Photo by Kristin DePlatchett

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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, (671)
"Very great place to stay and all the staff was outstanding… will definitely stay there again."
United States
Debra
$78 nightly
The price is $90
Jan 5 - Jan 6, 2026
Total with taxes and fees
Holiday Inn Express & Suites Madison by IHG

Spark by Hilton Cleveland Beachwood

Spark by Hilton Cleveland Beachwood
3.0 star property
Beachwood
9.2 out of 10, Wonderful, (129)
"Clean room, great staff and service "
Canada
Phillip
$86 nightly
The price is $101
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spark by Hilton Cleveland Beachwood

Hampton Inn Madison

Hampton Inn Madison
2.5 star property
Madison
9.6 out of 10, Exceptional, (780)
"Very nice staff and clean spacious room. "
United States
Haley
$89 nightly
The price is $103
Jan 4 - Jan 5, 2026
Total with taxes and fees
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, (1013)
"Clean room, friendly staff. Plenty of restaurants around."
United States
Darius
$51 nightly
The price is $60
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Cleveland East/Mayfield Village

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby
2.0 star property
Willoughby
7.4 out of 10, Good, (1005)
"The room was nice and tidy, helped me and my family for a short stay and the price was very reasonable "
United States
Derek
$60 nightly
The price is $69
Jan 1 - Jan 2, 2026
Total with taxes and fees
Red Roof Inn Cleveland - Mentor/ Willoughby

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, (1003)
"Great stay. "
United States
Natasha
$81 nightly
The price is $93
Jan 1 - Jan 2, 2026
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Cleveland Macedonia

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast
2.5 star property
Mentor
9.2 out of 10, Wonderful, (1001)
"Clean, well-maintained hotel. Breakfast was not fantastic, but certainly more than adequate. Room was very pleasant. Staff was nice!"
United States
Katharine
$93 nightly
The price is $107
Jan 5 - Jan 6, 2026
Total with taxes and fees
Best Western Plus Mentor-Cleveland Northeast

Hampton Inn & Suites Cleveland Southeast/Streetsboro

Hampton Inn & Suites Cleveland Southeast/Streetsboro
2.5 star property
Streetsboro
9.0 out of 10, Wonderful, (1002)
"Super cleans rooms. The staff was awesome"
United States
Christopher
$114 nightly
The price is $129
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Cleveland Southeast/Streetsboro

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, (806)
"Was a great place to stay"
United States
david f
$104 nightly
The price is $120
Jan 9 - Jan 10, 2026
Total with taxes and fees
Holiday Inn Cleveland Northeast - Mentor by IHG

The Aurora Inn

The Aurora Inn
3.0 star property
Aurora
9.0 out of 10, Wonderful, (579)
"Wonderful place"
United States
Jose
$103 nightly
The price is $117
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Aurora Inn

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, (884)
"great breakfast, nice room!"
United States
LYNN
$99 nightly
The price is $117
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express & Suites Painesville - Concord by IHG

Comfort Inn Painesville - Concord

Comfort Inn Painesville - Concord
2.5 star property
Painesville
8.4 out of 10, Very Good, (1001)
"Wonderful staff good place to stay"
United States
Parker
$97 nightly
The price is $114
Jan 4 - Jan 5, 2026
Total with taxes and fees
Comfort Inn Painesville - Concord

SpringHill Suites by Marriott Cleveland/Solon

SpringHill Suites by Marriott Cleveland/Solon
3.0 star property
Solon
9.0 out of 10, Wonderful, (1002)
"Super clean, staff so friendly and breakfast was so good!!"
United States
Gina
$110 nightly
The price is $129
Jan 18 - Jan 19, 2026
Total with taxes and fees
SpringHill Suites by Marriott Cleveland/Solon

Fairfield Inn & Suites by Marriott Cleveland Streetsboro

Fairfield Inn & Suites by Marriott Cleveland Streetsboro
2.5 star property
Streetsboro
8.8 out of 10, Excellent, (719)
"Check in was a breeze and the Receptionist was very welcoming!!"
United States
VICTOR
$114 nightly
The price is $128
Dec 30 - Dec 31
Total with taxes and fees
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, (1004)
"The room was very clean housekeeping was phenomenal. And the staff were very nice and polite?. "
United States
Yvonne
$44 nightly
The price is $50
Dec 31 - Jan 1, 2026
Total with taxes and fees
Motel 6 Streetsboro, OH

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, (1504)
"The stay was wonderful, very clean and staff was great as well, would definitely staynagain."
United States
Joseph
$82 nightly
The price is $96
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hotel Indigo Cleveland Downtown by IHG

Wyndham Independence

Wyndham Independence
4.0 star property
Independence
6.4 out of 10, (1014)
"Staff was friendly rooms were clean "
United States
Charles
$52 nightly
The price is $61
Dec 30 - Dec 31
Total with taxes and fees
Wyndham Independence

Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence
2.5 star property
Independence
8.8 out of 10, Excellent, (1002)
"Love Hampton hotels"
United States
Dayanara
$89 nightly
The price is $105
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Cleveland/Independence

The Westin Cleveland Downtown

The Westin Cleveland Downtown
4.0 star property
Downtown Cleveland
8.6 out of 10, Excellent, (1945)
"Rooms were great, the people were lovely! And even though there was a huge line for check in, the staff were friendly and efficient! "
Canada
Samantha
$109 nightly
The price is $128
Dec 30 - Dec 31
Total with taxes and fees
The Westin Cleveland Downtown

Holiday Inn Cleveland-Mayfield by IHG

Holiday Inn Cleveland-Mayfield by IHG
3.0 star property
Mayfield
8.8 out of 10, Excellent, (795)
"Clean room, pleasant staff, beautiful restaurant."
United States
Carol
$82 nightly
The price is $96
Jan 25 - Jan 26, 2026
Total with taxes and fees
Holiday Inn Cleveland-Mayfield by IHG
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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

Hotels in Chesterland with star-rating

Find out more about Chesterland

Top reasons to visit Chesterland

  • Outdoor Adventures: Chesterland is a paradise for outdoor enthusiasts, offering activities like hiking, skiing, and exploring scenic parks and lakes.
  • Family-Friendly Parks: Families can enjoy quality time at local parks, featuring playgrounds and recreational facilities.
  • Charming Neighborhoods: Explore friendly neighborhoods filled with local shops and dining options for a taste of community life.
  • Wineries Nearby: Discover nearby wineries for a delightful tasting experience amidst beautiful landscapes.
  • Diverse Accommodations: Chesterland offers a range of lodging options, from cozy motels to upscale hotels, catering to various preferences.

Find great hotels near Chesterland

Discover a range of hotel accommodations in Chesterland, Ohio, tailored to meet every traveler's needs. Whether you're seeking a pet-friendly stay, a welcoming environment for LGBTQIA guests, or business-focused amenities, Chesterland has options for you. From cozy motels to top-tier hotels, you’ll find the perfect place to unwind after exploring this charming community.

  • Beachwood Extended Suites: Ideal for business travelers seeking a comfortable yet functional stay, Beachwood Extended Suites is a mere 9 miles from Chesterland. This hotel provides a business-themed environment with dedicated amenities such as ConferenceSpace, ensuring that you can conduct work efficiently while away from home. Additionally, the pet-friendly policy allows for furry companions, making it a convenient choice for those traveling with pets. With restrictions in place, the hotel ensures a welcoming environment for all guests while accommodating service animals without fees.
  • Red Roof Inn Cleveland - Mentor/Willoughby: Located 8 miles from Chesterland, the Red Roof Inn Cleveland - Mentor/Willoughby offers a welcoming atmosphere for LGBTQIA travelers and their pets. This hotel is recognized for its inclusive environment, making it a popular choice among diverse travelers. With specific pet policies, including permissions for dogs and cats, this accommodation prioritizes comfort for all guests. The property also waives fees for service animals, ensuring a stress-free stay for those in need of assistance.
  • Comfort Inn Mayfield Heights Cleveland East: Just 6 miles from Chesterland, the Comfort Inn Mayfield Heights Cleveland East seamlessly combines business amenities with a pet-friendly and LGBTQIA-welcoming atmosphere. Equipped with ConferenceSpace, a Business Center, and Meeting Rooms, it is perfect for professionals on the go. The hotel also embraces a pet-friendly policy, allowing guests to bring their beloved animals along. With the assurance of service animal fee waivers, it caters to a diverse clientele while providing a comfortable and accommodating environment.

Where to stay near Chesterland

Chesterland, Ohio, offers a delightful blend of outdoor adventure and serene tranquility. Stroll through picturesque parks and enjoy scenic walking trails, perfect for families and couples alike. Nearby, explore charming neighborhoods filled with friendly locals and budget-friendly options. For a truly peaceful getaway, visit nearby recreational areas where you can relax and unwind amidst nature's beauty. Discover the warmth of Chesterland and its surroundings for an unforgettable vacation experience.

  • Novelty: Located a mere 3 miles from Chesterland, Novelty is a charming city that draws visitors year-round with its appeal for outdoor enthusiasts and adventure seekers. The peak visiting season from June to August invites travelers to explore its picturesque landscapes and recreational areas. Whether you're looking to enjoy a day at the amusement park or indulge in some retail therapy at the local shopping center, Novelty has something for everyone. Don't miss the nearby national state park, serene lakes, and stunning valleys, which provide a perfect backdrop for your outdoor adventures.
  • Gates Mills: Also located 3 miles from Chesterland, Gates Mills is a delightful city that offers a scenic retreat for nature lovers and adventurers alike. With visitor numbers peaking from March to May, it's an ideal time to experience the lush surroundings and outdoor activities. The city features various recreational areas and shopping locations, including shopping malls, ensuring that you have a diverse range of experiences. With attractions like the national state park, tranquil lakes, and beautiful valleys nearby, Gates Mills is a great spot to immerse yourself in nature and enjoy the great outdoors.
  • Hunting Valley: Situated 4 miles away from Chesterland, Hunting Valley is a serene city that attracts visitors with its stunning scenery and outdoor adventures. The city sees moderate seasonal travel, peaking in March, July, and October, making it a fantastic destination for year-round exploration. Visitors can enjoy recreational areas, educational opportunities, and various shopping centers. The proximity to national state parks, lakes, and valleys means you'll have endless options for outdoor activities and sightseeing, making Hunting Valley a perfect addition to your Ohio itinerary.

Things to do in and around Chesterland

Chesterland, Ohio, is perfect for outdoor and adventure enthusiasts, offering a range of activities such as skiing and exploring scenic recreational areas. Families can enjoy outings at local parks, while shopping options abound in the area. Additionally, visitors can discover nearby wineries and partake in various outdoor experiences that highlight the region's natural beauty. Chesterland promises a delightful blend of adventure and relaxation for every type of traveler.

Shopping

In Chesterland, you can explore various shopping options like Legacy Village and ETON Chagrin Blvd Shopping Center, both 8 miles away, and Pinecrest Plaza Shopping, located 9 miles away. If you're up for a drive, these centers offer great entertainment and family-friendly vibes for a fun shopping experience.

Recreation

At Fowler's Mill Golf Course, enjoy a round of golf amidst beautiful landscapes and outdoor vibes. South Chagrin Reservation, just 9 miles away, offers serene trails for relaxation and wellness. StoneWater Golf Club, 7 miles from Chesterland, provides a fantastic golfing experience in a picturesque setting.

Adventure

Alpine Valley, located 4 miles from Chesterland, offers thrilling skiing experiences with a vibrant sports atmosphere. For water fun, head to Pioneer Waterland & Dry Fun Park, 13 miles away, where families can enjoy exciting rides and entertainment. Brandywine Ski Resort, 20 miles away, provides exhilarating outdoor skiing adventures.

Nightlife

For a fun night out, visit Freeway Lanes or WhirlyBall / Laser Sport, both 11 miles from Chesterland, filled with exciting arcade adventures. If you're in the mood for a movie, check out Regal Willoughby Commons, just 9 miles away, perfect for entertainment and romance.

*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, consider visiting from December to February when prices are lower, and aim for a stay on Mondays to avoid Saturday's peak rates. Use Expedia's search tool to find the best hotel deals by sorting for the lowest prices and check for Eco-certified options. Combine your hotel, flight, and activities into a package deal for extra savings. Joining Expedia’s One Key program can provide exclusive discounts and help you earn OneKeyCash for future bookings. Look for free activities in the area to enhance your experience without breaking the bank.

  • 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: Expedia's search tool enables you to customize your travel experience by selecting your budget, desired location, and additional preferences. You can easily sort the results to display the lowest prices first, ensuring you find the most affordable hotel options right away. Additionally, you can refine your search by hotel type; for instance, if you check the Eco-certified filter, you'll be shown sustainable and environmentally friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your Chesterland hotel reservations with flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Chesterland

Chesterland, Ohio, is perfect for outdoor enthusiasts and those seeking scenic adventures. Visitors can explore beautiful reserves, serene lakes, and urban parks that cater to both nature lovers and culture seekers. Nearby attractions offer even more opportunities for exploration, ensuring a fulfilling experience for all types of travelers. Whether you're looking to hike, relax by the water, or enjoy local culture, Chesterland has something for everyone.

  • Historic Kirtland: Located 7 miles from Chesterland, Historic Kirtland offers a glimpse into the past with its preserved buildings and rich cultural heritage. Explore the early 19th-century village, where you can immerse yourself in history through guided tours and informative exhibits.
  • Punderson State Park: Situated 8 miles away, Punderson State Park is perfect for adventure seekers and nature lovers alike. With its picturesque landscapes, hiking trails, and serene lake, visitors can enjoy various outdoor activities such as fishing, picnicking, and wildlife watching.
  • The Holden Arboretum: Just 7 miles from Chesterland, The Holden Arboretum is a stunning outdoor space featuring diverse plant collections and beautiful gardens. It's an ideal destination for families, offering educational programs and peaceful walking paths amidst nature's beauty.

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

Traveling to Chesterland, Ohio, is convenient with several nearby airports. Cleveland Hopkins International Airport (CLE) is 27 miles away and offers luxury accommodations like The Ritz-Carlton and Kimpton Schofield Hotel, both 10 miles from the airport. Akron-Canton Airport (CAK) is located 42 miles from Chesterland, with quality hotels such as the DoubleTree by Hilton Canton Downtown, just 9 miles away, and the nearby Embassy Suites by Hilton Akron Canton Airport, only 1 mile from CAK. For a closer option, Cuyahoga County Airport (CGF) is just 9 miles away, with excellent hotels like InterContinental Cleveland, a mere 8 miles from the airport.

Frequently asked questions

What is the best area to stay in Chesterland?
The best area to stay in Chesterland is the central village area, particularly around the intersection of Mayfield Road (US-322) and Chillicothe Road (SR-306).

This area is the heart of Chesterland, offering convenient access to local amenities and the feel of a suburban community. You'll find a selection of local shops, eateries, and services clustered along these main roads. It's a well-maintained and pleasant area for those looking for a relaxed stay.

Families will find this central location ideal due to its proximity to local parks and community facilities. It's a comfortable base for exploring the Geauga County area, with easy drives to places like The West Woods or the local library. The calm residential streets nearby make it a good choice for those traveling with children.

For travelers seeking a quiet and residential experience, the areas slightly off the main roads, but still within a short drive of the village center, offer a peaceful setting.
When is the best time to go to Chesterland?
While Chesterland is a charming place to visit year-round, the best time to go is during the late spring, summer, and early fall months, specifically from May to October.

This period offers consistently pleasant weather, ideal for enjoying outdoor activities and the natural beauty of the area. You'll find comfortable temperatures for exploring local parks, visiting farms, and attending community events. Families especially appreciate the warm weather for outdoor adventures.

The fall months, particularly September and October, are beautiful in Chesterland as the Geauga County landscape transforms with vibrant autumn foliage.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chesterland.
How can I save on a Chesterland hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Chesterland hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Chesterland hotel?
Prices for hotels in Chesterland often vary, but you can find a great deal from $51 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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