Vacation rentals in Cleveland

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Top-rated vacation rentals in Cleveland

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Guest favorite

Apartment in Clarksdale

4.93 out of 5 average rating, 152 reviews

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.

Jul 29 – Aug 5

$125 per night

Guest favorite

Home in Cleveland

4.8 out of 5 average rating, 112 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 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.

Jul 31 – Aug 7

$342 per night

Guest favorite

Guesthouse in Cleveland

5.0 out of 5 average rating, 18 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!

May 2 – 9

$86 per night

Guest favorite

Cottage in Clarksdale

4.92 out of 5 average rating, 285 reviews

Sunflower Cottage on the River

Only a mile from historic home of the blues, Clarksdale. 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 love to relax in the comfy beds, take in the great views, enjoy privacy, & closeness to all the blues music venues. It has two fire pits, an outside grill & full kitchen. Great for couples, adventurers, business travelers & perfect writer's escape.

Sep 14 – 21

$124 per night

Superhost

Cottage in Clarksdale

4.81 out of 5 average rating, 123 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!

Nov 30 – Dec 7

$90 per night

Guest favorite

Home in Cleveland

4.93 out of 5 average rating, 30 reviews

Relaxing Home in Quiet Location

Our home is warm and inviting with an open floor plan living room, dining room and kitchen area with window views all around, fireplace and cozy decor. All bedrooms are nicely sized and have sunlight darkening drapes if you like to sleep in late. There are two full bathrooms both have a shower and bath, one bathroom is in the master bedroom. Double car garage and large fenced in backyard with a grill, fire pit, couch, chairs, and kids play-set available to you when you stay.

Jul 9 – 14

$374 per night

Guest favorite

Farm stay in Shaw

4.94 out of 5 average rating, 309 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

Jul 19 – 26

$106 per night

Guest favorite

Home in Greenville

4.93 out of 5 average rating, 105 reviews

🌞 A Ray of Sunshine 🌞

Enjoy a ray of sunshine in this gorgeous 3 bedroom, 1 bathroom home with garage access for private parking. This home consists of two spacious bedrooms with queen size beds in both rooms. There is also a third smaller room with a twin size bed. Three smart TVs with accessible WiFi and one HD TV with DirecTV in the living room area. Alarm system available for guests as well. Check in instructions will be sent 1-2 days prior to checking in. 🚭No smoking 🚫No Pets

Jun 27 – Jul 4

$119 per night

Guest favorite

Guest suite in Cleveland

4.97 out of 5 average rating, 228 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!

Jun 27 – Jul 4

$92 per night

Guest favorite

Farm stay in Indianola

4.97 out of 5 average rating, 77 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.

Sep 3 – 10

$71 per night

Guest favorite

Guesthouse in Cleveland

4.91 out of 5 average rating, 43 reviews

Delta Guest House

Lovely, full-1 bedroom- 1 bathroom-private guest house. Has its own little covered porch. Parking along street. Located in a quiet neighborhood. Within walking distance or 2 min drive of DSU! Close by (less than 5min drive to most anywhere) you’ll find several parks, the Grammy Museum, bowling, skating, some of the best restaurants, a brand new laundromat, and our beautiful downtown Cleveland!

May 18 – 25

$70 per night

Guest favorite

Loft in Clarksdale

4.93 out of 5 average rating, 343 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.

Jul 10 – 17

$88 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cleveland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Superhost

Home in Tutwiler

4.88 out of 5 average rating, 41 reviews

Mississippi Delta Family Getaway

Feb 16 – 23

$138 per night

Guest favorite

Loft in Clarksdale

4.86 out of 5 average rating, 49 reviews

Delta Sunset Lofts - Historic 1910 Synagogue Apt A

Apr 22 – 29

$123 per night

Guest favorite

Cabin in Lake Village

4.96 out of 5 average rating, 97 reviews

Water's Edge Oasis

Jun 5 – 12

$148 per night

Guest favorite

Cottage in Greenville

4.98 out of 5 average rating, 52 reviews

Beautiful four bedroom lake cottage!

Feb 19 – 26

$250 per night

Guest favorite

Home in Leland

4.97 out of 5 average rating, 76 reviews

Pink on the Creek Guest House

Jun 21 – 28

$161 per night

Superhost

Home in Greenwood

4.91 out of 5 average rating, 11 reviews

The Comm-Unity House 1

May 20 – 27

$85 per night

Guest favorite

Home in Clarksdale

4.85 out of 5 average rating, 26 reviews

Rusty's Roost

Sep 11 – 18

$135 per night

Guest favorite

Guesthouse in Clarksdale

4.92 out of 5 average rating, 50 reviews

Honey Hill Carriage House

Jan 22 – 29

$90 per night

Show all

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
970 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 a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, 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.

Vacation rentals in Cleveland

Top-rated vacation rentals in Cleveland

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Cleveland vacation rentals

Stay near Cleveland's top sights

Other great vacation rentals in Cleveland

Home in Tutwiler

Loft in Clarksdale

Cabin in Lake Village

Cottage in Greenville

Home in Leland

Home in Greenwood

Home in Clarksdale

Guesthouse in Clarksdale

Quick stats about vacation rentals in Cleveland

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Cleveland have free parking?

Do house rentals in Cleveland have air conditioning?

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

Are there family-friendly vacation rentals in Cleveland?

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

Do house rentals in Cleveland have wifi?

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