
Holiday rentals in Cleveland
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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 £61 per night before taxes and fees

Verified guest reviews
Over 1,390 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!
Top-rated holiday rentals in Cleveland
Guests agree: these stays are highly rated for location, cleanliness and more.

“Pink on the Creek”Guest House
Longer stay discounts . ONLY ONE PET ALLOWED. (Pet fee). 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. people love it. Very Affordable for a whole house in this area. A selection of pillows.

Cozy Country Pool House Retreat
Our cozy pool house retreat is located in the Heart of the Mississippi Delta on a secluded 40 acre country setting surrounded by woods and a beautiful bayou full of cypress trees. It's located just off Drew-Merigold Road away from everyone, with no neighbors!! Yet close to everything - only 5 minutes to Drew, 10 minutes to Ruleville, 15 minutes to Cleveland, and 30 minutes to Clarksdale. We are only 10 minutes to McCarty's Pottery in Merigold, and 15 minutes to Peter's Pottery In Mound Bayou.

Country Ridge Pool and Resort
This place provides Comfortability, very spacious, private rooms, sitting where everyone can come together for meetings, No Parties over 15 people and Only the ppl that on list are allowed at this home.. No Big events allowed.. No Pool Parties and No outdoor activities that include outside guests.. There is a Park for your children that are on the guest list only...Patio space, barbecuing area and experience fun time with guests and family for those on the list.. No outsiders are included..

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!

The Delta Cottage
Newly renovated large home located in an upscale neighborhood in Cleveland, MS: 3 bedrooms (1 King, 1 Queen & 3 Twin beds), 2 bathrooms, living room, formal dining room, eat-in kitchen with bay window seating, laundry room, spacious foyer, all-season enclosed patio, extended driveway, 2-car garage, and large outdoor space. We are centrally located to Delta State University, the Grammy Museum, restaurants, Delta Pecan Company Orchard & steps away from the historic Mississippi Blues Trail.

Delta Vibes & Modern Comfort in Cleveland, Ms.
Have fun with the whole family and Experience the best of Cleveland, MS in this stylish modern home located just minutes from Delta State University, the Grammy Museum, and downtown’s vibrant music, dining, and festival scene. Perfect for game days, concert weekends, or relaxing Delta getaways. Enjoy comfortable living spaces, a fully equipped kitchen, and a peaceful neighborhood setting while staying close to everything that makes Cleveland one of Mississippi’s most exciting small towns.

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 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!

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.

Water's Edge Oasis
Water's Edge Oasis puts you right in the middle of the Arkansas Delta, minutes from the Mississippi River, close to Greenville, MS, and surrounded by great fishing and hunting. The cabin sleeps four, with two bedrooms, a full kitchen, air conditioning, washer, and free parking on-site. It's a comfortable, simple space built for people who came to enjoy the great outdoors.

The Delta House
Step back in time with this Historic Delta home. Built in 1906, this 4 BR, 4 Bath home is tastefully appointed and centrally located. 2 blocks from the Grammy Museum and Delta State University and 1/4 mile from Cotton Row and Downtown Cleveland its the perfect place to start your stay in the Heart of the Delta.
Popular amenities for Cleveland holiday rentals
Other great holiday rentals in Cleveland

🌺Lillie's Manor🌺

Kozy Komfort LLC

Dollie’s Cove #2

Swamp Station · A Tiny Train Car Guest House

Spacious Hideaway | 5 bds, 3 ba

Three bedroom home with one and a half bath

Greenville's Green Historic Stay Hosted by T&M

Serenity Retreat
When is the best time to visit Cleveland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £114 | £107 | £114 | £88 | £93 | £89 | £95 | £101 | £89 | £107 | £106 | £114 |
| 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
What are the best places to stay in Cleveland?
Downtown Cleveland is frequently suggested for a stay near shops, dining, and cultural sites. Residential neighborhoods around the town offer homes with more space, often welcoming to families and groups.
What are the best things to do in Cleveland with kids?
Families frequently explore hands-on exhibits at the GRAMMY Museum Mississippi, visit local parks, or catch a family performance at the Bologna Performing Arts Center. Art walks and outdoor play spaces offer activities for all ages.
What are some of the best things to do in Cleveland?
Explore the GRAMMY Museum Mississippi, stroll through downtown’s art installations and shops, or attend a performance at the Bologna Performing Arts Center. Locally owned restaurants and outdoor spaces add to the area’s appeal.
How is the weather in Cleveland?
Cleveland has mild, wet winters near 35–55°F (2–13°C), and warm, humid summers reaching 89–92°F (32–34°C). Spring and autumn are often comfortable for outdoor activities, though rainfall remains steady throughout the year.
When is the best time to visit Cleveland?
Spring and autumn are often recommended for visiting Cleveland, as temperatures are comfortable for walking and outdoor events. These seasons highlight local gardens, festivals, and community activities.
What are the best places to visit in Cleveland?
Explore the GRAMMY Museum Mississippi, the Bologna Performing Arts Center, and the Mississippi Delta’s distinctive local shops and art galleries. The downtown area is often recommended for a sense of Cleveland’s culture and creativity.
What are some hiking trails in Cleveland?
You can find walking or nature trails in parks around Cleveland, with features like ponds, picnic areas, and shaded paths. For more immersive outdoor experiences, explore nearby nature preserves or recreational areas.
What are some family activities we can do in Cleveland?
Families enjoy interactive exhibits at the GRAMMY Museum Mississippi, outdoor play in local parks, and ice cream shops around Cleveland. Community art events and seasonal festivals often include family-friendly activities and crafts.
What are some of the best day trip ideas from Cleveland?
Plan a day exploring historic sites, visit a museum highlighting blues music heritage, or enjoy time at a nearby state park. Small towns around Cleveland often host festivals, markets, or tours connected to Delta culture and history.
Are there any pet friendly accommodations available in Cleveland?
Pet friendly accommodations can be found in Cleveland, with many stays welcoming dogs and cats. Neighborhoods with local parks or walking paths make it easier to explore with your pet.
What are some local tips for visiting Cleveland?
Try authentic Delta cuisine at locally rooted restaurants, visit during a festival for community energy, and bring layers as temperatures can shift throughout the day. Exploring art murals and chatting with shop owners reveal Cleveland’s creative spirit.
What is Cleveland known for?
Cleveland is known for its connections to blues music, vibrant arts scene, and Mississippi Delta cuisine. The city’s museums, performing arts centers, and locally owned shops reflect its creative and musical heritage.
What are the best hidden gems to explore in Cleveland?
Browse local art galleries, discover murals that share community stories, or visit lesser-known coffee shops and bookstores around Cleveland’s downtown. Small music venues or pop-up markets are often favorites among locals.
What are the best foods to try in Cleveland?
Try dishes rooted in Delta traditions such as barbecue, fried catfish, and locally made tamales. Seasonal pies and classic Southern sides are also frequently suggested for a taste of the region.
What should I bring for a trip to Cleveland?
Pack layers for changing temperatures, comfortable shoes for exploring on foot, and a rain jacket since showers are common year-round. If you plan to visit local events or trails, a camera and outdoor essentials can be helpful.
What is the nightlife in Cleveland like?
Cleveland has a relaxed nightlife scene centered around local bars, live music venues, and restaurants. Many visitors explore downtown spots known for casual gatherings and Southern hospitality.
What are the most popular events or festivals in Cleveland?
Cleveland is known for music and cultural events, often anchored in the blues tradition and seasonal celebrations. Events connected to the arts, food, or community gatherings are frequently suggested throughout the year.
Are there family friendly vacation rentals in Cleveland?
Cleveland has a variety of family friendly vacation rentals, including homes and apartments with multiple bedrooms, kitchens, and flexible spaces. Many neighborhoods are known for a welcoming, residential feel.
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