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

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winchester vacation rentals

A two-story house with a front porch, a garage with two doors, and a small front yard with a flower decoration.

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
The price is ￥73,528
￥110,120 total
includes taxes & fees
Oct 12 - Oct 13
Quiet Farm Escape | Fishing, Nature & Views
A cozy room with wooden walls, a ceiling fan, a window with a view of greenery, a lamp, and a chair with a deer pillow.

2. Deer Lodge (Secluded in Amish Country and peaceful)

Deer Lodge (Secluded in Amish Country and peaceful)
Peebles
9.8 out of 10, Exceptional, (14 reviews)
"Nice place"
United States
William B.
The price is ￥23,685
￥36,633 total
includes taxes & fees
Oct 13 - Oct 14
Deer Lodge (Secluded in Amish Country and peaceful)
A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an oven.

3. Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (36 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is ￥21,317
￥34,547 total
includes taxes & fees
Oct 12 - Oct 13
Griffis Game Hunting and/or Getaway
A kitchen with wooden cabinets, a white refrigerator, a stove, and a microwave. There is a dining table with chairs and a small wooden stool.

4. Country Cabin in Amish Country

Country Cabin in Amish Country
Peebles
9.8 out of 10, Exceptional, (20 reviews)
"Peaceful and Perfect. "
United States
Rodney C.
The price is ￥18,948
￥32,243 total
includes taxes & fees
Nov 1 - Nov 2
Country Cabin in Amish Country
A small, single-story cabin with a porch, a front door, and a wreath decoration.

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

“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
West Union
10.0 out of 10, Exceptional, (2 reviews)
"Clean, peaceful and relaxing!"
United States
April V.
The price is ￥20,422
￥34,716 total
includes taxes & fees
Oct 22 - Oct 23
“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
A cozy kitchen with wooden cabinets, a stove, and a refrigerator. There is a dining table with chairs and a window with blinds.

6. Hunter Lodge (Secluded in Amish Country and peaceful)

Hunter Lodge (Secluded in Amish Country and peaceful)
Peebles
10.0 out of 10, Exceptional, (50 reviews)
"We had a great stay here and would definitely come back!"
United States
kathy b.
The price is ￥23,685
￥36,633 total
includes taxes & fees
Oct 11 - Oct 12
Hunter Lodge (Secluded in Amish Country and peaceful)
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

7. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (25 reviews)
"Very nice stay. "
United States
Jennifer J.
The price is ￥42,897
￥68,654 total
includes taxes & fees
Oct 12 - Oct 13
Grain Bin - Unique Stay
A wooden interior with a round dining table, chairs, a welcome sign, and a window with a view.

8. The Bear Den (Secluded in Amish Country and peaceful)

The Bear Den (Secluded in Amish Country and peaceful)
Peebles
9.8 out of 10, Exceptional, (47 reviews)
"Great cabin. Very clean, fully stocked kitchen, owner is very helpful."
United States
Christy A.
The price is ￥23,685
￥36,633 total
includes taxes & fees
Oct 11 - Oct 12
The Bear Den (Secluded in Amish Country and peaceful)
A kitchen with wooden cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

9. Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful
Peebles
9.8 out of 10, Exceptional, (32 reviews)
"Nice quite place to stay."
United States
Gregory H.
The price is ￥23,685
￥36,633 total
includes taxes & fees
Oct 11 - Oct 12
Secluded in Amish Country and peaceful
A compact wooden cabin interior with a dining area, bar stool, and a small kitchen area.

10. Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.6 out of 10, Exceptional, (27 reviews)
"Absolutely Wonderful. & Plan to return this Summer."
United States
Jared
The price is ￥19,185
￥30,284 total
includes taxes & fees
Oct 13 - Oct 14
Cowboy Saloon Cabin
A wooden interior with a bar area featuring two stools and a countertop.

11. Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (29 reviews)
"I was out there for a wedding and this place was great for a weekend trip."
United States
L
The price is ￥15,831
￥28,179 total
includes taxes & fees
Nov 1 - Nov 2
Meadowview Guest House
A wooden cabin with a deck, a bench, and a window.

12. Cabin 9 Encore - Includes a Homemade Country Breakfast!

Cabin 9 Encore - Includes a Homemade Country Breakfast!
West Union
The price is ￥45,791
￥57,117 total
includes taxes & fees
Oct 12 - Oct 13
Cabin 9 Encore - Includes a Homemade Country Breakfast!
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

13. Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
8.6 out of 10, Excellent, (23 reviews)
"The perfect place to connect with nature and enjoy a beautiful landscape the attention was great the beautiful place the super comfortable cabin I would come back again"
Mexico
Víctor Manuel
The price is ￥10,895
￥18,001 total
includes taxes & fees
Oct 13 - Oct 14
Glamping Cabin | Huge Window | Tree House Feel
A dark green wooden building with a black door, a window, and a small balcony with a 'hello' mat.

14. Sunset Cabin-Adults Only Hot Tub Getaway

Sunset Cabin-Adults Only Hot Tub Getaway
Hillsboro
9.8 out of 10, Exceptional, (7 reviews)
"Great weekend thank you"
United States
Kris S.
The price is ￥28,422
￥46,107 total
includes taxes & fees
Oct 12 - Oct 13
Sunset Cabin-Adults Only Hot Tub Getaway
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

15. Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
9.6 out of 10, Exceptional, (4 reviews)
"Nice place, exceptionally nice and professional host and will definitely be reserving this place again real soon!"
United States
Gregory B.
The price is ￥10,923
￥18,047 total
includes taxes & fees
Oct 11 - Oct 12
Glamping Cabin | Huge Window | Cliff and Animal Views
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

16. Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.2 out of 10, Wonderful, (11 reviews)
"Beautiful location ."
United States
Shelly R.
The price is ￥10,895
￥18,001 total
includes taxes & fees
Oct 20 - Oct 21
Glamping Cabin | Huge Window | Over a Creek
A hot tub on a wooden deck with a view of a river and trees.

17. Southern Ohio Retreat w/ Private Hot Tub

Southern Ohio Retreat w/ Private Hot Tub
Georgetown
9.2 out of 10, Wonderful, (10 reviews)
"I truly enjoyed how clean and stocked the cabin was they had everything you could possibly need and some me and my family fully enjoyed the stay "
United States
Austin C.
The price is ￥40,569
￥55,254 total
includes taxes & fees
Oct 12 - Oct 13
Southern Ohio Retreat w/ Private Hot Tub
A wooden cabin interior with a sofa, a television, and a sliding barn door.

18. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Stout
10.0 out of 10, Exceptional, (8 reviews)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
United States
Kenneth
The price is ￥12,948
￥28,440 total
includes taxes & fees
Oct 13 - Oct 14
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
A wooden cabin entrance with a door, a lantern, a sign reading 'CABIN', and a welcome mat.

19. Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village

Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
Hamersville
9.6 out of 10, Exceptional, (26 reviews)
"This was a great stay. The property owners were fabulous. Definitely coming back ."
United States
Atonenent R.
The price is ￥17,764
￥28,620 total
includes taxes & fees
Oct 12 - Oct 13
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
A wooden cabin interior with a rocking chair, a door, and a window.

20. Tom & Jerri's Rustic Cabin located on the lake

Tom & Jerri's Rustic Cabin located on the lake
Hamersville
9.8 out of 10, Exceptional, (15 reviews)
"Very cute cabin on the lake! Great stay while at the ball fields! "
United States
Malia P.
The price is ￥22,027
￥37,875 total
includes taxes & fees
Oct 11 - Oct 12
Tom & Jerri's Rustic Cabin located on the lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

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

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

10/10 Excellent
"Is a nice clean and cozy place to stay. Will definitely be booking again soon."
William G. 4-night trip
Posted 14 hours ago
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals close to top attractions in Winchester, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Winchester has to offer?

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!: Visitors like this Winchester vacation home rental. It is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family.

What’s there to see and do in Winchester?

While you're exploring the area, Rocky Fork Lake and Ripley Lions Club Community Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.