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

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winchester holiday rentals

2 bedrooms, iron/ironing board, WiFi, bed sheets

1. Bertha's Cabin: Rustic Ohio River Retreat

Bertha's Cabin: Rustic Ohio River Retreat
Augusta
The price is HK$784
HK$2,160 total
includes taxes & fees
8 Aug - 9 Aug
Bertha's Cabin: Rustic Ohio River Retreat
2 bedrooms, iron/ironing board, WiFi, bed sheets

2. The Cabin at 114 Main Street with Hot Tub

The Cabin at 114 Main Street with Hot Tub
Augusta
The price is HK$784
HK$2,177 total
includes taxes & fees
9 Aug - 10 Aug
The Cabin at 114 Main Street with Hot Tub
Interior

3. Del's Cabin: River Retreat Sleeps 8 w/ Hot Tub

Del's Cabin: River Retreat Sleeps 8 w/ Hot Tub
Augusta
The price is HK$2,942
HK$5,650 total
includes taxes & fees
9 Aug - 10 Aug
Del's Cabin: River Retreat Sleeps 8 w/ Hot Tub
Interior

4. Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful
Peebles
9.8 out of 10, Exceptional, (31 reviews)
"Nice quite place to stay."
United States
Gregory H.
The price is HK$824
HK$1,420 total
includes taxes & fees
10 Aug - 11 Aug
Secluded in Amish Country and peaceful
Fridge, microwave, oven

5. Country Cabin in Amish Country

Country Cabin in Amish Country
Peebles
9.8 out of 10, Exceptional, (17 reviews)
"Peaceful and Perfect. "
United States
Rodney C.
The price is HK$824
HK$1,461 total
includes taxes & fees
11 Aug - 12 Aug
Country Cabin in Amish Country
Coffee/tea maker, fridge, microwave, oven

6. Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (31 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is HK$1,059
HK$1,716 total
includes taxes & fees
10 Aug - 11 Aug
Griffis Game Hunting and/or Getaway
Interior

7. 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 are happy, repeat visitors. Great value for your vacation dollar & a great “home base” to relax in after a day’s activities."
United States
Angela M.
The price is HK$902
HK$1,506 total
includes taxes & fees
9 Aug - 10 Aug
Hunter Lodge (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)
"Clean and comfy. Great communication with host. "
United States
BeechRidgeOutfitters
The price is HK$824
HK$1,412 total
includes taxes & fees
11 Aug - 12 Aug
The Bear Den (Secluded in Amish Country and peaceful)
Interior

9. 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 HK$855
HK$1,443 total
includes taxes & fees
11 Aug - 12 Aug
Deer Lodge (Secluded in Amish Country and peaceful)
Property grounds

10. Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (28 reviews)
"Loved how cozy it was, the hot tub was very nice, I loves the cute decor and the iconic restroom movie scenes in the bathroom. Will def stay again. It was mainly nice to get away without any kiddos!"
United States
Tiffany
The price is HK$784
HK$1,396 total
includes taxes & fees
9 Aug - 10 Aug
Meadowview Guest House
Exterior

11. “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
The price is HK$840
HK$1,463 total
includes taxes & fees
25 Aug - 26 Aug
“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
Property grounds

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

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
9.4 out of 10, Exceptional, (3 reviews)
"We had a great stay, we loved the horse and goats. It was peaceful and beautiful, exactly what we needed! Will definitely stay again! "
United States
Callie J.
The price is HK$496
HK$849 total
includes taxes & fees
8 Aug - 9 Aug
Glamping Cabin | Huge Window | Cliff and Animal Views
Property grounds

13. Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.0 out of 10, Wonderful, (9 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 HK$496
HK$849 total
includes taxes & fees
8 Aug - 9 Aug
Glamping Cabin | Huge Window | Over a Creek
Property grounds

14. Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
8.6 out of 10, Excellent, (21 reviews)
"The property is very remote, secluded and quiet. It is a pet friendly property that our dog very much enjoyed. For hikers this is a great location. We were very unlucky with the weather, so no fire pit or BBQing due to torrential rain (no one can control that). Amenities are solid. It is glamping. There is a gas station approx. 10 minutes away that serves some solid breakfast…Portsmouth is about 45 minutes away for some dinner options."
United States
Stuart
The price is HK$541
HK$894 total
includes taxes & fees
11 Aug - 12 Aug
Glamping Cabin | Huge Window | Tree House Feel
TV

15. 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 HK$643
HK$1,413 total
includes taxes & fees
8 Aug - 9 Aug
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Outdoor spa tub

16. 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 HK$991
HK$1,571 total
includes taxes & fees
14 Aug - 15 Aug
Southern Ohio Retreat w/ Private Hot Tub
Interior

17. Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.6 out of 10, Exceptional, (22 reviews)
"Absolutely Wonderful. & Plan to return this Summer."
United States
Jared
The price is HK$1,059
HK$1,624 total
includes taxes & fees
13 Aug - 14 Aug
Cowboy Saloon Cabin
Interior

18. 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 HK$894
HK$1,415 total
includes taxes & fees
14 Aug - 15 Aug
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Terrace/patio

19. Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
7.2 out of 10, Good, (5 reviews)
"We enjoyed staying at this unique cabin. Our children liked the animals and enjoyed petting some of them. "
United States
Al G.
The price is HK$1,059
HK$1,216 total
includes taxes & fees
11 Aug - 12 Aug
Sleeps 4| Private Bathroom | Stunning Views
TV

20. The Outdoorsman

The Outdoorsman
Hillsboro
8.0 out of 10, Very good, (10 reviews)
"Clean and very quiet stay"
United States
Mindy
The price is HK$1,098
HK$1,335 total
includes taxes & fees
9 Aug - 10 Aug
The Outdoorsman
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
"My room overlooked the mighty Ohio River. I am from Maysville and I used to go to sleep to the sound of the trains going through. Last night one of the longest trains I've ever seen came through and because the tracks are right beside the hotel the whole building rumbled. Loved it. Really nice room, clean as can be, updated with white comforter and good mattress. When I opened the blinds at dawn, there was a huge riverboat pulled up under my window, called the American Melody. It's not a brand new hotel but nicely refurbished. Hotel staff was patient and pleasant. Breakfast was a bit limited, but good. The Keurig coffee pod choice could have been a bit better - Great Value and Dunkin Donuts brands. The hotel is walking distance for several things, including the murals on the flood wall. Don't miss lunch at the Parc Cafe down the street. Their park around the building has life-sized bronze statues of buffalo. All in all, a really nice experience."
Patricia 1-night trip
Posted 2 days ago
French Quarter Inn

Find out more about Winchester

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Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!: This holiday home rental outside of Winchester is located on a lake, and has a patio, a selection of games and a BBQ 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 that 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 wider area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.