Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winchester vacation rentals

Interior

Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?
West Union
10.0 out of 10, Exceptional, (9 reviews)
"Very clean cabin and very cozy!"
United States
Debbie F.
$155 nightly
The price is $161
Feb 14 - Feb 15
Total with taxes and fees
Bear Necessities Cabin - What Else Do You Need?
Property grounds

Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.8 out of 10, Exceptional, (8 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
Feb 15 - Feb 16
Total with taxes and fees
Glamping Cabin | Huge Window | Over a Creek
Property grounds

Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
10.0 out of 10, Exceptional, (2 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
Feb 15 - Feb 16
Total with taxes and fees
Glamping Cabin | Huge Window | Cliff and Animal Views
Interior

Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful
Peebles
9.8 out of 10, Exceptional, (27 reviews)
"Excellent place "
United States
Casey J.
$183 nightly
The price is $183
Feb 15 - Feb 16
Total with taxes and fees
Secluded in Amish Country and peaceful
Interior

Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.4 out of 10, Exceptional, (20 reviews)
"Clean & cool little place."
United States
Stephen
$198 nightly
The price is $206
Feb 14 - Feb 15
Total with taxes and fees
Cowboy Saloon Cabin
Fridge, microwave, oven

Country Cabin in Amish Country

Country Cabin in Amish Country
Peebles
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful clean place "
United States
Casey J.
$183 nightly
The price is $189
Feb 15 - Feb 16
Total with taxes and fees
Country Cabin in Amish Country
Property grounds

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
9.0 out of 10, Wonderful, (19 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
Feb 15 - Feb 16
Total with taxes and fees
Glamping Cabin | Huge Window | Tree House Feel
Smart TV

The Angler

The Angler
Hillsboro
8.4 out of 10, Very Good, (10 reviews)
"Clean and great for a couple of fisherman enjoying the lake and surrounding area. "
United States
Jerry P.
$120 nightly
The price is $127
Feb 16 - Feb 17
Total with taxes and fees
The Angler
Outdoor spa tub

White Oak Cottage Sleeps 4

White Oak Cottage Sleeps 4
Georgetown
9.2 out of 10, Wonderful, (9 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.
$178 nightly
The price is $178
Feb 16 - Feb 17
Total with taxes and fees
White Oak Cottage Sleeps 4
Exterior detail

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, (23 reviews)
"Just had a few hiccups but all in all it was a great time."
United States
Amber B.
$186 nightly
The price is $194
Feb 18 - Feb 19
Total with taxes and fees
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
Fridge, microwave, oven, stovetop

Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (31 reviews)
"Our work crew stayed here while in the area. It was perfect and cozy. Hosts were very responsive to any needs or questions!"
United States
April H.
$228 nightly
The price is $239
Mar 2 - Mar 3
Total with taxes and fees
Griffis Game Hunting and/or Getaway
Living area

The White Stag

The White Stag
Hillsboro
7.4 out of 10, Good, (8 reviews)
"We CD enjoyed our stay. It was spacious and cozy. The large bed is very tall so take a step stool. Mattresess are very confy. "
United States
Danelia
$133 nightly
The price is $141
Feb 16 - Feb 17
Total with taxes and fees
The White Stag
Terrace/patio

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.
Adams County
9.8 out of 10, Exceptional, (29 reviews)
"Great location. "
United States
John S.
$349 nightly
The price is $364
Feb 19 - Feb 20
Total with taxes and fees
Peaceful cabin with spectacular river and scenic views.
Outdoor spa tub

Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (22 reviews)
"I was out there for a wedding and this place was great for a weekend trip."
United States
L
$192 nightly
The price is $192
Feb 15 - Feb 16
Total with taxes and fees
Meadowview Guest House
Terrace/patio

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
6.8 out of 10, (3 reviews)
"Yes, it would have been perfect for leashed pets. Cabin was very cozy and fit our needs well. One thing we did notice that would've been great if they had some bowls for mixing pancakes and such. "
United States
Dane C.
$155 nightly
The price is $155
Feb 15 - Feb 16
Total with taxes and fees
Sleeps 4| Private Bathroom | Stunning Views
Microwave, oven, stovetop

The Huntsmen

The Huntsmen
Hillsboro
7.0 out of 10, Good, (2 reviews)
"Very clean, not super easy to understand check in instructions "
United States
Jacob U.
$109 nightly
The price is $115
Feb 14 - Feb 15
Total with taxes and fees
The Huntsmen
Interior

Tom & Jerri's Rustic Cabin located on the lake

Tom & Jerri's Rustic Cabin located on the lake
Hamersville
10.0 out of 10, Exceptional, (13 reviews)
"Very cute cabin on the lake! Great stay while at the ball fields! "
United States
Malia P.
$220 nightly
The price is $229
Feb 17 - Feb 18
Total with taxes and fees
Tom & Jerri's Rustic Cabin located on the lake
Property grounds

Sleeps 12| Private Bathroom | Stunning Views

Sleeps 12| Private Bathroom | Stunning Views
Blue Creek
10.0 out of 10, Exceptional, (7 reviews)
"This cabin was exactly what we were looking for: Cozy, peaceful, clean, comfortable and all the amenities. Located near several great hiking spots within a short drive. Great indoor and outdoor space. Host was very friendly and responsive. Highly recommend this place!"
United States
Amy H.
$313 nightly
The price is $313
Feb 15 - Feb 16
Total with taxes and fees
Sleeps 12| Private Bathroom | Stunning Views
Exterior

Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream
Green Township
9.8 out of 10, Exceptional, (9 reviews)
"We had a spectacular stay! Comfortable, Quiet, and Clean!Only a small suggestion Put a handle on the inside of the screen door and WD-40 the big door on cabin 1."
United Kingdom
Abby M.
$114 nightly
The price is $114
Feb 16 - Feb 17
Total with taxes and fees
Glamping Cabin | Huge Window | Nature Lovers Dream
Exterior

Glamping Cabin | Huge Window | Valley and Cliff Views

Glamping Cabin | Huge Window | Valley and Cliff Views
Green Township
10.0 out of 10, Exceptional, (2 reviews)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
$114 nightly
The price is $114
Feb 15 - Feb 16
Total with taxes and fees
Glamping Cabin | Huge Window | Valley and Cliff Views
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

10/10 Excellent
"100 % muy bueno "
Sabrina 1-night trip
Posted 5 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 $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?

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events: Visitors like this Winchester vacation home rental. It comes with laundry facilities so you can feel at home during your trip. Kitchen amenities like a dishwasher and a stovetop can make your vacation run smoothly.

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.