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, (705 reviews)
"Very well maintained with a great breakfast and helpful staff."
United States
Jacquelyn
The price is P5,891
P6,789 total
includes taxes & fees
Apr 30 - May 1
Holiday Inn Express & Suites Madison by IHG

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast
2.5 star property
Mentor
9.2 out of 10, Wonderful, (1,002 reviews)
"Breakfast was great. Parking was convenient."
United States
Shearwood McClelland
The price is P6,627
P7,638 total
includes taxes & fees
Apr 30 - May 1
Best Western Plus Mentor-Cleveland Northeast

Comfort Inn Painesville - Concord

Comfort Inn Painesville - Concord
2.5 star property
Painesville
8.4 out of 10, Very Good, (1,001 reviews)
"Excellent customer service, great room, nice location!"
United States
Larry
The price is P6,143
P7,080 total
includes taxes & fees
May 17 - May 18
Comfort Inn Painesville - Concord

Hampton Inn Madison

Hampton Inn Madison
2.5 star property
Madison
9.6 out of 10, Exceptional, (809 reviews)
"The hotel was spotless, friendly staff, nice breakfast bar, and nice bar. "
United States
Marilyn
The price is P6,624
P7,634 total
includes taxes & fees
May 10 - May 11
Hampton Inn Madison

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Fairfield Inn & Suites by Marriott Cleveland Streetsboro
3.0 star property
Streetsboro
8.8 out of 10, Excellent, (759 reviews)
"Yummy breakfast "
United States
Julie
The price is P7,429
P8,395 total
includes taxes & fees
May 3 - May 4
Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Motel 6 Streetsboro, OH

Motel 6 Streetsboro, OH
2.0 star property
Streetsboro
7.4 out of 10, Good, (1,002 reviews)
"Good overall motel"
United States
Scott
The price is P3,097
P3,500 total
includes taxes & fees
Apr 27 - Apr 28
Motel 6 Streetsboro, OH

Super 8 by Wyndham Twinsburg/Cleveland Area

Super 8 by Wyndham Twinsburg/Cleveland Area
2.0 star property
Twinsburg
7.0 out of 10, Good, (912 reviews)
"Great deal for the price! Very clean."
United States
Justin
The price is P3,356
P3,867 total
includes taxes & fees
May 3 - May 4
Super 8 by Wyndham Twinsburg/Cleveland Area

Willow Lodge Willoughby – Cleveland Mentor

Willow Lodge Willoughby – Cleveland Mentor
2.0 star property
Willoughby
7.2 out of 10, Good, (1,002 reviews)
"Was just overall a good stay. Nice and quiet! "
United States
Demetrius
The price is P4,129
P4,759 total
includes taxes & fees
May 4 - May 5
Willow Lodge Willoughby – Cleveland Mentor

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby
2.0 star property
Willoughby
7.4 out of 10, Good, (1,006 reviews)
"Wasn't the best looking Motel. The room was a little run down."
United States
Russell
The price is P3,794
P4,373 total
includes taxes & fees
May 4 - May 5
Red Roof Inn Cleveland - Mentor/ Willoughby

Hampton Inn & Suites Cleveland Southeast/Streetsboro

Hampton Inn & Suites Cleveland Southeast/Streetsboro
2.5 star property
Streetsboro
9.0 out of 10, Wonderful, (1,001 reviews)
"Had a great stay. The remodeling was nicely done, breakfast options were excellent, and rooms clean and comfortable. "
United States
Shawn
The price is P7,420
P8,385 total
includes taxes & fees
May 3 - May 4
Hampton Inn & Suites Cleveland Southeast/Streetsboro

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, (924 reviews)
"We had a great stay. The desk clerk when we checked in was very friendly and welcoming!"
United States
Joshua
The price is P7,956
P9,169 total
includes taxes & fees
May 3 - May 4
Holiday Inn Express & Suites Painesville - Concord by IHG

Country Inn & Suites by Radisson, Macedonia, OH

Country Inn & Suites by Radisson, Macedonia, OH
3.0 star property
Macedonia
7.4 out of 10, Good, (1,000 reviews)
"Staff was amazing, breakfast was great, a little dated but room was quiet and comfortable and we would stay again for sure!!"
United States
Lucy
The price is P4,594
P5,295 total
includes taxes & fees
May 17 - May 18
Country Inn & Suites by Radisson, Macedonia, OH

Hilton Garden Inn Cleveland/Twinsburg

Hilton Garden Inn Cleveland/Twinsburg
3.0 star property
Twinsburg
8.8 out of 10, Excellent, (768 reviews)
"good stay "
United States
Ellen
The price is P6,917
P7,972 total
includes taxes & fees
May 17 - May 18
Hilton Garden Inn Cleveland/Twinsburg

The Aurora Inn

The Aurora Inn
3.0 star property
Aurora
9.0 out of 10, Wonderful, (630 reviews)
"Lovely stay"
United States
Armando
The price is P6,195
P7,001 total
includes taxes & fees
May 3 - May 4
The Aurora Inn

Spark by Hilton Cleveland Beachwood

Spark by Hilton Cleveland Beachwood
3.0 star property
Beachwood
9.2 out of 10, Wonderful, (344 reviews)
"Had a nice stay."
United States
Darrell
The price is P5,643
P6,631 total
includes taxes & fees
May 3 - May 4
Spark by Hilton Cleveland Beachwood

Super 8 by Wyndham Mentor/Cleveland Area

Super 8 by Wyndham Mentor/Cleveland Area
2.0 star property
Mentor
7.2 out of 10, Good, (1,000 reviews)
"This is definitely one of the best hotels I’ve ever been to. The staff is so friendly and welcoming that you feel like family as soon as you walk in "
United States
Brian
The price is P4,234
P4,879 total
includes taxes & fees
Apr 28 - Apr 29
Super 8 by Wyndham Mentor/Cleveland Area

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, (1,054 reviews)
"Really enjoyed the hot tub and pool"
United States
April
The price is P5,162
P5,950 total
includes taxes & fees
May 17 - May 18
La Quinta Inn & Suites by Wyndham Cleveland Macedonia

Four Points by Sheraton Cleveland-Eastlake

Four Points by Sheraton Cleveland-Eastlake
3.0 star property
Eastlake
8.4 out of 10, Very Good, (575 reviews)
"Clean, quiet, on-site restaurant and breakfast available was convenient."
United States
Mark
The price is P6,681
P7,699 total
includes taxes & fees
May 17 - May 18
Four Points by Sheraton Cleveland-Eastlake

Hampton Inn & Suites Cleveland Mentor

Hampton Inn & Suites Cleveland Mentor
2.5 star property
Mentor
8.6 out of 10, Excellent, (778 reviews)
"Super clean and the breakfast was very good "
United States
Todd
The price is P7,420
P8,552 total
includes taxes & fees
May 3 - May 4
Hampton Inn & Suites Cleveland Mentor
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.

Chesterland, Ohio, USA - 2-21-22: A small bridge in the Bessie Benner Metzenbaum Park

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 Holiday Inn Cleveland Clinic by IHG 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 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 1572 hotels and other accommodations in the surrounding area. Find out more about Chesterland.
What is there to see in Chesterland?
The picturesque setting of Chagrin River and Chesterland City Park exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Chester Town Hall and West Geauga Plaza. 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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