Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Winchester vacation rentals

Exterior

Vacation Home in Winchester

River Relaxation - Calm Riverfront Home in Winchester Kentucky
7.0 out of 10, Good, (4 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.
$283 nightly
The price is $311
Jan 26 - Jan 27
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Property grounds

Camping in Stanton

Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
10.0 out of 10, Exceptional, (24 reviews)
"Will definitely stay again. Next time will be with our kiddos. "
United States
Alexandra
$123 nightly
The price is $136
Jan 27 - Jan 28
Total with taxes and fees
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
Fridge, microwave, oven, stovetop

Mobile Home in Stanton

Conveniently Located ~ WiFi ~ Central Heat & Air.
9.8 out of 10, Exceptional, (47 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
$143 nightly
The price is $162
Jan 28 - Jan 29
Total with taxes and fees
Conveniently Located ~ WiFi ~ Central Heat & Air.
Property grounds

Mobile Home in Stanton

Relaxing, cozy cabin in the heart of the Red River Gorge!
10.0 out of 10, Exceptional, (128 reviews)
"Wonderful stay!! So close to red river gorge! Was packed with anything you would need for a great stay!!! "
United States
Julie S.
$198 nightly
The price is $218
Jan 26 - Jan 27
Total with taxes and fees
Relaxing, cozy cabin in the heart of the Red River Gorge!
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

Cabin in Slade

Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1,795 reviews)
"Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay."
United States
Kimberly
$86 nightly
The price is $95
Jan 28 - Jan 29
Total with taxes and fees
Natural Bridge State Resort Park
House (1 Bedroom) | Interior

Cottage in Frenchburg

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
3.0 star property
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
$236 nightly
The price is $262
Jan 25 - Jan 26
Total with taxes and fees
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
TV, fireplace

Cabin in Stanton

Dappled Grey Cabin with hot tub at Red River Gorge
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
$162 nightly
The price is $170
Jan 25 - Jan 26
Total with taxes and fees
Dappled Grey Cabin with hot tub at Red River Gorge
Property grounds

Cabin in Slade

Quaint, heavily forested cabin, mountain valley view.
8.2 out of 10, Very Good, (28 reviews)
"Cabin was good but other cabins are close cabin was very comfortable road to cabin is very steep but doable "
United States
Terry
$185 nightly
The price is $204
Jan 25 - Jan 26
Total with taxes and fees
Quaint, heavily forested cabin, mountain valley view.
Interior

Cabin in Stanton

Hot Tub! Tiny Cabin Retreat near RRG
8.0 out of 10, Very Good, (11 reviews)
"Nice calm and nice cabin and was cozy I had fun for my birthday overall great experience "
United States
MainSlime
$161 nightly
The price is $178
Jan 25 - Jan 26
Total with taxes and fees
Hot Tub! Tiny Cabin Retreat near RRG
Property grounds

Cabin in Stanton

Hot Tub! Tiny House Retreat in the Woods
7.2 out of 10, Good, (5 reviews)
"Overall, great stay! The tiny house looked just like the photos and the hot tub was added relaxation. Lots of hiking options in the area that we were able to explore!The only heads up would be that the drive back to the cabin is gravel, bumpy, and mainly uphill…so if you don’t have a vehicle that can handle it, it could be tricky. Our Jeep made it just fine though!"
United States
Jaimie K.
$164 nightly
The price is $181
Jan 25 - Jan 26
Total with taxes and fees
Hot Tub! Tiny House Retreat in the Woods
Exterior

Apartment in Richmond

Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
9.8 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay. Location was amazing for our trip!"
United States
Deanna E.
$205 nightly
The price is $226
Jan 25 - Jan 26
Total with taxes and fees
Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
Terrace/patio

Cottage in Stanton

Mountaintop Cottage
10.0 out of 10, Exceptional, (27 reviews)
"I cannot say enough how CUTE this was we were so happy we found it. Loved the animals and will definitely stay again."
United States
Jessica H.
$175 nightly
The price is $193
Jan 31 - Feb 1
Total with taxes and fees
Mountaintop Cottage
Exterior

Cabin in Stanton

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
9.8 out of 10, Exceptional, (16 reviews)
"Overall the cabin was very nice. There were some minor maintenance issues, such as the electric fireplace not working and the remotes for the tv needing batteries, but it was a great cabin. We enjoyed our stay. "
United States
Anonymous traveler
$329 nightly
The price is $363
Jan 25 - Jan 26
Total with taxes and fees
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
Fridge, microwave, oven, stovetop

Apartment in Richmond

Modern 2bd 2ba - Near I75, No Steps, Free Wifi
9.8 out of 10, Exceptional, (85 reviews)
"Clean, close to campus . Would definitely stay again. "
United States
Christina K.
$181 nightly
The price is $197
Jan 25 - Jan 26
Total with taxes and fees
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Smart TV

Vacation Home in Lexington

My Old Kentucky Home
10.0 out of 10, Exceptional, (27 reviews)
"Cool property, with a great location. Owner had great communication."
United States
Anonymous traveler
$213 nightly
The price is $247
Jan 25 - Jan 26
Total with taxes and fees
My Old Kentucky Home
2 bedrooms, free WiFi, bed sheets

Apartment in Downtown Lexington

This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
9.4 out of 10, Exceptional, (13 reviews)
"Everything was great. The location was wonderful. The apartment had everything we needed."
United States
Melissa H.
$217 nightly
The price is $221
Jan 25 - Jan 26
Total with taxes and fees
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Terrace/patio

Vacation Home in Stanton

Peregrine Cabin - Off the Grid, hike-in cabin
10.0 out of 10, Exceptional, (13 reviews)
"We absolutely loved being tucked into the woods. We had a great experience and it was the perfect trip for our anniversary. "
United States
Kenetra F.
$161 nightly
The price is $175
Jan 26 - Jan 27
Total with taxes and fees
Peregrine Cabin - Off the Grid, hike-in cabin
Property grounds

Cabin in Irvine

Secluded & Tranquil Cabin ~ Near Red River Gorge
10.0 out of 10, Exceptional, (58 reviews)
"Super cozy and quaint. Loved that it had two bathrooms. Kitchen was very well appointed. Outdoor space and grilling area was fantastic. Really nice and well kept property. "
United States
Joel R.
$235 nightly
The price is $259
Jan 25 - Jan 26
Total with taxes and fees
Secluded & Tranquil Cabin ~ Near Red River Gorge
Interior

Cabin in Stanton

"Rocky Top" - Cozy RRG Cabin
9.2 out of 10, Wonderful, (13 reviews)
"Great place to stay! Super close to RRG and the DBBB. Also just a few minutes for Miguel’s for the BEST pizza!"
United States
Mallory H.
$178 nightly
The price is $196
Jan 27 - Jan 28
Total with taxes and fees
"Rocky Top" - Cozy RRG Cabin
TV, video games

Cabin in Stanton

Pilot Point- Hot Tub, Pet Friendly, Firepit, Covered Deck
9.6 out of 10, Exceptional, (163 reviews)
"Cabin was adorable. It was the perfect getaway for my husband and me. "
United States
Danielle
$230 nightly
The price is $255
Jan 25 - Jan 26
Total with taxes and fees
Pilot Point- Hot Tub, Pet Friendly, Firepit, Covered Deck
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Loved this stay! This hotel is adorable and great staff! "
Sierra 2-night trip
Posted 3 days ago
Elwood Hotel & Suites

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 $95 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?

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.: You might want to consider this vacation home rental near Winchester, which is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge to make your meal-planning easier.

How many vacation rentals are there in Winchester?

Expedia has 6 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

College Park and GRCHS Baseball Field 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.