Holiday rentals in Cleveland

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Top-rated holiday rentals in Cleveland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior showcases a single-story house with a brick facade and a blue metal roof. Lush greenery and flowering plants are arranged along the front, complementing the palm tree near the entrance. A driveway leads up to an overhang and parked vehicle, with a lawn stretching across the front.
Home in Leland
4.98 out of 5 average rating, 131 reviews

“Pink on the Creek”Guest House

Longer stay discounts . No cleaning fee! VERY SAFE AREA IN THE HEART OF THE MISSISSIPPI DELTA WHERE THE BLUES WAS BORN! Extra charge per person per night after 4. Max is 6. Better than just a motel room. A bit of antique & modern, though greatly cared for, shows age in some places, loving wear, quaint aging & charming patina both inside and outside, is super clean/sanitized. You will love it. Very Affordable for a whole house in this area. A selection of pillows. Your comfort is our priority.

Guest favourite
A cozy bedroom features a spacious bed dressed in light pink linens. Two windows allow natural light, complemented by decorative wall art. A comfortable gray armchair and side table are positioned nearby, while warm lighting fixtures create a gentle ambiance in the room.
Guest house in Cleveland
4.92 out of 5 average rating, 64 reviews

Renovated Luxury Guest Suite

Kick back and relax in this calm, stylish space! Perfect for a couples getaway, family visits, or a weekend of activities. This newly renovated 1BR/1 Bath separated guest suite is in the heart of the delta. Attached to a outdoor seating space/hangout with its own keyless entry separate from the home. We are located in a safe neighborhood with access to the country club and golf course. With a 2 min drive to down town and Delta State University we are perfect located in the center of the city!

Superhost
A single-story home presents a classic brick façade with a prominent garage. The well-kept yard features neatly trimmed shrubs and lush greenery. The driveway leads to the garage, providing ample parking space. Large windows allow natural light to enter the living spaces.
Home in Clarksdale
4.72 out of 5 average rating, 181 reviews

Down Home Southern Charmer

This is the home that my sister and I grew up in with our parents and younger brother, who have passed on. We love our home, and are now opening it up to guests from anywhere in the world who want a comfortable place to stay while visiting the Mississippi Delta. Available to our guests are a centrally heated and cooled home with two bedrooms, a living/dining room, a family room with TV and Internet, two bathrooms, a kitchen, washer and dryer, and a garage. And, we just put in new floors!

Guest favourite
A cozy living area features two light-colored sofas opposite each other, adorned with decorative pillows. An intricate area rug covers the floor, complementing the rustic wooden walls and high ceiling. A room divider is positioned in the background, dividing the space from the bedroom. Natural light filters through the nearby windows.
Cottage in Clarksdale
4.91 out of 5 average rating, 322 reviews

Sunflower Cottage on the River

Only a mile from historic home of the blues, Clarksdale in a gated community. The cottage sits on the banks of the Sunflower River with beautiful views of rustic woods. Out your window you might see deer, fox & other wildlife. Take a walk along the riverbank. You’ll enjoy relaxing in the comfy beds, ,enjoy privacy, the piano , & closeness to all the blues music venues. It has two fire pits, an outside grill & full kitchen. Great for couples, adventurers, business travelers , musicians ,

Guest favourite
A charming blue cottage features a gabled roof and a white front door framed by two light fixtures. Two vintage chairs are positioned on the grassy area in front, surrounded by mature trees that provide some shade.
Cottage in Clarksdale
4.82 out of 5 average rating, 177 reviews

The Gallery at Chateau Debris

Welcome to The Gallery! This one-bedroom cottage sits behind the main house. It has recently been renovated, but is decorated with vintage furnishings for personality. The cottage is equipped with a full kitchen, bedroom, bathroom, washer and dryer, & Roku TV. Your stay will be unique, as the decor has been selected from my collector's lair, and the best part is - it's all for sale! The Gallery is a live-in collectibles showroom so, contrary to the saying - you CAN take it with you!

Guest favourite
A charming cottage is set in a lush green landscape, featuring a wooden porch with seating. The exterior showcases light wood siding and large windows that allow natural light to fill the space. Surrounding trees create a serene atmosphere.
Farm stay in Shaw
4.94 out of 5 average rating, 354 reviews

Peacock in the Delta/ Mississippi Delta Cottage

WELCOME TO PEACOCK-A charming cottage set on a 1,700 acre bucolic farm in the middle of the Mississippi Delta. Private and secure. All guests are welcome to use the swimming pool (June 1-October 2), tennis court, horseback riding, walking trails. We are perfectly located in the middle of the Delta, with close proximity to most blues trail sites. We are also within easy driving distance to most restaurants in the Delta. Need more space? See https://abnb.me/ERkRyvI0rjb

Guest favourite
An exterior view of the restored shotgun shack is presented, featuring rustic wooden siding and a metal roof. Steps lead to the entrance, and a small porch is visible. The surrounding grassy area is open, complementing the rural ambiance.
Cabin in Benoit
4.92 out of 5 average rating, 216 reviews

The Shotgun Shack ❤️ of MS Delta

This Shotgun Shack is a genuine cypress board and batten shotgun shack. Construction of the cabin dates back to the late 1920’s, after the Great Flood of 1927. The shack was move to the property and has undergone a complete restoration. It has all the amenities needed for a comfortable stay. Situated behind the antebellum Burrus Home a.k.a “The Baby Doll House”, near Benoit, MS. There is a gas station in Benoit that sells beverages and snacks but no grocery stores.

Top guest favourite
A single-story guest house features a well-maintained, grassy lawn. The front facade includes multiple large windows and a landscaped area with shrubs and trees. A wide driveway leads up to the entrance, providing easy access to the home.
Guest suite in Cleveland
4.97 out of 5 average rating, 264 reviews

The Honnoll's "High Cotton" Guesthouse

This cozy guest house is the perfect place for your stay in Cleveland, MS, the heart of the Mississippi Delta! It is easy walking distance to the Cleveland Country Club and a five minute drive (or less!) to everywhere in town, including the new Grammy Museum, the Downtown shopping area, and the Delta State Campus and Football Stadium! There are Uber and a local taxi company for transportation. We look forward to seeing ya'll!

Top guest favourite
A red barn-style structure is shown with a newly constructed wooden deck and stairs leading to an upper level. Lush green grass surrounds the base, and shaded areas are created by trees in the background under a clear blue sky.
Farm stay in Indianola
4.96 out of 5 average rating, 100 reviews

Rustic Apartment in Indianola, MS

Welcome to the Farm! A rustic apartment located on the Sunflower River. The apartment over looks our cow pastures. Other animals you might see are horses, chickens and goats. The newly redone deck with be a great spot to watch the sun set in the evenings. We are just a few miles south of the B.B. King museum and a short drives to many other blues trail spots. We also welcome Hunters looking for those Delta Ducks.

Guest favourite
A cozy room featuring a queen bed with white linens and blue accent pillows. Nightstands with lamps are placed on either side, and a mirror reflects the softly lit interior. The private bathroom is visible through an open door, equipped with essential toiletries.
Cottage in Lake Village
4.83 out of 5 average rating, 122 reviews

Peaceful cabin in orchard! Great Internet!

The Betty suite cabin is based on a standard hotel room. We have a queen bed, microwave, mini-fridge, and coffee pot. The private bathroom include a large shower with shampoo, conditioner, and body wash. Each room has high-speed Internet with a flat screen, smart TV. This building was the original home of our neighbors - Earl and Betty. We moved the structure to the park and turned it into 2 hotel suites.

Top guest favourite
The brick exterior of Blues Hound Flat is characterized by large glass block windows and a centrally positioned red door. Horizontal blinds cover the windows, providing a sense of privacy while allowing light to filter through. A small air conditioning unit is visible above the door.
Loft in Clarksdale
4.93 out of 5 average rating, 451 reviews

Blues Hound Flat

Blues Hound Flat sits quietly across from the historic Greyhound bus station in the center of downtown Clarksdale. Step outside, and you're in the heart of the Delta Blues, surrounded by local eateries, shops, bars, and music venues! The air itself is heavy with the traditions of the Delta. This loft-style flat features all the basic amenities one could want and solitude when needed.

Top guest favourite
The spacious bedroom features a large bed with an ornate headboard and coordinating furnishings. A wooden dresser is positioned against a wall, while two comfortable leather chairs and an end table create a cozy seating area. Natural light enters through a nearby window.
Home in Cleveland
4.84 out of 5 average rating, 143 reviews

Comfortable Spacious Home Sleeps Up To 16 w/pool

This is a spacious, 2-story home with 7 bedrooms, 4 baths, family room, large kitchen, large dining room, and in-ground pool. The property is 5 to 10 minutes from DSU, Grammy Museum, and restaurants. EVENTS ARE NOT ALLOWED! Guests cannot have class reunions, family reunions, weddings, receptions, large gatherings before or after funerals, etc.). Property has perimeter cameras.

Popular amenities for Cleveland holiday rentals

When is the best time to visit Cleveland?

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Avg. price$146 SGD$164 SGD$152 SGD$146 SGD$155 SGD$148 SGD$158 SGD$168 SGD$148 SGD$178 SGD$177 SGD$189 SGD
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Frequently Asked Questions

  • Do house rentals in Cleveland have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Cleveland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cleveland have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Cleveland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Cleveland?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly house rentals in Cleveland?

    Cleveland has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Cleveland?

    Experience the best of Cleveland with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Cleveland have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Cleveland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cleveland have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Cleveland. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Cleveland?

    Yes! Work meets play with ease at over 10 vacation rentals in Cleveland featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about holiday rentals in Cleveland

  • Total holiday rentals

    Explore 20 holiday rentals in Cleveland

  • Nightly prices starting at

    Cleveland holiday rentals start at $101 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,300 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    20 of Cleveland holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cleveland rentals

  • 4.8 Average rating

    Cleveland stays are highly rated by guests – averaging 4.8 out of 5!

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