Vacation 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.

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.

Lake House with Amazing Views

Amazing location right on Lake Erie. This cozy lake house has a large kitchen, full bathroom and a living room/bedroom with king-size bed. The cottage is off by itself so you can enjoy your seclusion, but we live about 200 feet away so we can assist you if you need us. Enjoy a morning coffee on the deck while watching nature, spectacular sunsets on the private patio, and falling asleep to the sounds of the lake. You will be blown away by the beauty and peacefulness of this amazing cottage.

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!

“Willow Ledge at Silver Creek”with Private Hot Tub

New Construction Modern Ranch House features rustic upscale design with beautiful cozy interiors and comfort at every turn. Stunning views await with floor to ceiling windows overlooking beautiful Silver Creek and surrounding nature. Private deck is spacious and inviting with oversize hot tub, concrete fire pit, gas grill, and outdoor dining furniture. A few minutes from great restaurants, the Brewery at Garrett’s Mill, and the coolest Coffee Shop. Perfect weekend getaway or business stay.

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.

Lydia's Lake Erie Cottage

In the heart of Willoughby, a cozy cottage awaits you as the perfect getaway spot. Situated on the shores of Lake Erie, you'll be able to enjoy stunning lake views on the water's edge. Inside, you'll find a cozy and well-appointed space, complete with a fully stocked kitchen and outdoor grill, Unwind by the fireplace in the living room or catch up on your favorite shows on the smart TV. Stay connected with the free WiFi, and take advantage of the laundry with a washing machine and dryer.

Residential Apartment w/Drumkit

Quiet apartment in residential neighborhood attached to owner occupied home. Beautiful scenic large backyard with dining area & fire pit. Electronic Roland, TD-8 drum kit to be enjoyed by everyone: If you’ve ever wanted to play the drums and haven’t had a chance, or if you are a current player looking to keep your chops in shape!! Located 25 min. from Cleveland with a beautiful Great Lake (Erie) at the end of the st.&Lakefront Lodge Park 1/2 mi. Many food/grocery establishments nearby.

Lakeview Retreat

Enjoy the unobstructed lake views very close to downtown Chardon, several golf courses, the Holden Arboretum, Alpine Valley Skiing, and adjacent to Bass Lake's amenities. Inside, you'll love the cozy fireplace, 4 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. We have the highest reviews/year in the area!

Private, Quiet 1 BR 1 Bath Chardon Guesthouse

Enjoy a respite at this peaceful and centrally-located, renovated guesthouse. Large 1BR w full bath. Sleep with the windows open - it's that quiet. Living room and full, eat-in kitchen. Private patio for outdoor dining. Walk to historic Chardon Square and enjoy its many festivals & activities. Easy drive to Amish country, wineries, Lake Erie and its coastal towns and beaches, The Great Geauga County Fair, 40 minutes to downtown Cleveland.

1br-1bth- Furnished Oasis in Chardon

The apartment is above a detached garage. The spacious floor plan is modern and fresh, on-site laundry, a full kitchen, walk-in closet and large private bathroom, this apartment feels just like home. Long term lease is available for a discounted rate. The apartment is located on a busy street (“busy” for a small town) you will hear cars and motorcycles drive by. Please take this into consideration when booking.

Rocking H Lakefront Cottage

Come unwind at this lakeside cottage on Little Punderson Lake. Watch eagles and herons from your morning coffee or enjoy sunsets with wine. Guests love this peaceful spot to recharge. Next to Punderson State Park with trails, fishing, kayaking, and golf. Near Amish country with great restaurants. A true rural getaway. Please read full description before booking.