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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester vacation rentals

A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs.

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
$679 nightly
The price is $697
Nov 16 - Nov 17
Total with taxes and fees
Quiet Farm Escape | Fishing, Nature & Views
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.

2. 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.
$213 nightly
The price is $222
Nov 15 - Nov 16
Total with taxes and fees
Country Cabin in Amish Country
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.

3. 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.
$213 nightly
The price is $213
Nov 15 - Nov 16
Total with taxes and fees
Deer Lodge (Secluded in Amish Country and peaceful)
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, (40 reviews)
"Such a cute place!! We didn’t stay at the house enough to enjoy all of the amenities, but the cabin was very clean and cozy. The beds are really comfortable. The host was great too!"
United States
Daisha M.
$192 nightly
The price is $202
Nov 16 - Nov 17
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 cabin in the heart of Amish Country and hiking

“Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking
West Union
10.0 out of 10, Exceptional, (4 reviews)
"The residence was impeccably, clean and well thought out for provisions as far as cooking utensils and daily living things a person needs I highly recommend"
United States
William G.
$203 nightly
The price is $215
Dec 14 - Dec 15
Total with taxes and fees
“Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking
A hot tub in a backyard with a wooden fence and a grassy field in the background.

6. Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (30 reviews)
"Great stay. Host was quick to respond to all questions. Every detail was thought through. Highly recommend staying here!"
United States
Kayla E.
$167 nightly
The price is $167
Nov 15 - Nov 16
Total with taxes and fees
Meadowview Guest House
A small cabin with a wooden exterior, a porch, and a visible interior with a bed and a table.

7. 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.
$106 nightly
The price is $106
Nov 15 - Nov 16
Total with taxes and fees
Glamping Cabin | Huge Window | Valley and Cliff Views
A kitchen with wooden cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

8. 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.
$213 nightly
The price is $213
Nov 15 - Nov 16
Total with taxes and fees
Secluded in Amish Country and peaceful
A cozy cabin interior with a wooden ceiling, a fireplace, a bar area with stools, and a television mounted on the wall.

9. Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.6 out of 10, Exceptional, (28 reviews)
"Place was great we had a great time relaxing and we loved the fire pit and how they provided the wood"
United States
Anthony R.
$168 nightly
The price is $175
Nov 15 - Nov 16
Total with taxes and fees
Cowboy Saloon Cabin
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.
$223 nightly
The price is $223
Nov 17 - Nov 18
Total with taxes and fees
Hunter Lodge (Secluded in Amish Country and peaceful)
A rustic wooden structure with a wooden deck leading to a warmly lit interior, surrounded by trees.

11. 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 great relaxing time everything was as expected."
United States
brandon b.
$106 nightly
The price is $106
Nov 15 - Nov 16
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.

12. 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
$151 nightly
The price is $163
Nov 16 - Nov 17
Total with taxes and fees
1 Bed/1 Bath Guest House
A wooden interior with a round dining table, chairs, a welcome sign, and a window with a view.

13. 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, (49 reviews)
"Great cabin. Very clean, fully stocked kitchen, owner is very helpful."
United States
Christy A.
$223 nightly
The price is $223
Nov 17 - Nov 18
Total with taxes and fees
The Bear Den (Secluded in Amish Country and peaceful)
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

14. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (26 reviews)
"Very nice stay. "
United States
Jennifer J.
$403 nightly
The price is $414
Nov 16 - Nov 17
Total with taxes and fees
Grain Bin - Unique Stay
A wooden cabin room with a bed, checkered bedding, a nightstand with a lamp, and a window with a view of trees.

15. Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
8.6 out of 10, Excellent, (23 reviews)
"The experience was amazing had a wonderful view and privacy I didn't have phone reception so I couldn't communicate very well. It was an adventure and we loved it so much that we are coming back to celebrate our 30th anniversary anniversary"
United States
Tonya U.
$106 nightly
The price is $106
Nov 26 - Nov 27
Total with taxes and fees
Glamping Cabin | Huge Window | Tree House Feel
A wooden deck with two Adirondack chairs and a small table, overlooking a green landscape.

16. 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.
$166 nightly
The price is $172
Nov 16 - Nov 17
Total with taxes and fees
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
An outdoor patio area with a stone fire pit, a hot tub, and outdoor seating.

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.
$264 nightly
The price is $264
Nov 17 - Nov 18
Total with taxes and fees
Sunset Cabin-Adults Only Hot Tub Getaway
A cozy living room with a brown sofa, patterned armchairs, a coffee table, and a television.

18. The Angler

The Angler
Hillsboro
8.6 out of 10, Excellent, (16 reviews)
"Clean and great for a couple of fisherman enjoying the lake and surrounding area. "
United States
Jerry P.
$112 nightly
The price is $119
Dec 3 - Dec 4
Total with taxes and fees
The Angler
A wooden cabin interior with a four-poster bed, a fireplace, a dining table, and a sofa.

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

Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
West Union
$277 nightly
The price is $303
Dec 2 - Dec 3
Total with taxes and fees
Cabin 5 M.Y. Cabin - Includes a Homemade Country Breakfast!
A wooden deck with outdoor furniture, a barbecue grill, and a view of a lake.

20. 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, (16 reviews)
"Very cute cabin on the lake! Great stay while at the ball fields! "
United States
Malia P.
$211 nightly
The price is $219
Nov 15 - Nov 16
Total with taxes and fees
Tom & Jerri's Rustic Cabin located on the lake
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

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.

10/10 Excellent
"Beautiful property and a great view of the river and Maysville."
Dave k. 2-night trip
Posted 2 days ago
Peaceful cabin with spectacular river and scenic views.

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 $106 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?

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.