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Cleveland Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Cleveland holiday rentals

Living area

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (18 reviews)
"The location was amazing and the place is really nice! Absolutely love that it is dog friendly and the host is really responsive! We will definitely be staying again! "
United States
Emily G.
The price is HK$1,023
HK$1,765 total
includes taxes & fees
22 Jun - 23 Jun
2nd floor loft near the lake!
Interior

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
3.0 star property
Two Rivers
The price is HK$1,199
HK$3,479 total
includes taxes & fees
1 Jul - 2 Jul
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
1 bedroom, WiFi

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.8 out of 10, Exceptional, (26 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is HK$744
HK$1,023 total
includes taxes & fees
21 Jun - 22 Jun
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
3 bedrooms, iron/ironing board, travel cot, WiFi

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"We are moving to Sheboygan and just needed a place for the 3 of to stay while we got the lay off the land. It was a clean and surprisingly roomy place. Thanks again for the hospitality!"
United States
Woomy B.
The price is HK$973
HK$1,647 total
includes taxes & fees
22 Jun - 23 Jun
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Lobby

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,043 reviews)
"Will remember to stay there again."
United States
Sonia
The price is HK$1,622
HK$1,841 total
includes taxes & fees
21 Jun - 22 Jun
Grandstay Residential Suites Hotel - Sheboygan
Interior

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.0 out of 10, Wonderful, (6 reviews)
"Great place to stay."
United States
Melissa B.
The price is HK$1,073
HK$3,566 total
includes taxes & fees
1 Jul - 2 Jul
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Exterior

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (5 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is HK$987
HK$2,704 total
includes taxes & fees
23 Jun - 24 Jun
Logan Ave Holiday House - Upper
TV

Apartment Centrally Located

Apartment Centrally Located
Plymouth
10.0 out of 10, Exceptional, (2 reviews)
"Convenient location in between Road America, Elkhart Lake, and Plymouth. You're about 10 minutes from everything you stay in the area for.The apartment is a dorm, but it's clean and quiet and was perfect for spending our nights while watching the races at Road America."
United States
Brian H.
The price is HK$1,081
HK$1,680 total
includes taxes & fees
30 Jun - 1 Jul
Apartment Centrally Located
Dining

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"We came for a girl's weekend and the house was perfect for us. The location is great (walking distance to town), the house was clean and we appreciated having the well stocked kitchen. I would definitely stay again!"
United States
Cinda Z.
The price is HK$1,199
HK$2,570 total
includes taxes & fees
30 Jun - 1 Jul
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Fridge, microwave, oven, stovetop

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (42 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is HK$1,058
HK$3,202 total
includes taxes & fees
23 Jun - 24 Jun
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
TV

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
The price is HK$1,073
HK$3,272 total
includes taxes & fees
21 Jun - 22 Jun
Large Backyard, Walk to Hospital: Sheboygan Abode!
Interior

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is HK$1,199
HK$3,208 total
includes taxes & fees
21 Jun - 22 Jun
Large Backyard, Walk to Hospital: Sheboygan Abode!
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (60 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is HK$1,559
HK$2,133 total
includes taxes & fees
24 Jun - 25 Jun
The Esker Ridge Chalet, Pristine Elkhart Solitude
Fridge, microwave, oven, stovetop

The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (8 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
The price is HK$1,857
HK$4,954 total
includes taxes & fees
22 Jun - 23 Jun
The Links! - Luxury Golf Retreat with Golf Simulator
Exterior detail

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New Holstein
10.0 out of 10, Exceptional, (175 reviews)
"Great place would go back"
United States
William
The price is HK$1,587
HK$2,625 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Smart TV

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Sheboygan
9.8 out of 10, Exceptional, (16 reviews)
"Welcoming and attentive hosts with helpful recommendations, clean and cozy space. "
United States
Brenda R.
The price is HK$2,029
HK$3,246 total
includes taxes & fees
30 Jun - 1 Jul
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Interior

ADA Accessible Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens – Unit #1

ADA Accessible Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens – Unit #1
Brillion
10.0 out of 10, Exceptional, (1 review)
"Did not need we were visiting family near by"
United States
Cathy G.
The price is HK$1,481
HK$2,334 total
includes taxes & fees
21 Jun - 22 Jun
ADA Accessible Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens – Unit #1
Private kitchen

The Historic Downtown Suite

The Historic Downtown Suite
Sheboygan Falls
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely wonderful experiencethis place is darling!!!! We will be staying here again"
United States
Kristin E.
The price is HK$1,191
HK$1,991 total
includes taxes & fees
13 Jul - 14 Jul
The Historic Downtown Suite
Smart TV, books

*NEW* Beautiful & Convenient!

*NEW* Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (20 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is HK$1,347
HK$3,263 total
includes taxes & fees
25 Jun - 26 Jun
*NEW* Beautiful & Convenient!
Interior

Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is HK$1,135
HK$3,281 total
includes taxes & fees
22 Jun - 23 Jun
Sleeps 8 & Spacious!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cleveland Hotel Reviews

Watershed Hotel

Watershed Hotel

10/10 Excellent
"Big rooms, nice staff, good breakfast"
ANDREW 2-night trip
Posted 4 hours ago
Watershed Hotel

Find out more about Cleveland

Search for holiday rentals in Cleveland on Expedia! You can easily find your home rentals, villas, holiday apartments in Cleveland using one of the methods below:

  • View our selection of featured holiday rentals in Cleveland
  • Use the map to find apartments and other holiday homes in the Cleveland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cleveland while they last

Look no further and take a look at our great range of rental properties in Cleveland!

Frequently asked questions

Can I find a holiday rental in Cleveland?

Yes, there are holiday rentals close to the most popular sights in Cleveland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cleveland has to offer?

Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room: This holiday home rental outside of Cleveland is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

How many holiday rentals are there in Cleveland?

Expedia has 12 holiday rentals for your stay in Cleveland.

What can I see and do in Cleveland?

Lake Michigan and Dairyland Park are a couple of lovely local spots to get outside and enjoy nature. While here, Veterans Memorial Park and Hika Bay are other places worth a visit.

What are holiday rentals like in Cleveland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cleveland. Holiday rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.