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.

Guest favorite

Townhouse in Augusta

4.99 out of 5 average rating, 205 reviews

☼ South Bank Station on the River w/Serene Views ☼

This Sweet Ohio River Cottage circa 1864, offers the charm & magic of bygone days, magnificent river views & blessed privacy. Enjoy a relaxing refuge from all of life's stresses in your upstairs Riverside Drive hideaway. Spectacular river views from the fire pit & picnic table as well as inside. Easy access to Main Street shops & restaurants & reliable fiber optic internet provided. The beauty & enchantment of Augusta & your graciously Southern Surroundings will refresh & elevate your spirits!

Jun 12 – 19

$91 per night
Guest favorite

Cabin in Blue Creek

4.94 out of 5 average rating, 127 reviews

The Nut House at Trails End, unique forest retreat

The Nut House is nestled in the 65000 + acre Shawnee State Forest. It is a unique COMPLETE get away in the forest in Southern Ohio. With 16’ cathedral ceilings, custom crafted artisan interior that compliments the view! Blue Creek has earned the name “The Little Smokies” for good reason. Free WIFI, Outdoor grill area, fire pit, music, fireplace, Roku TV and games are provided. Close to historic West Union and the Ohio River town of Portsmouth Miles of hiking and biking to explore!

Mar 2 – 9

$142 per night
Guest favorite

Cottage in West Union

4.96 out of 5 average rating, 56 reviews

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!

Apr 25 – May 2

$111 per night

Popular amenities for Winchester vacation rentals

Other great vacation rentals in Winchester

Guest favorite

Cabin in Hillsboro

5.0 out of 5 average rating, 15 reviews

Country Cabin

Dec 3 – 10

$90 per night
Guest favorite

Cabin in Peebles

4.97 out of 5 average rating, 29 reviews

Country Cabin (Pine Valley Cabins)

Dec 17 – 24

$126 per night
Guest favorite

Cabin in Peebles

5.0 out of 5 average rating, 41 reviews

Indian Crossing Cabin

Aug 5 – 12

$190 per night
Guest favorite

Apartment in Mount Orab

5.0 out of 5 average rating, 7 reviews

Studio 200

Jun 23 – 30

$98 per night
Guest favorite

Cabin in West Union

5.0 out of 5 average rating, 11 reviews

"Clover" 1830s Cabin on Hills Fork Farm

Jun 11 – 18

$130 per night
Guest favorite

Cabin in Peebles

4.98 out of 5 average rating, 82 reviews

Solstice Haven A-Frame on Private 20 Acres

Aug 5 – 12

$159 per night
Guest favorite

Farm stay in Hillsboro

4.99 out of 5 average rating, 67 reviews

Franklin House - quiet country getaway

Aug 6 – 13

$135 per night
Guest favorite

Cabin in Seaman

4.98 out of 5 average rating, 56 reviews

Special Promo! Beautiful Amish-built cabin on pond

Jun 11 – 18

$173 per night
Guest favorite

Cabin in Hillsboro

4.89 out of 5 average rating, 56 reviews

In the pines cabin

Jul 5 – 12

$91 per night
Guest favorite

Cabin in Peebles

4.91 out of 5 average rating, 79 reviews

Amish-Built on 6 Private Acres! Stocked Pond!

Jan 22 – 29

$112 per night
Guest favorite

Home in Sardinia

4.88 out of 5 average rating, 16 reviews

Small Town Getaway

Jul 23 – 30

$139 per night
Guest favorite

Place to stay in Ripley

5.0 out of 5 average rating, 49 reviews

Jail Break Inn in Downtown Ripley

May 6 – 13

$110 per night

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