A rocky shoreline with waves crashing against the rocks and a large weeping willow tree in the background.

Cleveland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Cleveland vacation rentals

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1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,085 reviews)
"Nice place and good breakfast"
United States
Kristin
$125 nightly
The price is $142
Sep 27 - Sep 28
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
1 bedroom, WiFi

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.6 out of 10, Exceptional, (33 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
$103 nightly
The price is $117
Sep 17 - Sep 18
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
3 bedrooms, desk, iron/ironing board, travel crib

3. 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
9.8 out of 10, Exceptional, (10 reviews)
"Close to everything we were looking to do while visiting the area. Great communication and hospitality from host, would stay again!!"
United States
Heidi
$161 nightly
The price is $182
Sep 22 - Sep 23
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Interior

4. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (29 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
$332 nightly
The price is $377
Sep 14 - Sep 15
Total with taxes and fees
Sleeps 8 & Spacious!
Exterior

5. Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.4 out of 10, Exceptional, (28 reviews)
"This place is my spring spiritual reset. We’ll equipped, comfortable and serene. I had a lovely stay and hope to return next year"
United States
Kristine D.
$757 nightly
The price is $799
Sep 15 - Sep 16
Total with taxes and fees
Lake Michigan Beachfront - King Suite - Game Room
Living area

6. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (24 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.
$192 nightly
The price is $218
Sep 14 - Sep 15
Total with taxes and fees
2nd floor loft near the lake!
Smart TV, books

7. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (22 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
$295 nightly
The price is $335
Sep 22 - Sep 23
Total with taxes and fees
Beautiful & Convenient!
Dining

8. 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
9.8 out of 10, Exceptional, (29 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
$231 nightly
The price is $262
Sep 27 - Sep 28
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Interior

9. Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.4 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
$181 nightly
The price is $205
Sep 22 - Sep 23
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Exterior

10. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
$329 nightly
The price is $373
Oct 13 - Oct 14
Total with taxes and fees
Logan Ave Holiday House - Upper
Dining

11. Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Sheboygan
10.0 out of 10, Exceptional, (8 reviews)
"The house was great! It had everything we needed, was very clean, and cozy. We enjoyed our stay and Ginger was welcoming, available, and responsive. "
United States
Christine P.
$207 nightly
The price is $234
Sep 22 - Sep 23
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Coffee/tea maker, fridge, microwave, oven

12. The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (13 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
$554 nightly
The price is $629
Sep 27 - Sep 28
Total with taxes and fees
The Links! - Luxury Golf Retreat with Golf Simulator
Coffee/tea maker, fridge, microwave, oven

13. 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)
"Many extras that we have never seen at other rentals.Children's toys, beach toys, dog extras- leash dog bowls towels and a new toy to bring home. Walking distance to Lake Michigan. Restaurants that are 5 min distance driving. Kohler Andrae 15 min away! Kitchen had every item you would need.Hope to say again. Thanks for a great experience"
United States
Anonymous traveler
$374 nightly
The price is $424
Sep 22 - Sep 23
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Interior

14. Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
$188 nightly
The price is $213
Sep 22 - Sep 23
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Bar (on property)

15. Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
$644 nightly
The price is $706
Oct 1 - Oct 2
Total with taxes and fees
Victorian Inn Elkhart Lake Wisconsin
Interior

16. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
$222 nightly
The price is $252
Sep 22 - Sep 23
Total with taxes and fees
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Iron/ironing board, WiFi, bed sheets

17. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
$155 nightly
The price is $175
Sep 13 - Sep 14
Total with taxes and fees
Victorian Inn #241 | 2 Queen Beds
House (3 Bedrooms) | Interior

18. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great, very convenient to Road America."
United States
Kelis
$377 nightly
The price is $397
Sep 20 - Sep 21
Total with taxes and fees
Updated Plymouth Home ~ 5 Mi to Road America!
Coffee/tea maker, fridge, microwave, stovetop

19. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"This house was an excellent choice for our race weekend at Road America. It was very clean, the bedrooms were comfortable, check-in was easy, the neighborhood was quiet, and the proximity to the race track was great. Would definitely stay again!"
United States
Patricia V.
$386 nightly
The price is $407
Sep 20 - Sep 21
Total with taxes and fees
Updated Plymouth Home ~ 5 Mi to Road America!
Exterior

20. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (69 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
$247 nightly
The price is $261
Sep 15 - Sep 16
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
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
"This is a beautiful hotel with great staff!"
Andrea 1-night trip
Posted 22 hours ago
Watershed Hotel

Find out more about Cleveland

Everything you need to know about Cleveland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cleveland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cleveland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cleveland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cleveland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cleveland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $142 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cleveland rentals

At Expedia, we put the best Cleveland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cleveland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cleveland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cleveland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Cleveland?

Yes, we give you a choice of vacation rentals close to popular sights in Cleveland, or you can go with a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Cleveland?

Insane luxury beachfront estate - complete with indoor pool, arcade and theater!: Visitors like this Cleveland vacation home rental. It is located on a lake and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Cleveland?

Expedia has 11 vacation 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 vacation rentals like in Cleveland?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Cleveland. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.