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

Winchester Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$644 nightly
The price is $662
Sep 30 - Oct 1
Total with taxes and fees
Quiet Farm Escape | Fishing, Nature & Views
A cozy kitchen with wooden cabinets, a stove, and a refrigerator. There is a dining table with chairs and a window with blinds.

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.
$220 nightly
The price is $220
Sep 30 - Oct 1
Total with taxes and fees
Hunter Lodge (Secluded in Amish Country and peaceful)
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.

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.
$215 nightly
The price is $223
Sep 30 - Oct 1
Total with taxes and fees
Country Cabin in Amish Country
A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an 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.
$205 nightly
The price is $215
Sep 30 - Oct 1
Total with taxes and fees
Griffis Game Hunting and/or Getaway
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.
$191 nightly
The price is $202
Oct 13 - Oct 14
Total with taxes and fees
“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
A wooden interior with a bar area featuring two stools and a countertop.

6. 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
$175 nightly
The price is $175
Oct 4 - Oct 5
Total with taxes and fees
Meadowview Guest House
A compact wooden cabin interior with a dining area, bar stool, and a small kitchen area.

7. 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
$182 nightly
The price is $189
Sep 30 - Oct 1
Total with taxes and fees
Cowboy Saloon Cabin
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.

8. 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.
$220 nightly
The price is $220
Sep 30 - Oct 1
Total with taxes and fees
Deer Lodge (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.
$220 nightly
The price is $220
Sep 30 - Oct 1
Total with taxes and fees
Secluded in Amish Country and peaceful
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

10. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (25 reviews)
"Very nice stay. "
United States
Jennifer J.
$391 nightly
The price is $402
Sep 30 - Oct 1
Total with taxes and fees
Grain Bin - Unique Stay
A wooden interior with a round dining table, chairs, a welcome sign, and a window with a view.

11. 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.
$220 nightly
The price is $220
Sep 30 - Oct 1
Total with taxes and fees
The Bear Den (Secluded in Amish Country and peaceful)
A wooden cabin entrance with a door, a lantern, a sign reading 'CABIN', and a welcome mat.

12. 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.
$173 nightly
The price is $179
Sep 30 - Oct 1
Total with taxes and fees
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.

13. 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.
$223 nightly
The price is $231
Sep 30 - Oct 1
Total with taxes and fees
Tom & Jerri's Rustic Cabin located on the lake
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

14. 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.
$114 nightly
The price is $114
Sep 30 - Oct 1
Total with taxes and fees
Glamping Cabin | Huge Window | Cliff and Animal Views
A dark green wooden building with a black door, a window, and a small balcony with a 'hello' mat.

15. 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.
$275 nightly
The price is $275
Oct 5 - Oct 6
Total with taxes and fees
Sunset Cabin-Adults Only Hot Tub Getaway
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

16. 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
$114 nightly
The price is $114
Sep 30 - Oct 1
Total with taxes and fees
Glamping Cabin | Huge Window | Tree House Feel
A wooden cabin interior with a four-poster bed, a fireplace, a dining table, and a sofa.

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

Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
West Union
$316 nightly
The price is $346
Sep 30 - Oct 1
Total with taxes and fees
Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

18. 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.
$114 nightly
The price is $114
Sep 30 - Oct 1
Total with taxes and fees
Glamping Cabin | Huge Window | Over a Creek
A modern kitchen with a dark wooden table, two bar stools, a built-in oven, and pendant lighting.

19. 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.
$145 nightly
The price is $155
Oct 11 - Oct 12
Total with taxes and fees
1 Bed/1 Bath Guest House
A wooden cabin interior with a sofa, a television, and a sliding barn door.

20. 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
Oct 4 - Oct 5
Total with taxes and fees
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
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

Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY

10/10 Excellent
"Room was clean and the bed was ok. Water was nice and hot. The rooms have been updated since the last time I visited. Staff always friendly. The lady at night was awesome."
Jennifer A 1-night trip
Posted 14 hours ago
Super 8 by Wyndham Maysville KY

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.

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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.