Winchester Vacation Rentals

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Vacation Rentals in Winchester

Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (238)
"Very well stocked cabin had everything we needed. Love the fireplace and fishing lake!"
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Fridge, microwave, oven, stovetop
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
10.0 out of 10, Exceptional, (94)
"The cabin was beautiful and the cleanest place we have ever rented. Very well stocked, wonderful outdoor space. The host was very friendly, quickly responsive to any needs or questions. We really enjoyed our stay and hope to go back."
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Fridge, microwave, oven, stovetop
The Bear Den (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (16)
"Everything was wonderful!"
The price is $105
$171 total
includes taxes & fees
May 19 - May 20
The Bear Den (Secluded in Amish Country and peaceful)
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
Secluded cabin located in Amish country
10.0 out of 10, Exceptional, (64)
"We had a relaxing few days at this beautiful cabin. It was an awesome space both inside and out, and we hope to stay again next time we’re in the area."
Secluded cabin located in Amish country
Oven, stovetop, dishwasher
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
10.0 out of 10, Exceptional, (12)
"We had a great weekend. The owner was very responsive and the house and property was beautiful."
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Smart TV, fireplace, DVD player, stereo
Cozy private getaway built for couples to reconnect !!
10.0 out of 10, Exceptional, (12)
"This property is beautiful...peaceful...perfect. The pictures are an accurate reflection of the property but being there in person makes the pictures seem lacking. The house is just lovely and cozy and modern...clean and comfortable too! I love the decor - fresh and inviting as well as calming and cozy. The kitchen is amazing for such a quaint home. The hot tub was incredible at the end of a busy and tiring day! The home was fully stocked so no need to worry about bringing extra stuff. And the...
Cozy private getaway built for couples to reconnect !!
Property grounds
Beautiful Rocky Fork 2BR Cozy Cottage
10.0 out of 10, Exceptional, (86)
"Really nice place to stay, close to lake."
Beautiful Rocky Fork 2BR Cozy Cottage
Property grounds
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (306)
"We enjoyed the Behm mountain cabin so much we already booked a return in October!"
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
Property grounds
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
10.0 out of 10, Exceptional, (55)
"Our 2nd Fall stay here and another great time!! 16 guys and plenty of room for all. Great yard space for cornhole & can jam. Love the fire ring. Some rain our last night, but plenty of room inside for card games. GREAT PLACE!! GREAT DEAL!!"
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Property grounds
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
10.0 out of 10, Exceptional, (9)
"This place was exactly what we were looking for! It was very private and had a beautiful view facing the woods. We took our 4 little boys and enjoyed going on walks in the woods and playing in the creek. The hot tub was nice to relax in once the kids were in bed. It was very clean and had everything we needed that included a fully stocked kitchen, camping chairs, firewood and fire starter. Cindy and Ken were easy to communicate with, very hospitable and friendly. We will definitely be coming...
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Spa
Rustic Lodge with private cabins / 6 person hot tub and camp fire
10.0 out of 10, Exceptional, (21)
"The home is Beautiful. Everything a family needs is there. Board games, darts, karaoke, corn hole, and steaming TV services. The location is convenient to local attractions. The two individual cabins are very cozy and well appointed. We had a couple small issues that the hosts took care of immediately. A bathroom in the upstairs of the home would be a great addition. We would highly recommend this property."
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Marina
Hunter Lodge (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (17)
"We enjoyed our stay at Hunter Lodge. Cabin was clean and comfortable. Great place to stay while hiking in the area."
The price is $105
$171 total
includes taxes & fees
May 19 - May 20
Hunter Lodge (Secluded in Amish Country and peaceful)
3 bedrooms, desk, iron/ironing board, WiFi
Beautifully renovated 3BR house w/lake views
10.0 out of 10, Exceptional, (16)
"Perfect size and location for our getaway. The gameroom was great for the kids, great fire pit for the adults. Close to all that Rocky Fork has to offer."
Beautifully renovated 3BR house w/lake views
Exterior
Tom & Jerri's Rustic Cabin located on the lake
10.0 out of 10, Exceptional, (7)
"Everything was just as listed and very nice and comfortable. Pamela was an excellent host. She promptly answered all my questions."
The price is $155
$204 total
includes taxes & fees
May 19 - May 20
Tom & Jerri's Rustic Cabin located on the lake
Exterior
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
10.0 out of 10, Exceptional, (8)
"Amazing property. Has everything you'd want in a rental."
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
2 bedrooms, bed sheets
SPECIAL PROMO! on 2 bdrm Amish-built cabin, pond access and private dock.
10.0 out of 10, Exceptional, (10)
"Quiet. Peaceful. Stunning sunset and sunrise views. Close to good hiking including Quiveringhearts. The owner was delightfully accessible as was her employee. The cats were a handful but we got used to them. They calmed down after they were fed understandably!"
SPECIAL PROMO! on 2 bdrm Amish-built cabin, pond access and private dock.
1 bedroom, bed sheets
SPECIAL PROMO! on Private cabin on 80 acre farm in Adams County Ohio
10.0 out of 10, Exceptional, (6)
"We had a lovely time in this cozy cabin. Just what we needed to unplug and unwind for a delightful weekend. Hosts were communicative and helpful and we will likely stay again if we come to the area."
SPECIAL PROMO! on Private cabin on 80 acre farm in Adams County Ohio
Exterior
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (88)
"Another wonderful stay! Our 3rd time visiting and love it more and more. Very clean, beautifully decorated and just a great place to relax for the weekend. We enjoy building memories here and our kids beg to go back regularly. Thank you for creating such a special place!"
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
Fridge, microwave, oven, stovetop
Peaceful Country Retreat 20 acres Private Pond
10.0 out of 10, Exceptional, (14)
"my family and i had a great stay plenty of room for everyone. if you're looking for a quiet getaway this is the place you want to be."
Peaceful Country Retreat 20 acres Private Pond
Property grounds
URBAN GETAWAY - .6 Downtown Maysville/Entire House
9.8 out of 10, Exceptional, (15)
"The property was great! Good location for me."
The price is $79
$121 total
includes taxes & fees
Jun 10 - Jun 11
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Don't see what you're looking for?
See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (238)
"Very well stocked cabin had everything we needed. Love the fireplace and fishing lake!"
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Front of property
French Quarter Inn
3.0 star property
8.8 out of 10, Excellent, (620)
"Reception staff were excellent! Very friendly and helpful. Easy to walk to many restaurants and important sites. The site lists continental breakfast but it was much more than that."
The price is $99
$110 total
includes taxes & fees
May 19 - May 20
French Quarter Inn
Fridge, microwave, oven, stovetop
Working Dairy Goat Farm - Glamping in RV Camper in Luxury - Deer Hunters Welcome
8.0 out of 10, Very Good, (4)
"We couldn't have asked for a better experience. Judy and her husband were more than accommodating, they provided a great experience for my six year old. We were able to fish, play with goats, see chickens, ducks, and turkeys. We even were able to swim! In the evening they provided us with dinner around a campfire where we roasted s'mores and my son was able to play with other kids around his age. We also got to experience Amish country nearby which even included a zoo to check out! On our last...
The price is $139
$179 total
includes taxes & fees
May 17 - May 18
Working Dairy Goat Farm - Glamping in RV Camper in Luxury - Deer Hunters Welcome
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.

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 $69 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.

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?

Beautiful Rocky Fork 2BR Cozy Cottage: You might want to consider this vacation home rental near Winchester, which is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Winchester?

While you're exploring the area, Adams Lake State Park and Rocky Fork Lake State Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Serpent Mound and Rocky Fork State Park.

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.

Recent reviews of Winchester properties
Expedia verified reviews

Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky

5/5 Excellent
"Very nice staff"
A verified traveler stayed at Days Inn by Wyndham Maysville Kentucky
Posted 4 days ago
Days Inn by Wyndham Maysville Kentucky