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 out of 5 average rating, 262 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
A loft-style bedroom features a spacious bed with light bedding, set against blue and white walls. Natural light enters through a window, and a small lamp illuminates a bedside table. A textured area rug adds comfort to the hardwood floor.
Home in Cleveland
4.98 out of 5 average rating, 570 reviews

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!*

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, 597 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
A spacious living room features a light-colored sofa paired with a textured area rug. A coffee table holds a small plant and a remote. Natural light filters through sheer curtains over a 50" Flatscreen TV, illuminating the inviting space.
Apartment in Shaker Heights
4.92 out of 5 average rating, 190 reviews

Historic District 2BR on 2nd Floor near CLE Clinic

Get comfy in this 2BR 1Bath historic district charmer in a friendly & vibrant Shaker Heights, OH neighborhood. This 2nd floor apartment offers a relaxing getaway near 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 w/ Queen Beds ✔ Relaxing Living Area ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking See more below!

Top Guest favourite
A welcoming entrance leads to a sunny sitting room featuring a blue sofa beside a wooden rocking chair. A small side table with a lamp is visible near a large window framed by soft curtains, allowing natural light to enter the space.
Guest suite in Cleveland Heights
4.96 out of 5 average rating, 502 reviews

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 or adult.

Top Guest favourite
An entertainment lounge is featured with a space-themed mural depicting an outer space view. Red accent lighting highlights the modern seating area, which includes a red couch and light-colored coffee tables. A large TV is mounted on the wall, enhancing the inviting atmosphere.
Home in Warrensville Heights
4.97 out of 5 average rating, 125 reviews

NEW! Stylish Galactic Getaway

Enjoy your stay at a newly updated Lux Airbnb! Surrounding Locations: - Cleveland Clinic | 20 mn - Pinecrest | 6 mn - Beachwood Place | 10 mn - Legacy Village | 10 mn - Hopkins Airport | 20 mn Housekeeping/Guidelines: - Before check-in, the unit will be thoroughly cleaned and inspected. - We ask you to treat our Airbnb with respect as if it was your own. - Damaged/Stolen items = Additional Fees. - The home's security code will be issued upon the reservation date. - No Smoking!

Top Guest favourite
A spacious room features exposed brick walls and a comfortable seating area with a gray sectional sofa. Light floods in from a window draped with soft curtains. A plush bed and a decorative mirror add to the inviting ambiance, while warm lighting enhances the overall atmosphere.
Apartment in Chagrin Falls
4.99 out of 5 average rating, 112 reviews

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!

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, 182 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!!

Guest favourite
A large wooden deck is positioned at the back of a two-story home, surrounded by lush green shrubs. A gas grill and outdoor seating area are visible, inviting moments of relaxation outdoors. The well-maintained yard features a vibrant green lawn and a paved driveway.
Home in Pepper Pike
4.92 out of 5 average rating, 59 reviews

Spacious 5BR Home | Near Cleveland Clinic + CWRU

🏡 About this space 🛏 5 beds • 2.5 baths • Sleeps up to 9 🎯 Two living rooms w/ smart TVs & cable 🍳 Fully stocked kitchen + outdoor gas grill 🌿 Spacious backyard w/ deck, garden & jungle gym 🏀 Basketball hoop + driveway parking 🐾 Pet-friendly! 📍 20 mins to Cleveland Clinic & Case Western Whether you're in town for work, family, or fun, this roomy, pet-friendly retreat has everything you need to relax and recharge!

Top Guest favourite
A spacious living area features a leather couch with decorative pillows and a light wood coffee table. Natural light enters through a window near the staircase, while a mounted television and decorative fireplace accentuate the cozy atmosphere.
Home in University Heights
4.9 out of 5 average rating, 105 reviews

Stylish&Bright 4BR w/Sun Deck-Close To Everything!

To book this house in 2026 & beyond, please visit https://airbnb.com/h/newheightshouse Cute & cozy, this recently updated 1930's house this full of classic charm and close to EVERYTHING! Fully furnished with brand new, modern furniture & fixtures, central A/C, 100% cotton bedding, and all of the amenities you need to make this place your home away from home.

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
4.96 out of 5 average rating, 104 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
4.95 out of 5 average rating, 151 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

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  4. Cuyahoga County
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