Chesterland Holiday Rentals, Ohio: Private House Rentals

A wooden bridge over a snow-covered path in a forest.

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Our top choices for Chesterland hotels

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

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

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

A modern restaurant with booths, high tables, and a bar area.

1. Drury Inn & Suites Cleveland Beachwood

Orange

Jesse

Rp2.185.573

Rp2.568.048 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

A conference room with a round table, four orange chairs, a chandelier, and large windows with curtains.

2. Spark by Hilton Cleveland Beachwood

Beachwood

james

Rp1.748.243

Rp2.054.186 total

includes taxes & fees

4 Oct - 5 Oct

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.

A reception desk with a wooden finish and a digital screen, accompanied by a smaller desk with a phone.

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

3. Courtyard by Marriott Cleveland Beachwood

Beachwood

Janeen

Rp2.209.432

Rp2.596.082 total

includes taxes & fees

28 Sept - 29 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.

4. Hyatt Place Cleveland/Lyndhurst/Legacy Village

Lyndhurst

Barbara

Rp2.597.820

Rp3.052.438 total

includes taxes & fees

4 Oct - 5 Oct

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

A conference room with a long table, yellow chairs, a flat-screen TV, and framed geometric art on the wall.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

A hotel room with a kitchenette, a bed, a window with blinds, and a view of the outdoors.

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

Painesville

Sandra

Rp1.899.096

Rp2.188.708 total

includes taxes & fees

25 Oct - 26 Oct

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 lobby with round tables and chairs, a reception desk, and a wooden partition.

6. SpringHill Suites by Marriott Cleveland/Solon

Solon

John

Rp1.964.489

Rp2.308.274 total

includes taxes & fees

4 Oct - 5 Oct

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.

A reception area with a wooden counter, a staircase leading to another room, and a large window with natural light.

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

7. The Aurora - a Boutique Hotel

Aurora

Steven

Rp1.572.129

Rp1.776.506 total

includes taxes & fees

4 Oct - 5 Oct

A restaurant with wooden booths and tables, featuring signs for 'Chianti' and 'Bardolino'.

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

An outdoor patio area with round tables and chairs, surrounded by greenery and umbrellas.

A gym with treadmills, elliptical machines, and dumbbells.

8. Holiday Inn Cleveland-Mayfield by IHG

Mayfield

Daniel

Rp2.060.340

Rp2.420.900 total

includes taxes & fees

25 Oct - 26 Oct

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

A spacious lobby with a fireplace, seating areas, and a high ceiling with wooden paneling.

9. Homewood Suites by Hilton Cleveland-Beachwood

Beachwood

Eric

Rp2.482.799

Rp2.917.290 total

includes taxes & fees

4 Oct - 5 Oct

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

A bar area with a bartender, a wine cooler, and a well-stocked bar with various bottles and glasses.

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

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

10. Embassy Suites by Hilton Cleveland Beachwood

Beachwood

Mike

Rp2.323.111

Rp2.729.655 total

includes taxes & fees

8 Oct - 9 Oct

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

A hotel lobby with a sofa, chairs, a small table, a reception desk, and a TV screen.

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

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

11. TownePlace Suites by Marriott Cleveland Solon

Solon

Terry

Rp1.918.804

Rp2.254.594 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

An outdoor patio with wicker furniture and string lights.

12. The Glidden House

University Circle

Seshu

Rp3.206.964

Rp3.768.183 total

includes taxes & fees

27 Sept - 28 Sept

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

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

An outdoor patio area with a pergola, seating, and flower planters.

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

13. Hampton Inn & Suites Cleveland-Beachwood

Orange

Donella

Rp1.968.610

Rp2.313.117 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A Marriott hotel with a brick facade, large windows, and a well-lit entrance.

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

14. Cleveland Marriott East

Warrensville Heights

Chi Yun

Rp2.649.776

Rp3.113.486 total

includes taxes & fees

27 Sept - 28 Sept

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.

15. Home2 Suites by Hilton Cleveland Beachwood

Beachwood

Dovari

Rp2.030.896

Rp2.386.303 total

includes taxes & fees

11 Oct - 12 Oct

A modern kitchen with a built-in island, stainless steel appliances, and dark wooden cabinets.

A modern hotel room with a dining area, kitchenette, and a living area with a sofa and ottoman.

A modern kitchen with dark cabinets, stainless steel appliances, and a white dining table with patterned chairs.

A hotel room with a kitchenette, a dining area with a table and chairs, a bed, a TV, and a desk with a chair.

16. Staybridge Suites Cleveland Mayfield Heights Beachwood by IHG

Mayfield Heights

Michael

Rp2.329.080

Rp2.736.669 total

includes taxes & fees

27 Sept - 28 Sept

A modern living room with a sofa, armchairs, a coffee table, and a kitchen area with a counter and pendant lights.

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

A compact hotel room with a kitchenette, a bed, a desk, and a chair.

A modern hotel lobby with wooden flooring, a blue accent wall, yellow seating, and a TV.

17. Comfort Inn Mayfield Heights Cleveland East

Mayfield Heights

Nathaniel

Rp2.021.641

Rp2.375.428 total

includes taxes & fees

27 Sept - 28 Sept

A modern hotel lobby with round tables, bar stools, and a seating area.

A swimming pool with lounge chairs and a sunbed, surrounded by yellow walls and a tiled floor.

A hotel reception area with a wooden reception desk, a large screen displaying a scenic image, and a vending machine.

A modern kitchen with a microwave, sink, and wooden cabinets. There is a round mirror on the wall and a window with blinds in the background.

18. Hampton Inn & Suites Oakwood Village-Cleveland

Oakwood Village

Suzanne

Rp2.323.111

Rp2.729.655 total

includes taxes & fees

8 Oct - 9 Oct

A bar area with multiple seating options, a counter with a cash register, and a neon sign for Great Lakes Brewing Co.

A modern kitchen with a built-in refrigerator, a coffee station, and a variety of food display cases.

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

A Holiday Inn hotel with a modern design, featuring a prominent entrance and a parking lot.

19. Holiday Inn Cleveland Northeast - Mentor by IHG

Mentor

Scott

Rp2.112.296

Rp2.434.421 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a bathtub, and a painting of a bridge.

A kitchen with a microwave, coffee maker, and a sign about morning charge.

A multi-story hotel with a 'Welcome' sign, parking spaces, and a landscaped area with plants.

20. Willow Lodge Willoughby – Cleveland Mentor

Willoughby

Josh

Rp1.371.808

Rp1.580.991 total

includes taxes & fees

30 Sept - 1 Oct

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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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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 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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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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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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Sunnybrook Preserve

This 73-acre natural haven showcases unique wetlands and conifer forests along 1.6 miles of scenic trails. Explore the diverse habitats, then unwind at the picnic pavilions with stone fireplaces.

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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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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.

See all hotels in Chesterland

Top Chesterland Hotel Reviews

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent

"A+"

Holiday Inn Cleveland Clinic by IHG

10/10 Excellent

"The waitstaff in the cafe was wonderful regarding my dietary needs. The food was fantastic. The convenience store and vending machine were well stocked. A fridge and microwave in the room. It was perfect!"

Embassy Suites by Hilton Cleveland Rockside

10/10 Excellent

"Walking distance to Top Golf!"

Hilton Garden Inn Cleveland Downtown

10/10 Excellent

"I liked the location. I exercise room equipment is small and the treadmill did not work."

More cheap stays in Chesterland

Econo Lodge Cleveland Southeast - Kent

9789 State Route 14 Streetsboro OH

Rp913.716

Rp1.032.499 total

15 Oct - 16 Oct

includes taxes & fees

7.8/10 Good! (1,000 reviews)

Willow Lodge Willoughby – Cleveland Mentor

35110 Maplegrove Road Willoughby OH

Rp1.371.808

Rp1.580.991 total

30 Sept - 1 Oct

includes taxes & fees

Extended Stay America Premier Suites - Cleveland - Independence

6025 Jefferson Dr Independence OH

Rp1.581.804

Rp1.858.620 total

25 Oct - 26 Oct

includes taxes & fees

Comfort Inn Cleveland Downtown

1800 Euclid Ave Cleveland OH

Rp1.812.024

Rp2.129.128 total

11 Oct - 12 Oct

includes taxes & fees

Best Western Plus Mentor-Cleveland Northeast

8434 Mentor Avenue Mentor OH

Rp1.876.164

Rp2.162.282 total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (1,007 reviews)

Tru By Hilton Cleveland Midtown

6955 Euclid Avenue Cleveland OH

Rp1.846.781

Rp2.169.968 total

4 Oct - 5 Oct

includes taxes & fees

8.4/10 Very good! (1,622 reviews)

Frequently asked questions

Where is the best place for a stay in Chesterland?

The Westin Cleveland Downtown, located 18.3 mi (29.5 km) from the heart of Chesterland, is a top choice for your stay, based on our traveller data. Other good options for your stay in the area are Extended Stay America Premier Suites - Cleveland - Independence and Hotel Indigo Cleveland Downtown by IHG. See all available top hotels, or vacation rentals in Chesterland.

If I need to cancel my hotel reservation in Chesterland, will I receive a refund?

Yes, the majority of hotel reservations are refundable if you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you have a reservation that's non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chesterland.

What is staying in Chesterland like?

Visitors can enjoy all that Chesterland has to offer, including the golf courses and ski areas. There are 1499 hotels and other accommodation options in the surrounding area. Find out more about Chesterland.

What is there to see in Chesterland?

Favourite places to visit include Alpine Valley, Chagrin River and Berkshire Hill Golf Course. A couple of additional sights to add to your itinerary are Fowler's Mill Golf Course and Chesterland City Park. Take a look at what more there is to see and do in Expedia's Chesterland guide.

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 Rp1.032.499

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chesterland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chesterland hotels

1. Drury Inn & Suites Cleveland Beachwood

2. Spark by Hilton Cleveland Beachwood

3. Courtyard by Marriott Cleveland Beachwood

4. Hyatt Place Cleveland/Lyndhurst/Legacy Village

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

6. SpringHill Suites by Marriott Cleveland/Solon

7. The Aurora - a Boutique Hotel

8. Holiday Inn Cleveland-Mayfield by IHG

9. Homewood Suites by Hilton Cleveland-Beachwood

10. Embassy Suites by Hilton Cleveland Beachwood

11. TownePlace Suites by Marriott Cleveland Solon

12. The Glidden House

13. Hampton Inn & Suites Cleveland-Beachwood

14. Cleveland Marriott East

15. Home2 Suites by Hilton Cleveland Beachwood

16. Staybridge Suites Cleveland Mayfield Heights Beachwood by IHG

17. Comfort Inn Mayfield Heights Cleveland East

18. Hampton Inn & Suites Oakwood Village-Cleveland

19. Holiday Inn Cleveland Northeast - Mentor by IHG

20. Willow Lodge Willoughby – Cleveland Mentor

Stay near popular Chesterland attractions

Fowler's Mill Golf Course

Berkshire Hill Golf Course

Chester Town Hall

West Geauga Plaza

West Geauga Public Library

Chesterland City Park

Sunnybrook Preserve

Bessie Benner Metzenbaum Park

Learn more about Chesterland

Top Chesterland Hotel Reviews

Drury Plaza Hotel Cleveland Downtown

Holiday Inn Cleveland Clinic by IHG

Embassy Suites by Hilton Cleveland Rockside

Hilton Garden Inn Cleveland Downtown

More cheap stays in Chesterland

Econo Lodge Cleveland Southeast - Kent

Willow Lodge Willoughby – Cleveland Mentor

Extended Stay America Premier Suites - Cleveland - Independence

Comfort Inn Cleveland Downtown

Best Western Plus Mentor-Cleveland Northeast

Tru By Hilton Cleveland Midtown

Frequently asked questions

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