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

Our top choices for Winchester vacation 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
$232 nightly
The price is $234
Aug 6 - Aug 7
Total with taxes and fees
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
$281 nightly
The price is $284
Aug 9 - Aug 10
Total with taxes and fees
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
$750 nightly
The price is $757
Aug 6 - Aug 7
Total with taxes and fees
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.
$181 nightly
The price is $181
Aug 6 - Aug 7
Total with taxes and fees
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.
$181 nightly
The price is $187
Aug 6 - Aug 7
Total with taxes and fees
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.
$209 nightly
The price is $219
Aug 6 - Aug 7
Total with taxes and fees
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.
$192 nightly
The price is $192
Aug 6 - Aug 7
Total with taxes and fees
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
$181 nightly
The price is $181
Aug 6 - Aug 7
Total with taxes and fees
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.
$185 nightly
The price is $185
Aug 6 - Aug 7
Total with taxes and fees
Deer Lodge (Secluded in Amish Country and peaceful)
1 bedroom, WiFi (free), bed sheets

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
$178 nightly
The price is $178
Aug 9 - Aug 10
Total with taxes and fees
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
$174 nightly
The price is $184
Sep 1 - Sep 2
Total with taxes and fees
“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.
$114 nightly
The price is $114
Aug 6 - Aug 7
Total with taxes and fees
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.
$114 nightly
The price is $114
Aug 6 - Aug 7
Total with taxes and fees
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
$114 nightly
The price is $114
Aug 10 - Aug 11
Total with taxes and fees
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
$176 nightly
The price is $180
Aug 6 - Aug 7
Total with taxes and fees
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.
$200 nightly
The price is $200
Aug 6 - Aug 7
Total with taxes and fees
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
$197 nightly
The price is $205
Aug 6 - Aug 7
Total with taxes and fees
Cowboy Saloon Cabin
House (1 Bedroom) | 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
$175 nightly
The price is $180
Aug 6 - Aug 7
Total with taxes and fees
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.
$155 nightly
The price is $155
Aug 6 - Aug 7
Total with taxes and fees
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
$160 nightly
The price is $170
Aug 9 - Aug 10
Total with taxes and fees
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
"Great boutique hotel in a charming and fun town. Request a room with a view of the Ohio River and the bridge!"
Douglas 2-night trip
Posted 22 hours ago
French Quarter Inn

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $114 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Modern Farmhouse, 3 bedrooms, 2 full baths, sleeps 8 : Visitors like this Winchester vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.