Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

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.
$278 nightly
The price is $306
Jun 8 - Jun 9
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.
$278 nightly
The price is $306
Jun 8 - Jun 9
Total with taxes and fees
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Property grounds

Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5

Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5
Stanton
9.4 out of 10, Exceptional, (15 reviews)
"Fun for the family!"
United States
Jennifer
$119 nightly
The price is $132
Jun 8 - Jun 9
Total with taxes and fees
Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5
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)
"Very nice area and quiet. Outside of the home looked a bit rough. Inside was clean and organized with everything you would need to be comfortable. The owner was very responsive and informative. It was a very fun stay. Stanton is a beautiful town with lots of outdoor activities. I highly recommend booking here at the Towner. We will be booking again next year."
United States
Darren
$184 nightly
The price is $209
Jun 9 - Jun 10
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, (1,912 reviews)
"Great place to stay, they have a place to eat, trails to walk and lots of nice people around."
United States
Coty jay
$126 nightly
The price is $139
Jun 14 - Jun 15
Total with taxes and fees
Natural Bridge State Resort Park
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, (107 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 10 - Jun 11
Total with taxes and fees
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
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.
$186 nightly
The price is $205
Jun 8 - Jun 9
Total with taxes and fees
Quaint, heavily forested cabin, mountain valley view.
Interior

"Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.2 out of 10, Wonderful, (14 reviews)
"Great location "
United States
Zach M.
$211 nightly
The price is $233
Jun 8 - Jun 9
Total with taxes and fees
"Rocky Top" - Cozy RRG Cabin
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.
$190 nightly
The price is $210
Jun 8 - Jun 9
Total with taxes and fees
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Smart TV, fireplace, books

Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (112 reviews)
"This is a unique property, it feels like stepping into history. It is well maintained, clean and comfortable but not your average stay! "
United States
Jennie C.
$155 nightly
The price is $180
Jun 9 - Jun 10
Total with taxes and fees
Unique Stay in a 1907 Log Cabin on The Kentucky River
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 9 - Jun 10
Total with taxes and fees
Dappled Grey Cabin with hot tub at Red River Gorge
Terrace/patio

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (130 reviews)
"Wonderful stay! Everything was clean and view was great. Thanks for a great stay! "
United States
Abby H.
$258 nightly
The price is $284
Jun 8 - Jun 9
Total with taxes and fees
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
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.
$195 nightly
The price is $226
Jun 9 - Jun 10
Total with taxes and fees
1800’s Historical Log Cabin near I-75 Interstate
Terrace/patio

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (76 reviews)
"Would stay again. Responsive host, property was very clean and host had left nice touches / decorations for valentines day weekend visit."
United States
Robert C.
$175 nightly
The price is $193
Jun 16 - Jun 17
Total with taxes and fees
Mountain Memories Cabin
Terrace/patio

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (35 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
$164 nightly
The price is $181
Jun 8 - Jun 9
Total with taxes and fees
Mountaintop Cottage
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 10 - Jun 11
Total with taxes and fees
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Outdoor spa tub

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub
Stanton
10.0 out of 10, Exceptional, (7 reviews)
"Yes, I brought my tiny dog and she loved it there as much as we did! "
United States
Kimberly J.
$297 nightly
The price is $325
Jun 8 - Jun 9
Total with taxes and fees
Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub
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.
$315 nightly
The price is $331
Jun 18 - Jun 19
Total with taxes and fees
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
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.
$246 nightly
The price is $271
Jun 8 - Jun 9
Total with taxes and fees
"Cardinal Crest" - Overlook Dome 002 in RRG
Fridge, microwave, oven, stovetop

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.
Stanton
9.6 out of 10, Exceptional, (23 reviews)
"Beautiful cabin and property, very quiet and surely secluded. Very clean and decorated, stocked well with cooking utensils. We will definitely make plans to visit again!"
United States
Kevin S.
$212 nightly
The price is $234
Jun 8 - Jun 9
Total with taxes and fees
Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.
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

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

6/10 Okay
"The property is very dated. Odd smells in the elevators & around."
Lori 2-night trip
Posted 1 hour ago
DoubleTree Suites by Hilton Hotel Lexington

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 $132 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?

Mid-Century 3 BR In Heart of Downtown Lex: Visitors like this Winchester vacation home rental. It is located in the city center and has a patio, a selection of games, 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.

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?

Winchester Traveling Trail and Lykins Park are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Winchester Opera House and Clark County Courthouse 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.