Holiday houses in Pepper Pike

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Top-rated holiday rentals in Pepper Pike

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Top Guest favourite
The exterior of a century home features a light grey facade, complemented by a symmetrical layout. Lush green shrubs frame the entrance, which includes a charming porch with steps leading up to the front door. A tree provides additional greenery, alongside sunny blue skies.
Home in Chagrin Falls
5.0 out of 5 average rating, 293 reviews

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!

Top Guest favourite
The exterior of a modern ranch house is showcased, featuring a vibrant red façade and a metal roof. A spacious deck is visible, complete with outdoor seating and a view of the nearby creek and surrounding trees. A gravel driveway leads to the entrance.
Home in Garrettsville
4.99 out of 5 average rating, 556 reviews

“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.

Top Guest favourite
A spacious deck offers a panoramic view of Lake Erie, with sunlight reflecting on the water. Two chairs surround a simple table, inviting relaxation. The deck is bordered by vibrant greenery, and a warm glow is cast over the scene by the setting sun.
Cottage in Willowick
4.97 out of 5 average rating, 337 reviews

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.

Top Guest favourite
A cozy bedroom features a queen-size bed with a light green coverlet. Decorative floral prints adorn the walls. A bedside lamp and a wooden nightstand are positioned nearby. A sliding mirrored closet door reflects the space, adding depth to the inviting atmosphere.
Apartment in Chagrin Falls
4.97 out of 5 average rating, 646 reviews

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.

Top Guest favourite
An open studio apartment is highlighted, featuring a fully equipped kitchen with modern appliances and a decorative wooden counter. The sleeping area includes a cozy murphy bed and a workspace, all illuminated by natural light from large windows overlooking the greenery.
Guest suite in Chagrin Falls
4.94 out of 5 average rating, 81 reviews

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.

Top Guest favourite
A bright living area features a combination of seating options, including a dark leather couch and a light-colored armchair. Natural light streams through multiple windows, illuminating the rustic wooden flooring. A door leads to the outdoor space, with a wall shelf displaying various decorative items.
Home in Chagrin Falls
4.92 out of 5 average rating, 115 reviews

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!

Top Guest favourite
Home in Warrensville Heights
4.97 out of 5 average rating, 150 reviews

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

Superhost
A bright living room features a comfortable sectional sofa and an armchair, offering seating for relaxation. Light-colored curtains frame the windows, allowing natural light to fill the space. A decorative rug is positioned on the floor, complementing the fireplace beneath the wall-mounted TV.
Home in South Euclid
4.83 out of 5 average rating, 196 reviews

Home Away From Home - Beautiful Yard

Welcome to South Euclid! This the perfect single family home to escape from the hustle and bustle of the city. Enjoy quiet streets, a nice large patio where you can sip your morning coffee and a comfortable sectional to spread out with the whole family or friends to watch TV or just chat about the day. Traveling with pets? No problem! We are pet friendly and would love to host your furry friends! Don't miss out on this 3 bedroom 1 bath today!

Top Guest favourite
A living area features a dark sofa with light-colored throw pillows, accompanied by a small ottoman. A textured area rug is placed beneath a coffee table. The kitchen area with a black fridge and island counter can be seen in the background, showcasing a blend of modern and classic design.
Apartment in Chagrin Falls
4.99 out of 5 average rating, 119 reviews

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.

Guest favourite
A stone fire pit is surrounded by a circular arrangement of natural rocks, with logs integrated into the design. Bright green chairs offer seating nearby, while a gravel path leads to a log cabin nestled among tall trees in the background.
Cabin in Solon
4.87 out of 5 average rating, 206 reviews

Little Black Cabin in the woods

We have a 900 sq.ft. , log cabin in the woods. The woods of Solon, OH. A southeast suburb of Cleveland. The cabin has 2 bedrooms, each with a queen bed and lots of built in cabinets. They share full bath. As you enter the mud room, to the right is a laundry room with washer & dryer, straight ahead the great room complete with a stone fireplace lots of windows and a small functional kitchen. Welcome to your home in the woods!!

Top Guest favourite
A modern kitchen features warm wood cabinetry and sleek stainless steel appliances. A large window allows natural light to fill the space, highlighting the light-colored countertops. Green plants and decorative items add a touch of color, while a small area rug offers warmth underfoot.
Home in University Heights
4.97 out of 5 average rating, 127 reviews

Cozy Mid-Century Modern University Heights Getaway

Welcome to our meticulously re-imagined mid-century modern space, where relaxation and style harmoniously come together. This property has undergone a complete top-to-bottom renovation, ensuring that every aspect is refreshed and revitalized. With plenty of space to unwind and recharge, you can truly kick back and enjoy your stay.

Top Guest favourite
A charming brick home is seen from the front, featuring large windows accented by black shutters. A vibrant tree with red and orange leaves stands prominently in the front yard, contrasting with the green grass and the dark awning over the entrance.
Home in Cleveland Heights
4.96 out of 5 average rating, 193 reviews

Fabulous Fairmount Retreat

Enjoy a charming, sunny home located in the heart of The Heights across from an acclaimed French bakery and buzzing Parisian style bistro. Walk to shops or the Shaker Lakes. Perfect spot for visits with family, or access to local universities, the Cleveland Clinic or University Circle museums and cultural institutions.

Popular amenities for Pepper Pike holiday rentals