Holiday rentals in Chesterland

Avonlea Gardens & Inn - Entire House

Avonlea Inn is a century home with unique vintage charm! 3 bedrooms (upstairs - 1 king & 1 queen, main floor - 1 queen & queen pullout sofa in living room). Dining room, kitchen, & front porch. Located on same property as our native plant nursery - you are welcome to wander! Renting half the house is possible - please see separate listings for the Rose Suite (2 bedrooms on 2nd floor) or the Bluebell Suite (1 bedroom, pullout, full kitchen on 1st floor). Pets allowed only if renting entire house.

Modern Loft ~ Near Cle Clinic ~ Long Stays OK

Relax in this newly renovated 2BR 1Bath unique and modern loft in a friendly & vibrant Shaker Heights, OH neighborhood. This upper unit loft offers a relaxing getaway near great restaurants, shops, attractions, landmarks, and major hospitals and employers, making it ideal for traveling nurses and business travelers looking for an extended stay. ✔ 2 Comfy Bedrooms ✔ Relaxing Living Area ✔ Fully Equipped Kitchenette ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Cooling ✔ Washer/Dryer ✔ Parking See more below!

Maple Syrup Sugarhouse Studio Apartment

Take it easy at this unique and tranquil getaway at Butternut Maple Farm in the heart of Burton Township right by the Geauga County Fairgrounds and just miles from Amish Country. This private brand new, fully furnished smoke-free studio apartment is on the second floor of the sugarhouse with a gorgeous attached deck perfect for your morning coffee. During maple sugar season (January-March), you receive front row seats to watch and/or participate in making our award winning organic maple syrup.

Cottage in the Village * Walk to shops/restaurants

This cute little century home (1000 sq. ft.) is located on a quiet street just steps from the shops and restaurants in the village. Park your car and walk to the falls, grab a bite to eat, and explore. Back at the house, grab a book and read on the covered front porch, or relax in the sun on the back deck. The lower level yard has a fire ring to roast marshmallows and a circular staircase leading up to a playhouse for the kids. This cozy spot is the perfect place to be to explore Chagrin Falls!

Cozy + Bright Lakeshore Cottage

Relax in this sunny cottage steps away from the Lake Erie shore. Comfy living room opens to the dining room (or home office - you choose!) Kitchen is well stocked and ready for the chef. Main bedroom and full bath are loft-style on the second level. Additional smaller bedroom and half bath on the first floor. Washer/dryer in the basement. Private driveway. Friendly and authentic Cleveland neighborhood. Terrific natural sunlight will brighten your stay and make THIS your Cleveland *happy place!*

Cozy Apartment in Charming Village

Cozy apartment with private entrance attached to historic house. Central location in this charming tourist village of Chagrin Falls, a short walk to the natural waterfalls, over 20 great restaurants, two ice cream shops & boutique shopping. Low ceilings & compact bathroom, but full kitchen and parking for one car. Non-smokers only. No pets - out of consideration for future guests. Guests must be able to climb stairs to access apartment. Air conditioning is available during the summer season.

Willow Woods Retreat | Historic Farmhouse + Pond

🌳 Historic 1830s farmhouse on 4 secluded acres 🛏 4 bedrooms • 5 beds • 2 bathrooms • Sleeps 9 ✨ Renovated w/ vintage charm + modern comfort 🛁 Master bath w/ jetted tub & skylight 🍳 Fully stocked kitchen • Dining for groups 🔥 Outdoor patio • Gas grill • Fire pit 📍 Just 5 min drive to the famous Kirtland Temple 🌊 Private pond w/nature views 🚗 Plenty of driveway parking for all your vehicles Unwind at Willow Woods Retreat — a storybook farmhouse escape perfect for families and friends!

Lakeview Retreat

Enjoy the unobstructed lake views very close to downtown Chardon, several golf courses, the Holden Arboretum, and Alpine Valley Skiing. We are a short walk to Bass Lake and its amenities. Inside, you'll love the cozy fireplace, 3 season porch, 4K TV, games, and puzzles. You can also just sit and relax while enjoying the view with a glass of wine in the enclosed porch. There is even a writing desk with views of the lake. Well-mannered dogs are welcome as long as they stay off the furniture.

Chardon Loft

Large private 2nd floor studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels. The furnace is nontraditional. It is not located in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Bell Street by the Falls

This 1100 sq ft gem is located just 3 blocks from the center of town and the historic Chagrin Falls viewing area. The original structure features exposed hand cut beams from the 1800's and its charm continues down to the rustic flooring. After appreciating the historic elements, you'll enjoy the remaining areas that have been completely updated and ready for your enjoyment and relaxation. Sip your coffee from the front porch or walk to shopping and dining. You cannot beat the location!

On The Falls #2

Best location in Chagrin Falls! Spectacular sweeping views of the famous Chagrin Falls out of every window. It's hard not to stare out the window for hours as you become immersed with the view and the sounds of falling water. This aparment is above the Starbucks in town and is a staircase away from everything downtown Chagrin Falls has to offer. Come dine at the amazing restaurants, shop all the styles at eclectic shops and soak up the views!

Davis Ranch 5 Bedrooms Sleeps 10 & 3 1/2 baths

Overlooking Davis Lake, beautiful sunrises & 8 Acres. Will rent to 2 - 10 people on any given night. Guests will have the entire home as Host does not book more than one guest. No 1 Night stays please. Children under 2 there is no charge. Dogs no charge. I believe in making your stay a very memorable occasion. Please read the reviews that really tell the Ranch Story. In this Century Home you will have Three Full Baths and One 1/2 bath.