
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.

The Squeeze Box-"get your Blues on"
LOCATION-LOCATION-LOCATION The Squeeze Box is a spacious, airy 425 sq. ft. private vacation apartment, located in the heart of Historic Downtown Clarksdale, Mississippi. The newly constructed apartment is located on the ground floor of the former Clarksdale Telegraph Building (Circa 1897) @ the corner of Second & Delta in the Historic Blues District. Located across the street from the Hambone Art Gallery, and the “Rock & Blues Museum”, this is the best location in town. Gift shops around the corner. Restaurants including The Stone Pony, Yazoo Pass, Levon's Bar and Grill, and Grandma's House of Pancakes are literally all within 300 feet of our front door. CatHead Blues, Lambfish Gallery, and Hambone Gallery are all on our block. The Delta Blues Museum is a short walk, and Ground Zero Blues Club, New Roxy and Red’s Lounge are an easy 5-minute stroll. The Squeeze Box is the best location in Clarksdale for walkable access to restaurants, music venues, museums,bars, clubs,art galleries,shopping on Delta,convenience store,and the wine & spirits store. No need to drive once you check in.....park your car, and party to your heart's content. And The Squeeze Box is located on the ground floor, so there are no stairways to climb or drag your bags up. And we have a covered veranda out front with seating for six,so you can enjoy the fresh air, while enjoying a nice beverage. Although there is no smoking allowed in the apartment, the veranda is just outside your door. Available by the night,weekends, and weekly. Inquire about longer stays.

Pink on the Creek Guest House
No cleaning fee! Rate is up to 4 people. 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 on beds & closet . Your comfort is our priority.

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!

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!

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

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.

The Sunflower Penthouse on the River in Clarksdale
Beautiful relaxing views highlight this upstairs luxury 700 sq ft apartment in a gated community , only one mile from Clarksdale MS. This 2 bedroom guest suite features a private, separate entrance , beautiful antiques , large 2 tiered deck with gas fire pit overlooking the banks of the Sunflower River. A cargo lift for luggage & stairs for guests, small kitchenette with sink, hot plate ,microwave mini fridge and toaster oven & large outside gas grill .

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!

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.

Beautiful luxurious 2 bedroom!
This luxury 2-bedroom home offers hardwood floors, an open-concept layout, and abundant natural light. The gourmet kitchen features quartz countertops, stovetop and a small dining space. Both bedrooms are furnished with plush queen beds and quality linens. Elegant crystal lighting is showcased throughout, adding sophistication and charm to every room, creating a warm and inviting upscale retreat.”

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.

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
Other great holiday rentals in Cleveland

Delta Sunset Lofts - Historic 1910 Synagogue Apt B

Nice Home and safe neighborhood!

Authentic Delta Bungalow in the Heart of Indianola

Delta Comfort

Home in The Woods

Country Ridge Pool and Resort

Sutton's Serenity Place

Serenity Retreat
When is the best time to visit Cleveland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 100 | € 112 | € 103 | € 100 | € 106 | € 101 | € 108 | € 115 | € 101 | € 142 | € 115 | € 97 |
| Avg. temp | 7°C | 9°C | 13°C | 18°C | 23°C | 26°C | 28°C | 28°C | 24°C | 18°C | 12°C | 8°C |
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 free parking, over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, 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 € 69 per night before taxes and fees

Verified guest reviews
Over 1,250 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

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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