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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

Cottage in West Union
Lucky Hooks
Fishing and relaxation. Relax with the whole family at this peaceful place to stay. This cozy brand new home is on our 70 acre farm. Enjoy watching our cattle graze and beautiful views all around our pond! Yes, we are in the country but only a 10 minute drive to town. Close to Amish country, Serpent Mound, and Buzzard’s Roost! Space: We have plenty of room for you and your family! This is a spacious three bedroom home that includes a king size bed, queen size bed, and one twin size bunk bed!
$129 per night
Cabin in Seaman
Beautiful, secluded, Amish-built cabin on 80 acres
Beautiful, secluded, Amish-built cabin on 80 acres featuring fields, woods, and privacy. Upgraded linens, kitchen with small island, cozy living room with pellet stove, private bath, and a large loft bedroom that overlooks the living room. Watch the sunset from your deck and enjoy the serenity of nature. If you are looking for peace and quiet away from the hustle and bustle...welcome home. (Pet friendly: 1-2 small/medium well behaved dog. Pet fee is $50.00. Notify owner at booking)
$165 per night
Cabin in Peebles
The Bear Den At Pine Valley Cabins
We offer 720sq ft. of space for the whole family. 1 or 2 bedrooms with extra cots, walk in closets, stand up shower, washer/dryer, fridge, microwave, full stove/oven, coffee pot, cooking pots, dish-ware, a/c / heat in each room. Eat in kitchen with Amish made dinette set. Couch folds out to make a bed. Outside smoke-less fire pit with grill option. No pets Unless approved
$92 per night

Other great vacation rentals in Winchester

Home in Peebles
Country Cabin
$102 per night
Farm stay in Seaman
The Cottage: foothills pond-side retreat
$40 per night
Rental unit in Maysville
Hippie Soul -.2 Downtown Entertainment District
$52 per night
Cabin in Seaman
Beautiful Amish-built cabin on pond
$195 per night
Private room in Winchester
Shady Grace Equine B&B
$99 per night
Guest suite in Hillsboro
Historically Charming Shipp Haus c.1891
$75 per night
Home in West Union
Tranquility Cottage
$101 per night
Cabin in Peebles
Bunk House At Pine Valley Cabins
$91 per night
Cabin in Peebles
Charming Spacious Cozy Cabin
$100 per night
Tiny home in Sardinia
Perfect Tiny Home Get Away!
$199 per night
Home in Georgetown
Maple Knoll
$120 per night
Home in Georgetown
Peaceful 3-Bedroom Log Cabin With Expansive Yard
$120 per night
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  4. Winchester