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.

Lake Erie Getaway

Enjoy the wondrous beauty and sunsets of Lake Erie, the 11th largest freshwater lake in the world. From the back yard you can swim or fish. 2 bedroom/2 bathroom house with cozy electric fireplace in family room . 1300 square feet of first floor living on Lake Erie.Lake views from nearly every room. Private fenced backyard with over 400 plants. Twenty minutes from downtown Cleveland and University Circle area, 10 minutes to downtown Willoughby and a 5 minute walk to the grocery stores and deli

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!

Mid-Century Modern Ranch in quiet neighborhood

Stay in our newly remodeled Mid-Century classic! It's updated to incorporate today's conveniences with focus on the original vision of the 1965 builder who constructed it for its long time owners. Located just off Interstate 90 in a quiet neighborhood, the home offers an open living space, a lower level recreation room for playing pool or ping pong, a large fenced in yard, and a covered back porch to enjoy morning coffee or an evening glass of wine as you watch the many neighborhood deer.

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!

New! “Modernistic Retreat”

Elevate your stay in this bright, elegant and spacious 3rd floor apartment that offers the perfect blend of tranquility and urban convenience. Less than 10 minutes from Cleveland Clinic, 8 min from Case Western University, 17 min from Rock and Roll Hall of Fame, 18 min from Cleveland Browns Stadium, 20 min from Downtown, 28 min from Cleveland Airport and 45 min from Blossom Music Venue. Moments from charmed local neighborhoods such as Coventry, Little Italy, Cedar Fairmont and Lee Rd.

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 w AC

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.

The Mill House

The Mill House, built in 1890, sits in downtown Chagrin Falls, a former mill town with a history of 9 mills powered by the Chagrin River. Settlers in the mills' early days lived in the village's old homes, inspiring the name "Mill House." Nearby, you'll find restaurants, coffee shops, stores, a grocery, pharmacy, the famous popcorn shop, waterfalls, and the historic Chagrin Falls Hardware. We only accept guests that have reviews.

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.