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Vacation rentals in Chesterland

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Top-rated vacation rentals in Chesterland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage in Novelty
Country Cottage/Chagrin Village 4 miles/Sleeps 6
Guest cottage tucked away on a working honey farm just 10 minutes from Chagrin Falls, South Russell, Moreland Hills, Mayfield Heights, Gates Mills and Hunting Valley. Ideal for romantic or family getaway, enjoy the rustic country meadow view, private patio with grill and seating, campfire ring, and 3/4 acre pond.Sleeps up to 8 with a variety of sleeping accommodations-incl a King in the master, a Queen in the sleeping alcove, and 2 Twins in the sleeping loft which opens to the great room below.
$132 per night
Private room in Chagrin Falls
Large Private Suite in the Chagrin Falls Area
Private 600 sq.ft. suite in quiet community. Suite includes 1 bedroom with queen bed & dresser & closet; large living room with TV & Cable & Amazon Firestick & WiFi plus a treadmill; small library that also functions as a small kitchenette (mini-refrig, microwave, toaster, coffee maker); and a full bathroom (double vanity, shower and toilet). Recently added a Kohler Whole House Generator in case storms cause a loss of electricity. Your own private entry through owner's garage.
$80 per night
Rental unit in Chagrin Falls
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.
$80 per night

Stay near Chesterland's top sights

Photo of Oak & Embers Tavern
Oak & Embers Tavern3 locals recommend
Photo of Guido's Pizza Haven, Restaurant, and Preferred Catering Service
Guido's Pizza Haven, Restaurant, and Preferred Catering Service4 locals recommend
Photo of Red, Wine & Brew - Chesterland
Red, Wine & Brew - Chesterland3 locals recommend

Other great vacation rentals in Chesterland

Home in Chardon
Century Home with Lake Views
$154 per night
Guesthouse in Chardon
Private, Quiet 1 BR 1 Bath Chardon Guesthouse
$120 per night
Private room in South Euclid
Brick Bungalow/Upstairs Bedroom
$41 per night
Cottage in Willowick
Lake House
$120 per night
Private room in Chardon
Carmen’s Cozy Cottage 2 (Blue room)
$45 per night
Home in Chagrin Falls
Cozy Country Retreat
$105 per night
Home in Chagrin Falls
Cottage in the Village * Walk to shops/restaurants
$185 per night
Guesthouse in Willoughby Hills
Strawberry Cottage Too
$125 per night
Home in Chagrin Falls
Bliss on Bell
$200 per night
Private room in Kirtland
House in the woods
$70 per night
Home in Chagrin Falls
3 BR century home in the heart of Chagrin Falls
$206 per night
Cabin in Chardon
"Just Breathe"
$155 per night
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