MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Winchester vacation rentals

The Winchester

The Winchester
Winchester
8.4 out of 10, Very Good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
$280 nightly
The price is $308
Jun 14 - Jun 15
Total with taxes and fees
The Winchester
Fridge, microwave, oven, stovetop

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.8 out of 10, Exceptional, (9 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
$280 nightly
The price is $308
Jun 14 - Jun 15
Total with taxes and fees
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Exterior

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.6 out of 10, Good, (5 reviews)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
$346 nightly
The price is $381
Jun 15 - Jun 16
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Fridge, microwave, oven, stovetop

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (50 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
$188 nightly
The price is $213
Jun 21 - Jun 22
Total with taxes and fees
Conveniently Located ~ WiFi ~ Central Heat & Air.
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,924 reviews)
"Great area Nice place to stay"
United States
Julie
$131 nightly
The price is $144
Jun 14 - Jun 15
Total with taxes and fees
Natural Bridge State Resort Park
House (1 Bedroom) | Interior

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveler
$308 nightly
The price is $339
Jun 14 - Jun 15
Total with taxes and fees
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Property grounds

Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.2 out of 10, Very Good, (33 reviews)
"Beautiful little cabin"
United States
Ryan W.
$188 nightly
The price is $207
Jun 16 - Jun 17
Total with taxes and fees
Quaint, heavily forested cabin, mountain valley view.
Property grounds

Spacious Secluded Cabin on 100 Acres Near Red River Gorge

Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (76 reviews)
"Secluded cabin - we loved the quiet "
United States
Scot
$238 nightly
The price is $262
Jun 14 - Jun 15
Total with taxes and fees
Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Interior

East Suite-🕊️ at Bleubird Studio, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Georgetown
10.0 out of 10, Exceptional, (65 reviews)
"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "
United States
l v.
$204 nightly
The price is $225
Jun 14 - Jun 15
Total with taxes and fees
East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Smart TV, video games, DVD player, table tennis

Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!

Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
Stanton
10.0 out of 10, Exceptional, (14 reviews)
"Biggie cabin was perfect, and great location! Would absolutely stay there again! "
United States
Greg J.
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
Fridge, microwave, stovetop, dishwasher

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (12 reviews)
"Fun place to stay for 2!"
United States
Bob R.
$310 nightly
The price is $339
Jun 14 - Jun 15
Total with taxes and fees
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Interior

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Stanton
10.0 out of 10, Exceptional, (366 reviews)
"Great spot for weekend getaway. "
United States
Liz A.
$264 nightly
The price is $291
Jun 21 - Jun 22
Total with taxes and fees
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Outdoor dining

Secluded cabin in Red River Gorge with a Hot Tub and wi-fi

Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Stanton
8.6 out of 10, Excellent, (61 reviews)
"Very cozy and an amazing stay!"
United States
Sam P.
$316 nightly
The price is $332
Jun 14 - Jun 15
Total with taxes and fees
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Terrace/patio

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (46 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
$191 nightly
The price is $211
Jun 14 - Jun 15
Total with taxes and fees
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
1 bedroom, iron/ironing board, travel crib, WiFi

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Very quiet, cozy and a nice place to come back to after a long day of physical activity! "
United States
Gregory L.
$233 nightly
The price is $257
Jun 17 - Jun 18
Total with taxes and fees
"Cardinal Crest" - Overlook Dome 002 in RRG
Interior

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Stanton
10.0 out of 10, Exceptional, (324 reviews)
"Great stay! Loved the private driveway. "
United States
Emily N.
$253 nightly
The price is $279
Jun 21 - Jun 22
Total with taxes and fees
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
TV, fireplace

Dappled Grey Cabin with hot tub at Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"
United States
Jessica
$170 nightly
The price is $175
Jun 17 - Jun 18
Total with taxes and fees
Dappled Grey Cabin with hot tub at Red River Gorge
Smart TV, fireplace, books

1800’s Historical Log Cabin near I-75 Interstate

1800’s Historical Log Cabin near I-75 Interstate
Lexington
9.4 out of 10, Exceptional, (69 reviews)
"Excellent stopover. "
United States
Robert W.
$210 nightly
The price is $244
Jun 16 - Jun 17
Total with taxes and fees
1800’s Historical Log Cabin near I-75 Interstate
Fridge, microwave, oven, stovetop

Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Richmond
9.8 out of 10, Exceptional, (88 reviews)
"Everything was fantastic!!"
United States
Leah Anne G.
$209 nightly
The price is $228
Jun 14 - Jun 15
Total with taxes and fees
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Property grounds

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (108 reviews)
"This was a wonderful location and a delightfully cozy cabin for a couple or a solo stay. Might very well stay here again in the future."
United States
Jason H.
$175 nightly
The price is $193
Jun 21 - Jun 22
Total with taxes and fees
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
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

Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

10/10 Excellent
"The staff was nice and helpful. I liked where the hotel was located. I liked that it wasn’t in a crowded area but close enough to town. The beds were comfortable and I slept really well. We stayed in a room on the first floor with courtyard view, and if there are people out there hanging out, playing corn hole or the other game they have you can kind of hear them, but I had my fan to drown them out. I would stay again."
Abigail 3-night trip
Posted 1 hour ago
Hotel LEX, Trademark Collection by Wyndham

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 $136 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

Are there vacation rentals in Winchester?

Yes, we offer vacation rentals close to top points of interest in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Our travelers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffeehouses and shopping during your trip.

What are some of the best vacation home rentals that Winchester has to offer?

Near Kentucky State Horse Park 💛The Yalla House🚪 🏇🏼Horse & Bourbon Central🥃: Visitors like this Winchester vacation home rental. It is located in a rural location and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Winchester?

Expedia has 5 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Community Park and The Holler are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Wiseman Park and Winchester Traveling Trail are other places to visit while you're in town.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.