Chesterland Holiday Rentals, Ohio: Private House Rentals

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Our top choices for Chesterland hotels

A modern lobby with a sectional sofa, ottomans, and a reception desk.

A modern living room with a sectional sofa, a wooden coffee table, and a flat-screen TV mounted on a brick wall.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a sunlit area with large windows.

A Drury Inn & Suites building with a modern design, featuring multiple floors, large windows, and a covered entrance area.

1. Drury Inn & Suites Cleveland Beachwood

Orange

Robert

3.185.891 ₫

3.743.423 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A modern hotel with a glass facade, multiple floors, and a covered entrance area.

A bar area with a long counter, multiple bar stools, and a coffee machine.

A modern lobby with a reception desk, seating area, and a staircase.

An indoor swimming pool with clear blue water, sunlit by large windows, surrounded by lounge chairs and exercise equipment.

2. Hyatt Place Cleveland/Lyndhurst/Legacy Village

Lyndhurst

Evelyn

3.760.704 ₫

4.418.828 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A modern office space with wooden tables and benches, a reception area, and large windows offering views.

A hotel room with a large bed, a television, a desk with a lamp, and a bookshelf.

A modern hotel lobby with wooden flooring, green and yellow chairs, a reception desk, and large windows offering a view of the outdoors.

A modern building entrance with a parking area, a sign for 'Spark', and a clear sky.

3. Spark by Hilton Cleveland Beachwood

Beachwood

Natalie

2.548.399 ₫

2.994.368 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A Holiday Inn Express & Suites building with a modern design, featuring a large entrance and a parking area.

A swimming pool with chairs and a reception desk.

A hotel room with a coffee machine, a bed, and a window with a view.

A buffet with labeled containers of omelets and other dishes.

4. Holiday Inn Express & Suites Painesville - Concord by IHG

Painesville

Sandra

2.872.760 ₫

3.310.854 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A hotel with a modern brick facade, a covered entrance, and landscaped areas with young trees.

A modern hotel lobby with two grey armchairs and a small yellow table.

An indoor swimming pool with a tiled edge, surrounded by green and yellow lounge chairs, and a view of the outdoors through large glass doors.

A hotel room with a large bed, a sofa, a TV, a desk with a lamp, and a window with curtains.

5. SpringHill Suites by Marriott Cleveland/Solon

Solon

Michael

3.529.577 ₫

4.147.253 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A bar area with a sign reading "Six Horses Tavern," shelves stocked with bottles, a bar counter, and multiple bar stools.

A spacious living room with a fireplace, a large sofa, a brown leather armchair, and a chandelier.

An indoor swimming pool with wooden beams, clear lanes, and a '3 FT NO DIVING' sign.

A bar area with a counter, stools, and a variety of bottles.

6. The Aurora - a Boutique Hotel

Aurora

KIMBERLY

2.350.440 ₫

2.655.997 ₫ total

includes taxes & fees

30 Aug - 31 Aug

An outdoor patio area with a fire pit, seating, and a pool visible through the glass enclosure.

A modern living room with a grey sofa, wooden side tables, a flat-screen TV mounted above a fireplace, and a yellow ottoman.

A modern hotel lobby with a large seating area, a bar, and a television screen.

A modern hotel room with a dining area, a sofa, a TV, and a fireplace.

7. Hampton Inn & Suites Cleveland-Beachwood

Orange

Mike

2.955.287 ₫

3.472.462 ₫ total

includes taxes & fees

20 Sept - 21 Sept

An outdoor patio with a fire pit, seating, and a grill.

A modern hotel with a prominent sign reading "TOWNEPLACE SUITES".

A bar area with a red counter, multiple bar stools, and a city skyline artwork on the wall.

An indoor swimming pool with clear glass walls, a patio area with tables and chairs, and a view of the outdoors.

8. TownePlace Suites by Marriott Cleveland Solon

Solon

Mellissa Marie

2.797.024 ₫

3.286.503 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A hotel with a central entrance, multiple windows, and a parking area with a car.

A hotel lobby with a stone fireplace, comfortable seating, a flat-screen TV, and a dining area.

An outdoor patio area with wicker furniture and a stone fireplace.

A modern hotel lobby with a long counter, seating area, and a buffet with various food items.

9. Staybridge Suites Cleveland Mayfield Heights Beachwood by IHG

Mayfield Heights

Lia

2.951.108 ₫

3.467.682 ₫ total

includes taxes & fees

31 Aug - 1 Sept

An outdoor patio with stone seating, a fire pit, and a pergola with string lights.

A spacious lobby with a fireplace, seating area, and a reception desk.

A multi-story hotel with a beige and red facade, a central entrance with a canopy, and a landscaped front yard with various shrubs and a tree.

A hot tub with a metal ladder, surrounded by teal walls and large windows.

10. Homewood Suites by Hilton Cleveland-Beachwood

Beachwood

Julie

3.619.155 ₫

4.252.508 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A Courtyard by Marriott hotel with a covered entrance, large windows, and a landscaped front area.

A modern kitchen with a curved island, bar stools, and a coffee station.

An outdoor patio with a fire pit, wicker chairs, and string lights.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

11. Courtyard by Marriott Cleveland Beachwood

Beachwood

Daljinder

2.846.644 ₫

3.344.807 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A spacious lobby with a reception desk, seating area, and decorative elements.

A spacious living area with sofas, a coffee table, and a bar area with stools.

A modern hotel lobby with a dining area, sofas, and a bar.

A swimming pool with a seating area, large windows, and potted plants.

12. Cleveland Marriott East

Warrensville Heights

Chi Yun

3.751.563 ₫

4.408.087 ₫ total

includes taxes & fees

30 Aug - 31 Aug

An outdoor seating area with a fire pit, wicker furniture, and string lights.

A modern kitchen with a built-in microwave, sink, and coffee maker.

A modern hotel with a covered entrance, large windows, and an American flag.

A modern hotel lobby with a green sofa, blue ottoman, and a wooden dining table.

13. Home2 Suites by Hilton Cleveland Beachwood

Beachwood

Larry

2.976.702 ₫

3.497.625 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A hotel reception area with a counter, seating area, and a wall with a mural.

A corner market with a Pepsi refrigerator, snack shelves, and a sign for the Corner Market.

A hotel room with a large bed, a bedside table with a lamp, a wall-mounted TV, and a separate bathroom with a bathtub.

A reception area with a wooden reception desk, blue chairs, a small table, and a colorful striped rug.

14. Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Streetsboro

rose

3.194.509 ₫

3.609.796 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A multi-level hotel lobby with a central pool, multiple seating areas, and large chandeliers.

A dining area with tables set for meals, a waiter in the background, and a child serving food to an adult.

A multi-level atrium with a glass ceiling, water features, and a central reception area.

A hotel lobby with a long dining table, multiple chairs, a reception desk, and a high ceiling with balconies.

15. Embassy Suites by Hilton Cleveland Beachwood

Beachwood

Yonah

3.190.853 ₫

3.749.252 ₫ total

includes taxes & fees

30 Aug - 31 Aug

An indoor swimming pool with a wooden ceiling, clear skylights, and a tiled floor.

A modern kitchen with white cabinets, a microwave, coffee maker, and a fruit bowl. There are yellow chairs and a table in the dining area.

A modern living room with a ceiling fan, large windows, and a blue patterned rug.

A hotel room with a large bed, two bedside tables, a nightstand, and a wall with a geometric pattern.

16. Comfort Inn Painesville - Concord

Painesville

Kristie

2.938.050 ₫

3.386.103 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A hotel lobby with two sofas, a coffee table, and a dining area with chairs and tables.

A hotel lobby with a curved glass wall, a 'Welcome' sign, and a seating area with patterned chairs and a table.

A restaurant with a curved glass roof, tables, chairs, and a flat-screen TV on the wall.

A hotel lobby with a dining area, sofas, and a large window offering a view of the outdoors.

17. Hampton Inn Cleveland-Solon

Solon

Evangeline

2.548.399 ₫

2.994.368 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A large, historic building with multiple windows and a well-maintained lawn.

An outdoor patio with wicker furniture and string lights.

A grand hallway with a large Christmas tree, elegant chandeliers, and a red carpet leading to a dining area.

A dining area with a Christmas tree, tables set for a meal, and large windows.

18. The Glidden House

University Circle

Sufia

3.973.549 ₫

4.668.919 ₫ total

includes taxes & fees

24 Aug - 25 Aug

A living room with a fireplace, a flat-screen TV mounted above it, striped armchairs, a small side table with a lamp, and a framed picture on the wall.

A hotel room with a living area, a dining area, a kitchenette, and a bedroom.

An indoor swimming pool with clear lane markings, lounge chairs, and a view of the cityscape through large windows.

A lobby with a fireplace, seating area, and a reception desk.

19. Holiday Inn Express Hotel & Suites Cleveland-Streetsboro by IHG

Streetsboro

Richard

3.421.196 ₫

3.865.951 ₫ total

includes taxes & fees

9 Sept - 10 Sept

A restaurant interior with wooden tables, black chairs, and orange walls.

A traditional hotel room with a desk, computer, and seating area.

A hotel sign with 'BW Best Western PLUS Inn & Suites' and 'Lawnfield' written on it.

20. Best Western Plus Mentor-Cleveland Northeast

Mentor

Tracy

3.085.605 ₫

3.556.159 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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Stay near popular Chesterland attractions

Fowler's Mill Golf Course

8.0/10 (1 review)

This Pete Dye masterpiece challenges golfers with three distinct nine-hole courses woven through natural landscapes. Test your strategy on the Lake nine's signature Coastline hole where precision trumps power.

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Berkshire Hill Golf Course

This former golf course wove through 240 acres of Ohio's natural hills, woods, and waterways. Players appreciated its strategic layout that balanced challenge with scenic tranquility.

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Chesterland City Park

Chesterland City Park offers baseball fields, pickleball courts, and family-friendly pavilions. Reserve one of two covered areas for a premium picnic experience amid the park's recreational amenities.

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Chester Town Hall

The administrative heart of Chester Township, this town hall hosts local government meetings and community events. Visitors can observe small-town governance in action during regular weekday business hours.

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West Geauga Public Library

The Geauga West Library features a Digital Legacy Lab to convert analogue media to digital formats. Browse the collection, enjoy the outdoor reading garden, or reserve a study room for focused work.

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West Geauga Plaza

West Geauga Plaza serves as Chesterland's community hub with essential retail stores and local dining options. Enjoy a relaxed shopping experience at Giant Eagle or savour authentic cuisine at My Thai Restaurant.

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Bessie Benner Metzenbaum Park

This 65-acre natural oasis features diverse habitats and a scenic creek for wildlife spotting. Explore accessible trails, then let children enjoy the nature-based playground while you relax at Wisteria Hill Shelter.

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Silo Picnic Area

Silo Picnic Area offers a peaceful 1.4-acre space in Chesterland for walking and running through lush greenery. Bring your own charcoal for grilling and pack insect repellent in summer.

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Learn more about Chesterland

Maple syrup flows freely at Patterson Fruit Farm, where families pick seasonal produce and enjoy fresh-baked treats. Explore the Western Reserve's rural charm at Holden Arboretum in nearby Kirtland, or sample local wines along the Grand River Valley wine trail.

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Top Chesterland Hotel Reviews

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent

"This is our third time as staying at the Drury in Cleveland. Each time has been consistently top notch. The building and location are excellent and in the heart of downtown. The only negative is that you can hear sounds in the hallways because of the hard surfaces and high ceilings, but this is managable."

Kimpton Schofield Hotel by IHG

10/10 Excellent

"Excellent stay! Everything was clean and within walking distance of everything you need!"

Hotel Cleveland, Autograph Collection

8/10 Good

"Hotel was very clean and staff was great. The room was nice and spacious but the bath room shower was not that great and toilet paper dispenser was so close to seat you could hardly sit down. I know it’s not a big deal but when you pay that kind of money for a room you expect better. Over all I would stay there again and would recommend it to others."

Hyatt Regency Cleveland At The Arcade

10/10 Excellent

"The Hotel was amazing with beautiful scenery and convenient stores within the building. The staff were very nice and the valets were very helpful even walking me through the process!"

Staybridge Suites Cleveland Mayfield Heights Beachwood by IHG

10/10 Excellent

"Everything was clean the bed was comfortable staff was great"

Residence Inn By Marriott Cleveland Downtown

8/10 Good

"The property was downtown but I didnt realize it was across from the baseball field. Although some traveler's like the city scene and action, it was too congested and traffic was terrible due to baseball game activity. The staff was awesome, but we didn't stay our whole visit due to changes in our plans. We would have loved to stay longer but checked out the next afternoon. The breakfast buffet was good, and all types of food and entertainment was within walking distance."

Holiday Inn Cleveland Clinic by IHG

10/10 Excellent

"The location was excellent when traveling back and forth to the hospital. Very well maintained and the staff were awesome, thank you all for providing me top-notch care during this emotional time during our lives."

Wyndham Independence

8/10 Good

"The Hotel was okay. It was clean but you can tell that it needed updating and there was some water issues going on too. The biggest issue I had was the hotel was charging my credit card every night since arrival. I went down to see why my card was being randomly charged. I never used anything as far as the phone or room service but every night there was a new charge that I had to go down a dispute. My credit card company flagged the most recent charge as fraud and block my credit card so they won't attempt to charge and I had to get a replacement card which I'm still waiting for. It was very inconvenient."

More cheap stays in Chesterland

Red Roof Inn Cleveland - Mentor/ Willoughby

4166 State Route 306 Willoughby OH

1.677.462 ₫

1.933.276 ₫ total

30 Aug - 31 Aug

includes taxes & fees

SkyLight Inn Cleveland - Willoughby

34600 Maplegrove Rd Willoughby OH

1.809.578 ₫

2.215.943 ₫ total

1 Sept - 2 Sept

includes taxes & fees

6.6/10 (1,006 reviews)

Willow Lodge Willoughby – Cleveland Mentor

35110 Maplegrove Road Willoughby OH

2.010.671 ₫

2.317.273 ₫ total

1 Sept - 2 Sept

includes taxes & fees

7.8/10 Good! (1,035 reviews)

Comfort Inn Independence - Cleveland

6191 Quarry Ln Independence OH

2.209.414 ₫

2.596.062 ₫ total

30 Aug - 31 Aug

includes taxes & fees

Comfort Inn Cleveland Downtown

1800 Euclid Ave Cleveland OH

2.641.372 ₫

3.103.612 ₫ total

30 Aug - 31 Aug

includes taxes & fees

Tru By Hilton Cleveland Midtown

6955 Euclid Avenue Cleveland OH

2.762.550 ₫

3.245.995 ₫ total

30 Aug - 31 Aug

includes taxes & fees

8.4/10 Very good! (1,637 reviews)

Hotels in Chesterland with star rating

Frequently asked questions

What's the seasonal weather like in Chesterland?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterland are January, November, December and March, with each month seeing an average of 17 cm of snowfall.

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Book Hotels in Chesterland on Expedia.com

Find hotels in Chesterland, OH from 1.933.276 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chesterland

Check prices for these dates

Filter by

Star rating

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Our top choices for Chesterland hotels

1. Drury Inn & Suites Cleveland Beachwood

2. Hyatt Place Cleveland/Lyndhurst/Legacy Village

3. Spark by Hilton Cleveland Beachwood

4. Holiday Inn Express & Suites Painesville - Concord by IHG

5. SpringHill Suites by Marriott Cleveland/Solon

6. The Aurora - a Boutique Hotel

7. Hampton Inn & Suites Cleveland-Beachwood

8. TownePlace Suites by Marriott Cleveland Solon

9. Staybridge Suites Cleveland Mayfield Heights Beachwood by IHG

10. Homewood Suites by Hilton Cleveland-Beachwood

11. Courtyard by Marriott Cleveland Beachwood

12. Cleveland Marriott East

13. Home2 Suites by Hilton Cleveland Beachwood

14. Fairfield Inn & Suites by Marriott Cleveland Streetsboro

15. Embassy Suites by Hilton Cleveland Beachwood

16. Comfort Inn Painesville - Concord

17. Hampton Inn Cleveland-Solon

18. The Glidden House

19. Holiday Inn Express Hotel & Suites Cleveland-Streetsboro by IHG

20. Best Western Plus Mentor-Cleveland Northeast

Stay near popular Chesterland attractions

Fowler's Mill Golf Course

Berkshire Hill Golf Course

Chesterland City Park

Chester Town Hall

West Geauga Public Library

West Geauga Plaza

Bessie Benner Metzenbaum Park

Silo Picnic Area

Learn more about Chesterland

Top Chesterland Hotel Reviews

Drury Plaza Hotel Cleveland Downtown

Kimpton Schofield Hotel by IHG

Hotel Cleveland, Autograph Collection

Hyatt Regency Cleveland At The Arcade

Staybridge Suites Cleveland Mayfield Heights Beachwood by IHG

Residence Inn By Marriott Cleveland Downtown

Holiday Inn Cleveland Clinic by IHG

Wyndham Independence

More cheap stays in Chesterland

Red Roof Inn Cleveland - Mentor/ Willoughby

SkyLight Inn Cleveland - Willoughby

Willow Lodge Willoughby – Cleveland Mentor

Comfort Inn Independence - Cleveland

Comfort Inn Cleveland Downtown

Tru By Hilton Cleveland Midtown

Hotels in Chesterland with star rating

Frequently asked questions

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