Vacation rentals in Cleveland

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Top-rated vacation rentals in Cleveland

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

Guest favorite
Apartment in Clarksdale
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.
Nov 20 – 27
$125 per night
4.93 out of 5 average rating, 152 reviews
Guest favorite
Home in Cleveland
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 a 16 camera surveillance system (14 outside and 2 inside—1 in family room and 1 in sunroom). Cameras are not in bedrooms and bathrooms.
Dec 28 – Jan 4
$342 per night
4.8 out of 5 average rating, 110 reviews
Guest favorite
Guesthouse in Cleveland
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!
Mar 28 – Apr 4
$86 per night
5.0 out of 5 average rating, 17 reviews

Popular amenities for Cleveland vacation rentals

Stay near Cleveland's top sights

Hey Joe's Burgers + Beer8 locals recommend
GRAMMY Museum Mississippi9 locals recommend
Kroger9 locals recommend

Other great vacation rentals in Cleveland

Guest favorite
Loft in Clarksdale
Delta Sunset Lofts - Historic 1910 Synagogue Apt C
Sep 6 – 13
$93 per night
4.98 out of 5 average rating, 44 reviews
Guest favorite
Home in Greenville
The Beehive
May 7 – 14
$106 per night
4.92 out of 5 average rating, 12 reviews
Guest favorite
Home in Leland
Pink on the Creek Guest House
May 13 – 20
$161 per night
4.97 out of 5 average rating, 73 reviews
Guest favorite
Cottage in Greenville
Beautiful four bedroom lake cottage!
Feb 15 – 22
$254 per night
4.98 out of 5 average rating, 49 reviews
Guest favorite
Home in Clarksdale
Delta Dream Retreat (Entire Home)
Aug 3 – 10
$168 per night
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Tutwiler
Mississippi Delta Family Getaway
May 18 – 25
$138 per night
4.88 out of 5 average rating, 41 reviews
Guest favorite
Home in Greenville
The Overlook at Bachelor Bend on Lake Ferguson
Nov 22 – 29
$302 per night
5.0 out of 5 average rating, 10 reviews
Guest favorite
Guesthouse in Clarksdale
Honey Hill Carriage House
Jun 23 – 30
$48 per night
4.91 out of 5 average rating, 46 reviews
Guest favorite
Home in Clarksdale
Rusty's Roost
Jul 24 – 31
$135 per night
4.83 out of 5 average rating, 24 reviews
Guest favorite
Cabin in Lake Village
Water's Edge Oasis
Feb 9 – 16
$148 per night
4.96 out of 5 average rating, 92 reviews
Guest favorite
Cabin in Chatham
Cabin on the Lake
Dec 19 – 26
$106 per night
5.0 out of 5 average rating, 7 reviews
Guest favorite
Villa in Clarksdale
The Governor's Mansion - A Step Back in Time.
May 14 – 21
$642 per night
5.0 out of 5 average rating, 12 reviews

Quick stats about vacation rentals in Cleveland

Total rentals

20 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

20 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

930 reviews

Nightly prices starting at

$70 before taxes and fees

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 wifi, over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Cleveland?

    Cleveland has more than 10 family-friendly stays. 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 $80 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Mississippi
  4. Bolivar County
  5. Cleveland