiletries/kitchen essentials and a convenient and private location. The home was spotless and gave our group of out-of-town cousins room to enjoy a family wedding. Ashley was a perfect host, going way beyond to find and mail a forgotten item and we appreciate her assistance and helpfulness. Book the house…you won’t be disappointed!

4.84 out of 5 average rating, 51 reviews

King City Suite

AndrewRating, 5 stars1 week ago

Excellent place to stay. A comfortable walk for a reasonably healthy person to downtown, just take Jefferson, not Main. Parking and getting in and out are easy. Coffee shop just a few feet away. House is very nice and functional. Comfortable bed and no signs of dogs from previous stays. Tupelo was lovley and if I go back I would stay here again.

4.99 out of 5 average rating, 69 reviews

New S. Broadway Cottage in Historic Mill Village

LisaRating, 5 stars2 weeks ago

This was our first experience with Air BnB and we were very satisfied! The house was a perfect size for the 5 of us, plus our dog. Very clean and a great quiet location. There is a train that I slept through but it might benefit others to bring a noise machine or earplugs if they are easily awakened. The location was perfect for eating, shopping and getting to our family’s wedding venue. I would definitely recommend this place and Jay made it extremely easy to check in/out and was responsive to messages quickly. Maybe we will see you in the future!

4.98 out of 5 average rating, 64 reviews

Unwind at Swallow Lane

ShakiaRating, 5 stars4 days ago

We enjoyed our stay here for a weekend getaway to visit family. Once I read through the instructions, check in was easy. The home was beautiful and space for us and our dog. The weather wasn’t in our favor so we didn’t get to enjoy the patio area but overall, we enjoyed our time here and will look into coming back in the near future. Anthony was a great host and super responsive!