Winchester Vacation Homes

A historic downtown area with a prominent clock tower and a green-roofed building.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winchester holiday homes

A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs.

1. Quiet Farm Escape | Fishing, Nature & Views

Winchester

HK$5,746 total

includes taxes & fees

16 Nov - 17 Nov

A small, single-story cabin with a porch, a front door, and a wreath decoration.

2. “Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking

West Union

April V.

HK$1,729 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

3. Grain Bin - Unique Stay

Peebles

Jennifer J.

HK$3,686 total

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with a dark wooden table, two bar stools, a built-in oven, and pendant lighting.

4. 1 Bed/1 Bath Guest House

Hillsboro

Brenda

HK$1,397 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio area with a stone fire pit, a hot tub, and outdoor seating.

5. Sunset Cabin-Adults Only Hot Tub Getaway

Hillsboro

Kris S.

HK$2,275 total

includes taxes & fees

3 Nov - 4 Nov

A living room with a wooden entertainment center, a zebra-patterned rug, and a dining area with a table and chairs.

6. Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

Dover

Amy M.

HK$2,416 total

includes taxes & fees

12 Nov - 13 Nov

A hot tub on a wooden deck with a view of a river and trees.

7. Southern Ohio Retreat w/ Private Hot Tub

Georgetown

Austin C.

HK$3,001 total

includes taxes & fees

14 Nov - 15 Nov

A living room with a sofa, a coffee table, and a lamp.

8. Historic River Town Retreat w/ Screened Porch

Ripley

Beth B.

HK$3,652 total

includes taxes & fees

12 Nov - 13 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Paragon Inn Hillsboro

10/10 Excellent

"Clean, good value"

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

10/10 Excellent

"Jim was great to work with and easy to get a hold of. The cabin was in perfect shape and very comfortable. We've never had a cabin as well supplied as Jim's before. The pond was great for fishing. We loved catching fish one after another. The deck was great for having a fire and there was firewood provided. This is a place we plan on returning to. Highly recommended."

Find out more about Winchester