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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester vacation rentals

A spacious living area with a large wooden dining table, a modern pendant light, and a view of the adjacent kitchen.

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
$675 nightly
The price is $693
Oct 22 - Oct 23
Total with taxes and fees
Quiet Farm Escape | Fishing, Nature & Views
A kitchen with wooden cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

2. 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.
$232 nightly
The price is $232
Oct 22 - Oct 23
Total with taxes and fees
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, (20 reviews)
"Peaceful and Perfect. "
United States
Rodney C.
$198 nightly
The price is $205
Nov 1 - Nov 2
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
9.8 out of 10, Exceptional, (36 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
$209 nightly
The price is $219
Oct 26 - Oct 27
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.
$209 nightly
The price is $220
Nov 8 - Nov 9
Total with taxes and fees
“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
A compact wooden cabin interior with a dining area, bar stool, and a small kitchen area.

6. 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
$185 nightly
The price is $192
Oct 26 - Oct 27
Total with taxes and fees
Cowboy Saloon Cabin
A modern kitchen with a dark wooden table, two bar stools, a built-in oven, and pendant lighting.

7. 1 Bed/1 Bath Guest House

1 Bed/1 Bath Guest House
Hillsboro
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and neat! Very comfortable place to stay. We enjoyed out visit and would definitely book this property again."
United States
Brenda
$166 nightly
The price is $178
Oct 22 - Oct 23
Total with taxes and fees
1 Bed/1 Bath Guest House
A wooden interior with a bar area featuring two stools and a countertop.

8. 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
$178 nightly
The price is $178
Nov 1 - Nov 2
Total with taxes and fees
Meadowview Guest House
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.

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.
$232 nightly
The price is $232
Oct 22 - Oct 23
Total with taxes and fees
Deer Lodge (Secluded in Amish Country and peaceful)
A cozy kitchen with wooden cabinets, a stove, and a refrigerator. There is a dining table with chairs and a window with blinds.

10. 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.
$232 nightly
The price is $232
Oct 22 - Oct 23
Total with taxes and fees
Hunter Lodge (Secluded in Amish Country and peaceful)
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, (47 reviews)
"Pictures don’t do this cabin justice - so much nicer than I was expecting!! This place is adorably decorated. Beds were comfortable. Peaceful and relaxing. Has anything you may need during stay. Definitely recommend to anyone!!"
United States
Amy C.
$232 nightly
The price is $232
Oct 22 - Oct 23
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, (26 reviews)
"This was a great stay. The property owners were fabulous. Definitely coming back ."
United States
Atonenent R.
$175 nightly
The price is $181
Oct 26 - Oct 27
Total with taxes and fees
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
A wooden interior with a kitchen area, including a microwave, sink, and cabinets.

13. The Huntsmen

The Huntsmen
Hillsboro
7.6 out of 10, Good, (7 reviews)
"A basic cabin in a good area for pets."
United States
Marcia
$116 nightly
The price is $123
Nov 16 - Nov 17
Total with taxes and fees
The Huntsmen
A wooden cabin interior with a sofa, a television, and a sliding barn door.

14. 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, (9 reviews)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
United States
Kenneth
$176 nightly
The price is $180
Oct 22 - Oct 23
Total with taxes and fees
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

15. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (26 reviews)
"Very nice stay. "
United States
Jennifer J.
$424 nightly
The price is $435
Oct 22 - Oct 23
Total with taxes and fees
Grain Bin - Unique Stay
A cabin interior with a sofa, a table, a kitchen area, and a ceiling fan.

16. 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.
$232 nightly
The price is $240
Oct 22 - Oct 23
Total with taxes and fees
Tom & Jerri's Rustic Cabin located on the lake
A dark green wooden building with a black door, a window, and a small balcony with a 'hello' mat.

17. 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.
$292 nightly
The price is $292
Oct 26 - Oct 27
Total with taxes and fees
Sunset Cabin-Adults Only Hot Tub Getaway
A rustic cabin with a wooden staircase leading to a deck, surrounded by trees and a clear sky.

18. Glamping Cabin | Huge Window | Unique Boulder Views

Glamping Cabin | Huge Window | Unique Boulder Views
Green Township
4.0 out of 10, (1 review)
$114 nightly
The price is $114
Oct 22 - Oct 23
Total with taxes and fees
Glamping Cabin | Huge Window | Unique Boulder Views
Living area

19. The Beach House

The Beach House
Hillsboro
7.8 out of 10, Good, (7 reviews)
"Perfect spot for weekend getaway "
United States
Heidi R.
$145 nightly
The price is $154
Oct 22 - Oct 23
Total with taxes and fees
The Beach 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 22 - Oct 23
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

Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky

8/10 Good
"No safety lock on door. No stopper for tub. Toliet set was way loose and lid would not stay up. It’s a nice place to stay everything needs to be updated from time to time."
John 2-night trip
Posted 2 days ago
Days Inn by Wyndham Maysville Kentucky

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 $178 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.