Photo by Kristin DePlatchett

Chesterland Hotels

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Our top choices for Chesterland hotels

Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG
2.5 star property
Madison
9.4 out of 10, Exceptional, (667)
"Very great place to stay and all the staff was outstanding… will definitely stay there again."
United States
Debra
The price is P4,568
P5,265 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Holiday Inn Express & Suites Madison by IHG

Hampton Inn Madison

Hampton Inn Madison
2.5 star property
Madison
9.6 out of 10, Exceptional, (779)
"Very nice staff and clean spacious room. "
United States
Haley
The price is P5,235
P6,033 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn Madison

Hilton Garden Inn Cleveland East/Mayfield Village

Hilton Garden Inn Cleveland East/Mayfield Village
3.0 star property
Mayfield
8.4 out of 10, Very Good, (1002)
"Clean room, friendly staff. Plenty of restaurants around."
United States
Darius
The price is P2,978
P3,499 total
includes taxes & fees
Dec 29 - Dec 30
Hilton Garden Inn Cleveland East/Mayfield Village

Hampton Inn Cleveland-Downtown

Hampton Inn Cleveland-Downtown
3.0 star property
Downtown Cleveland
8.8 out of 10, Excellent, (1436)
"Room was clean and staff was cool. "
United States
Anthony
The price is P4,311
P5,065 total
includes taxes & fees
Dec 26 - Dec 27
Hampton Inn Cleveland-Downtown

The Westin Cleveland Downtown

The Westin Cleveland Downtown
4.0 star property
Downtown Cleveland
8.6 out of 10, Excellent, (1905)
"Staff were amazing! Great stay in Downtown Cleveland!"
United States
Michael
The price is P6,384
P7,501 total
includes taxes & fees
Dec 22 - Dec 23
The Westin Cleveland Downtown

Holiday Inn Cleveland Northeast - Mentor by IHG

Holiday Inn Cleveland Northeast - Mentor by IHG
3.0 star property
Mentor
8.4 out of 10, Very Good, (804)
"Was a great place to stay"
United States
david f
The price is P6,107
P7,039 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Holiday Inn Cleveland Northeast - Mentor by IHG

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby
2.0 star property
Willoughby
7.4 out of 10, Good, (1002)
"The room was nice and tidy, helped me and my family for a short stay and the price was very reasonable "
United States
Derek
The price is P3,505
P4,039 total
includes taxes & fees
Dec 23 - Dec 24
Red Roof Inn Cleveland - Mentor/ Willoughby

Comfort Inn Painesville - Concord

Comfort Inn Painesville - Concord
2.5 star property
Painesville
8.4 out of 10, Very Good, (1003)
"Wonderful staff good place to stay"
United States
Parker
The price is P5,399
P6,384 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfort Inn Painesville - Concord

Motel 6 Streetsboro, OH

Motel 6 Streetsboro, OH
2.0 star property
Streetsboro
7.4 out of 10, Good, (1002)
"Clean, quiet, kind staff as well as budget friendly. Great job."
United States
John
The price is P2,167
P2,449 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Motel 6 Streetsboro, OH

Spark by Hilton Cleveland Beachwood

Spark by Hilton Cleveland Beachwood
3.0 star property
Beachwood
9.2 out of 10, Wonderful, (116)
"Great spot for a work trip."
United States
Marc
The price is P4,274
P5,022 total
includes taxes & fees
Dec 26 - Dec 27
Spark by Hilton Cleveland Beachwood

Holiday Inn Express & Suites Painesville - Concord by IHG

Holiday Inn Express & Suites Painesville - Concord by IHG
2.5 star property
Painesville
9.4 out of 10, Exceptional, (881)
"It was clean, quiet, staff was very polite. Breakfast was good too and fresh ground coffee."
United States
Virginia
The price is P5,798
P6,857 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Painesville - Concord by IHG

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG
3.5 star property
Downtown Cleveland
8.4 out of 10, Very Good, (1490)
"The stay was wonderful, very clean and staff was great as well, would definitely staynagain."
United States
Joseph
The price is P5,324
P6,256 total
includes taxes & fees
Dec 23 - Dec 24
Hotel Indigo Cleveland Downtown by IHG

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown
3.0 star property
Downtown Cleveland
7.4 out of 10, Good, (1001)
"Great friendly staff! Amazing breakfast as well."
Canada
Roberto
The price is P4,494
P5,281 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Hilton Garden Inn Cleveland Downtown

Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence
2.5 star property
Independence
8.8 out of 10, Excellent, (1001)
"We would definitely stay there again"
United States
Debra
The price is P5,235
P6,151 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn & Suites Cleveland/Independence

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

La Quinta Inn & Suites by Wyndham Cleveland Macedonia
3.0 star property
Macedonia
7.6 out of 10, Good, (1000)
"As always i enjoy staying here"
United States
Darryl
The price is P4,730
P5,451 total
includes taxes & fees
Dec 21 - Dec 22
La Quinta Inn & Suites by Wyndham Cleveland Macedonia

Holiday Inn Cleveland-Mayfield by IHG

Holiday Inn Cleveland-Mayfield by IHG
3.0 star property
Mayfield
8.8 out of 10, Excellent, (792)
"Clean room, pleasant staff, beautiful restaurant."
United States
Carol
The price is P4,568
P5,368 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Cleveland-Mayfield by IHG

Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade
4.0 star property
Downtown Cleveland
9.0 out of 10, Wonderful, (1078)
"Great Hotel"
United States
Sherian
The price is P7,966
P9,359 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hyatt Regency Cleveland At The Arcade

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast
2.5 star property
Mentor
9.2 out of 10, Wonderful, (1001)
"We stay here every time we drive to/from Co to Ny. Clean, friendly staff and comfortable. Our dog knows it well and is happy when we are there. "
United States
Paul C.
The price is P5,427
P6,254 total
includes taxes & fees
Dec 29 - Dec 30
Best Western Plus Mentor-Cleveland Northeast

SpringHill Suites by Marriott Cleveland/Solon

SpringHill Suites by Marriott Cleveland/Solon
3.0 star property
Solon
9.0 out of 10, Wonderful, (1010)
"Super clean, staff so friendly and breakfast was so good!!"
United States
Gina
The price is P6,422
P7,546 total
includes taxes & fees
Jan 9 - Jan 10, 2026
SpringHill Suites by Marriott Cleveland/Solon

Quality Inn Streetsboro - Kent

Quality Inn Streetsboro - Kent
2.5 star property
Streetsboro
7.2 out of 10, Good, (781)
"Room was nice"
United States
Derrick
The price is P3,336
P3,769 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Quality Inn Streetsboro - Kent
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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Stay near popular Chesterland attractions

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.

Pumpkin pickin'!
Photo by Kristin DePlatchett
Open Photo by Kristin DePlatchett

Top Chesterland Hotel Reviews

More cheap stays in Chesterland

Find out more about Chesterland

Top reasons to visit Chesterland

  • Outdoor Adventures: Chesterland boasts stunning lakes, parks, and nature preserves, perfect for hiking and outdoor activities.
  • Family-Friendly Attractions: The area is ideal for family outings, featuring engaging activities suitable for all ages.
  • Charming Local Shops: Explore delightful neighbourhoods filled with inviting shops and cafes within easy walking distance.
  • Wineries and Local Wines: Enjoy visits to nearby wineries, offering a taste of the region's finest wines.
  • Welcoming Accommodation: Chesterland provides a variety of pet-friendly and LGBTQIA welcoming lodging options for all visitors.

Find great hotels near Chesterland

Discover a range of delightful accommodation options in Chesterland, Ohio, perfect for both leisure and business travellers. From inviting hotels to convenient motels, you'll find properties that cater to diverse needs, including pet-friendly stays and LGBTQIA welcoming environments. Whether you're searching for the best hotels or exploring top-rated choices, Chesterland offers a warm and accommodating retreat for every visitor.

  • Beachwood Extended Suites: Ideal for business travellers and pet owners alike, Beachwood Extended Suites offers a welcoming atmosphere just 14.5km from Chesterland. This hotel combines practicality with comfort, featuring spacious rooms equipped for extended stays. Guests appreciate the pet-friendly policy, which allows pets on-site, ensuring that your furry companions can accompany you on your travels. With amenities that cater to business needs, including meeting spaces and high-speed internet access, it is a perfect choice for those on work assignments or leisure trips.
  • Red Roof Inn Cleveland - Mentor/Willoughby: Located 12.9km from Chesterland, Red Roof Inn Cleveland - Mentor/Willoughby prides itself on being a welcoming retreat for pet owners and members of the LGBTQIA community. This hotel features modern, comfortable rooms that are designed for relaxation after a day of exploration. With a pet-friendly environment and a commitment to inclusivity, guests can enjoy their stay worry-free. The property also offers convenient amenities such as free Wi-Fi and on-site parking, making it an excellent option for both leisure and business travellers.
  • Comfort Inn Mayfield Heights Cleveland East: Just 9.7km from Chesterland, Comfort Inn Mayfield Heights Cleveland East is perfect for those seeking a blend of business and leisure with a welcoming atmosphere for LGBTQIA travellers. This hotel features well-appointed rooms, ensuring a comfortable experience for all guests. The pet-friendly policy allows you to bring your pets along, making it an ideal choice for pet owners. Additional amenities include a complimentary breakfast and high-speed internet access, making it a convenient base for exploring the local area.

Where to stay near Chesterland

Chesterland, Ohio is a delightful destination for families and adventure seekers alike. With its tranquil getaways and nearby recreational areas, visitors can enjoy a relaxing yet active holiday. The surrounding neighbourhoods offer a welcoming atmosphere, perfect for exploring charming local shops and cafes within walking distance. Whether you’re seeking budget-friendly options or a romantic retreat, Chesterland presents a unique blend of friendly people and beautiful outdoor experiences waiting to be discovered.

  • Novelty: Located a mere 4.8km from Chesterland, Novelty is an inviting city that beckons outdoor enthusiasts with its stunning scenery and adventurous spirit. The peak travel season runs from June to August, making it an ideal time for visitors to enjoy its recreational areas and amusement parks. Notably, the proximity to a national state park and a picturesque lake offers ample opportunities for hiking, picnicking, and wildlife observation. With its charming local shops, Novelty provides a perfect blend of adventure and relaxation for all travellers.
  • Gates Mills: Also situated 4.8km from Chesterland, Gates Mills is a quaint city famed for its romantic atmosphere and scenic beauty. Visitors are drawn to this area particularly from March to May, when the landscape bursts into bloom. The city boasts various recreational areas and shopping centres, making it a delightful destination for couples and nature lovers alike. Explore its historic places and tranquil neighbourhoods, where you can enjoy leisurely walks by the lake, immersing yourself in the area's rich history and natural splendour.
  • Hunting Valley: Just 6.4km from Chesterland, Hunting Valley is a charming city that offers a family-friendly atmosphere and breathtaking scenery. The city sees a moderate influx of visitors, particularly in March, July, and October. Outdoor activities abound, with options such as golfing and visiting urban parks that are perfect for family outings. The nearby national state park and serene lakes provide a picturesque backdrop for exploration and relaxation, making Hunting Valley a wonderful destination for those seeking both adventure and quality family time.

Things to do in and around Chesterland

Chesterland offers an ideal destination for outdoor and family adventures, featuring recreational areas and golf courses for sports enthusiasts. Visitors can enjoy shopping options and engaging family outings while immersing themselves in the area's natural beauty. Additionally, nearby wineries provide a delightful experience for those looking to savour local wines. Whether you're seeking relaxation or adventure, Chesterland has something to offer everyone.

Shopping

In Chesterland, you’ll find West Geauga Plaza for a variety of shops close by. If you're up for a drive, visit Legacy Village or Pinecrest Plaza, both offering a vibrant mix of entertainment, dining, and shopping just 8 and 14.5km away, respectively.

Recreation

At Fowler's Mill Golf Course, immerse yourself in the serene outdoors while enjoying a round of golf amidst picturesque landscapes. Bessie Benner Metzenbaum Park offers a tranquil setting for relaxation and wellness activities, while Scenic River Retreat, just a short drive away, invites you to rejuvenate in nature's embrace.

Adventure

Pioneer Waterland & Dry Fun Park, located 20.9km from Chesterland, offers thrilling water slides and family-friendly attractions for a day of fun. Nearby, Alpine Valley, a ski field 6.4km away, provides exhilarating skiing experiences, while Brandywine Ski Resort, located 32.2km away, boasts stunning outdoor adventures on the slopes.

Nightlife

Experience the vibrant nightlife in Chesterland by visiting WhirlyBall / Laser Sport for thrilling arcade adventures or enjoy a romantic film at Regal Willoughby Commons. For more fun, head to Freeway Lanes, where the atmosphere is lively and perfect for family entertainment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chesterland

To save money on your trip to Chesterland, visit during the off-peak months of December to February when accommodation prices are lower. Opt for a Monday stay for the best rates, as Saturdays are the most expensive. Use Expedia to find eco-certified hotels and sort by price to discover the best deals. Consider bundling your hotel with flights and activities for additional savings. Additionally, explore free local attractions and utilise public transport options to keep travel costs down.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chesterland are December to February, where the prices are slightly lower. This is in comparison to August to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chesterland is Monday. The most expensive day to stay in Chesterland is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To discover the most affordable prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Chesterland hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Chesterland

Chesterland, Ohio, is an ideal destination for outdoor and family adventures, featuring attractions such as lakes, urban parks, and nature preserves. Visitors can enjoy a blend of outdoor activities, cultural experiences, and beach-like environments. Additionally, there are several nearby attractions worth exploring, making Chesterland a delightful spot for those seeking a well-rounded vacation experience.

  • Acacia Reservation: Located 12.9km from Chesterland, this scenic reserve offers tranquil walking trails and diverse wildlife. Enjoy the serene beauty of nature with opportunities for birdwatching and picnicking amidst lush greenery.
  • Euclid Creek Reservation: Situated 16.1km away, this expansive preserve features picturesque landscapes and several hiking paths. Explore the creek, discover vibrant flora, and enjoy recreational activities such as fishing and cycling.
  • Historic Kirtland: Just 11.3km from Chesterland, this historic village immerses you in rich cultural heritage. Visit restored buildings, learn about early American history, and participate in engaging community events that celebrate local traditions.

Best time to go to Chesterland

The best time to visit Chesterland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chesterland falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chesterland falls in January, visitor numbers are slightly low and weather is very cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.2°F (-3.2°C)Light RainVery CloudySlightly LowSlightly Low
February27.7°F (-2.4°C)Light RainMostly CloudySlightly LowSlightly Low
March36.3°F (2.4°C)Light RainMostly CloudyAverageAverage
April46.6°F (8.1°C)Light RainMostly CloudyAverageAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.7°F (19.3°C)Light RainMostly SunnySlightly HighAverage
July71.8°F (22.1°C)Light RainMostly SunnySlightly HighAverage
August70.5°F (21.4°C)Light RainMostly SunnySlightly HighSlightly High
September64.8°F (18.2°C)Light RainMostly SunnyAverageSlightly High
October53.4°F (11.9°C)Light RainMostly SunnyAverageSlightly High
November41.4°F (5.2°C)Light RainMostly CloudyAverageAverage
December33.4°F (0.8°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Chesterland

Flying into Chesterland, Ohio, can be conveniently done via several nearby airports. Cleveland Hopkins International Airport (CLE) is situated 43.5km away, with excellent hotel options such as the 4.5-star Kimpton Schofield Hotel and the 4-star Hyatt Regency Cleveland At The Arcade, both located 16.1km from the airport. Alternatively, Akron-Canton Airport (CAK) is 67.6km away, offering hotels like the 4-star DoubleTree by Hilton Canton Downtown, just 14.5km from the airport. For closer access, Cuyahoga County Airport (CGF) lies 14.5km from Chesterland, with nearby accommodations including the luxurious InterContinental Cleveland, positioned 12.9km away.

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 traveler data. Two other choices for your visit to the area are Wyndham Independence and Hyatt Regency Cleveland At The Arcade. 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 room reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period 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 1543 hotels and other accommodations in the surrounding area. Find out more about Chesterland.
What is there to see in Chesterland?
Favorite places to visit include Fowler's Mill Golf Course, Alpine Valley, and Chagrin River. A couple of additional sights to add to your agenda are West Geauga Plaza and Chesterland City Park. Check out what more 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 temp of 68°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterland are January, November, December, and March, with each month seeing an average of 7 inches of snowfall.

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