Holiday rentals in Pepper Pike

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!

Modern Farmhouse Chagrin Falls Beachwood CVNP

Private Custom-Renovated Modern Farmhouse tucked into a wooded setting minutes from downtown Chagrin Falls and Hunting Valley. Neighboring Beachwood, Moreland Hills & Pepper Pike. 20min to Cuyahoga Valley National Park. Heated slate floors, spa like bath with endless hot water, dual work spaces & true privacy. Affectionately dubbed “The Wayback,” this home sleeps 6 with 2 private bedrooms, a fully equipped kitchen, and upscale amenities near Pinecrest & ETON dining, shopping, and entertainment.

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 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.

Backyard Oasis in Chagrin Falls

Immerse yourself in history at this renovated Chagrin Falls oasis! This apartment was originally built for secret service members as President Jimmy Carter's son once owned this home. This beautifully renovated studio apartment tucked away amongst the trees, boasts bright natural light , has a fully equipped kitchen, a convenient workspace, and a cozy murphy bed with queen mattress. Conveniently located, it's only a few minute walk to downtown Chagrin's charming shops, cafes and restaurants.

Hot Tub Escape | Sleeps 10 | Pets + Huge Yard

🏡 Spacious 3,200 sq ft retreat for families & groups 🛏 5 King Beds • Sleeps up to 10 🛁 2.5 Baths ♨️ Private hot tub 🎯 Two living rooms w/ Smart TVs + cable 🍳 Fully stocked kitchen + gas grill 🌿 Large backyard w/ deck, jungle gym + garden 🏀 Basketball hoop + driveway parking 🐾 Pet-friendly 📍 20 mins to Cleveland Clinic & Case Western Reserve University Whether you're in town for work, family, or fun, this roomy, pet-friendly retreat has everything you need to relax and recharge!

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.

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.

Rare Cleveland Apt: Little Italy! W/Sauna&Hot tub!

Fall in love with this charming, newly updated 1-bedroom, 1-bath lower unit triplex apartment situated in the heart of Little Italy, walking distance from University Circle, UH Hospital, Cleveland Museum of Art, Botanical Garden, Public Transportation and much more. Apartment is complete with a well-equipped kitchen, Smart TV, laptop workspace, and modern furnishings, this vacation/business rental delivers all the essentials so you can spend more time relaxing and exploring.

Private Victorian suite with two rooms and a bath

You’ll love this newly remodeled third floor suite in our large century home located near Coventry Village/University Circle/Cleveland Clinic. The private suite with separate entrance and stairs has an air conditioned large bedroom with a firm queen bed, a sunny sitting room with a futon and a bathroom (shower) finished in Victorian ornate wood trim! Off street parking is in the rear. Our place is great for couples or business travelers, and the futon can sleep a child on.

Star Wars–Themed Home w/ Arcade | Family-Friendly

Enjoy your stay at a newly updated Star Wars–themed family home- perfect for relaxing getaways, extended stays, or families needing comfortable temporary housing nearby. 📍 Nearby: • Cleveland Clinic – 20 min (medical stays & visits) • Pinecrest – 6 min (dining & shopping) • Cuyahoga Valley National Park – ~20 min (trails & scenic railway) • Downtown Cleveland – ~20 min (museums & sports) • Hopkins Airport – 20 min (easy travel access) 🚭 Smoke-free & pet-free home