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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester vacation rentals

Exterior

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
The price is AED 1,681
AED 2,528 total
includes taxes & fees
23 Sep - 24 Sep
Quiet Farm Escape | Fishing, Nature & Views
Interior

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

Hunter Lodge (Secluded in Amish Country and peaceful)
Peebles
10.0 out of 10, Exceptional, (49 reviews)
"We had a great stay here and would definitely come back!"
United States
kathy b.
The price is AED 533
AED 830 total
includes taxes & fees
23 Sep - 24 Sep
Hunter Lodge (Secluded in Amish Country and peaceful)
Fridge, microwave, oven

3. Country Cabin in Amish Country

Country Cabin in Amish Country
Peebles
9.8 out of 10, Exceptional, (19 reviews)
"Peaceful and Perfect. "
United States
Rodney C.
The price is AED 514
AED 839 total
includes taxes & fees
23 Sep - 24 Sep
Country Cabin in Amish Country
Coffee/tea maker, fridge, microwave, oven

4. Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.6 out of 10, Exceptional, (35 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is AED 496
AED 804 total
includes taxes & fees
23 Sep - 24 Sep
Griffis Game Hunting and/or Getaway
Exterior

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 AED 444
AED 748 total
includes taxes & fees
28 Sep - 29 Sep
“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
Interior

6. 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 AED 533
AED 830 total
includes taxes & fees
23 Sep - 24 Sep
Deer Lodge (Secluded in Amish Country and peaceful)
Interior

7. 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 AED 533
AED 830 total
includes taxes & fees
23 Sep - 24 Sep
Secluded in Amish Country and peaceful
Dining

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, (46 reviews)
"Great cabin. Very clean, fully stocked kitchen, owner is very helpful."
United States
Christy A.
The price is AED 533
AED 830 total
includes taxes & fees
23 Sep - 24 Sep
The Bear Den (Secluded in Amish Country and peaceful)
1 bedroom, WiFi (free), bed sheets

9. 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 AED 367
AED 654 total
includes taxes & fees
28 Sep - 29 Sep
Meadowview Guest House
Interior

10. 1 Bed/1 Bath Guest House

1 Bed/1 Bath Guest House
Hillsboro
9.8 out of 10, Exceptional, (10 reviews)
"New and comfortable and private."
United States
Leigh K.
The price is AED 290
AED 484 total
includes taxes & fees
27 Sep - 28 Sep
1 Bed/1 Bath Guest House
Exterior detail

11. 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, (25 reviews)
"This was a great stay. The property owners were fabulous. Definitely coming back ."
United States
Atonenent R.
The price is AED 459
AED 722 total
includes taxes & fees
23 Sep - 24 Sep
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
Interior

12. Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.6 out of 10, Exceptional, (25 reviews)
"Absolutely Wonderful. & Plan to return this Summer."
United States
Jared
The price is AED 496
AED 753 total
includes taxes & fees
24 Sep - 25 Sep
Cowboy Saloon Cabin
Coffee/tea maker, fridge, microwave, oven

13. 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 AED 981
AED 1,576 total
includes taxes & fees
23 Sep - 24 Sep
Grain Bin - Unique Stay
Property grounds

14. Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.2 out of 10, Wonderful, (11 reviews)
"Had a wonderful time! Bathrooms and cabin were very clean and it was very quiet. Just what we needed."
United States
Kristen W.
The price is AED 253
AED 419 total
includes taxes & fees
23 Sep - 24 Sep
Glamping Cabin | Huge Window | Over a Creek
Property grounds

15. Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
8.6 out of 10, Excellent, (22 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 AED 253
AED 419 total
includes taxes & fees
23 Sep - 24 Sep
Glamping Cabin | Huge Window | Tree House Feel
Exterior

16. Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Valley and Cliff Views
Green Township
10.0 out of 10, Exceptional, (4 reviews)
"Very family friendly lovely views great host and respectfully so clean very nice stay"
United Kingdom
Brett W.
The price is AED 253
AED 419 total
includes taxes & fees
23 Sep - 24 Sep
Glamping Cabin | Huge Window | Valley and Cliff Views
TV

17. 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 AED 301
AED 662 total
includes taxes & fees
23 Sep - 24 Sep
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Interior

18. 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 AED 569
AED 831 total
includes taxes & fees
23 Sep - 24 Sep
Tom & Jerri's Rustic Cabin located on the lake
House (1 Bedroom) | Interior

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

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
3.0 star property
Rome
The price is AED 419
AED 663 total
includes taxes & fees
23 Sep - 24 Sep
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
1 bedroom, WiFi (free), bed sheets

20. Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!

Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
West Union
The price is AED 1,028
AED 1,229 total
includes taxes & fees
29 Sep - 30 Sep
Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
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

French Quarter Inn

French Quarter Inn

10/10 Excellent
"Wonderful staff, excellent breakfast, great room"
Thomas 1-night trip
Posted 3 hours ago
French Quarter Inn

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.