An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. 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, (12 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
$265 nightly
The price is $292
Sep 21 - Sep 22
Total with taxes and fees
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A black leather sofa with a center console, a glass table, and two boxes on the table.

2. The Winchester

The Winchester
Winchester
8.6 out of 10, Excellent, (11 reviews)
"The house was clean and had all amenities needed. Love the location and was adorable. Wish I could have stayed longer. Love that there is a park across the street and the neighbors were very friendly"
United States
Gina
$265 nightly
The price is $292
Sep 21 - Sep 22
Total with taxes and fees
The Winchester
Exterior

3. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.8 out of 10, Good, (6 reviews)
"Good communication, great location and peaceful! Back deck to River does need a little work but it was overall a good stay! "
United States
Polly H.
$403 nightly
The price is $444
Oct 12 - Oct 13
Total with taxes and fees
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

4. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,060 reviews)
"Great place to stay."
United States
Monty
$111 nightly
The price is $122
Sep 27 - Sep 28
Total with taxes and fees
Natural Bridge State Resort Park
Property grounds

5. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (23 reviews)
"Great stay as usual. Owners are super friendly & helpful. This was our 3rd time staying as we've made this our regular when visiting family in the area."
United States
Brittany K.
$113 nightly
The price is $125
Sep 23 - Sep 24
Total with taxes and fees
Cozy, Bright Home in Historic Downtown
Microwave, oven, stovetop

6. Modern Studio - Stylish Apartment in Downtown Lexington

Modern Studio - Stylish Apartment in Downtown Lexington
Lexington
9.6 out of 10, Exceptional, (13 reviews)
"very clean & great location"
United States
BJ F.
$165 nightly
The price is $192
Sep 22 - Sep 23
Total with taxes and fees
Modern Studio - Stylish Apartment in Downtown Lexington
Dining

7. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (348 reviews)
"It felt like home during our stay! Friendly staff made us feel welcome."
United States
Anonymous traveler
$61 nightly
The price is $67
Sep 22 - Sep 23
Total with taxes and fees
2 Full Beds | Non-Smoking, Micfridge
Smart TV, fireplace, books

8. 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)
"Cabin was very unique, and charming. Had everything we needed. Steps a little wonky but easy to get through. Would definitely stay again. "
United States
Anonymous traveler
$163 nightly
The price is $189
Sep 21 - Sep 22
Total with taxes and fees
Unique Stay in a 1907 Log Cabin on The Kentucky River
Exterior

9. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (16 reviews)
"We loved staying at this super lovely little house! It was perfect for two people, everything we needed and great location! If we ever plan a trip to Lexington- this is absolutely where we will stay!"
Canada
Renae
$194 nightly
The price is $225
Sep 21 - Sep 22
Total with taxes and fees
Cozy 1-bedroom in Lexington
Property grounds

10. 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, (127 reviews)
"The cabin was clean and just what we needed for our weekend trip."
United States
Emmalynn P.
$173 nightly
The price is $191
Sep 21 - Sep 22
Total with taxes and fees
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Exterior

11. Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3

Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3
Stanton
9.6 out of 10, Exceptional, (18 reviews)
"We really enjoyed our stay. Definitely recommend!"
United States
Misty B.
$119 nightly
The price is $132
Sep 21 - Sep 22
Total with taxes and fees
Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3
Dining

12. Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (55 reviews)
"Clean, well stocked and comfortable. I always enjoy my stay here. "
United States
Robert T.
$153 nightly
The price is $168
Sep 22 - Sep 23
Total with taxes and fees
Luxury on Main / South
1 bedroom, iron/ironing board, WiFi, bed sheets

13. Westfield Blue

Westfield Blue
Richmond
9.4 out of 10, Exceptional, (11 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
$144 nightly
The price is $159
Sep 21 - Sep 22
Total with taxes and fees
Westfield Blue
Smart TV, fireplace, books

14. 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, (77 reviews)
"The property is so cool! It has so much history within it. We loved just walking around and looking at the small details. It was cozy and comfy. The property was easy to find and we were given clear instructions for check in and such."
United States
Sarah
$210 nightly
The price is $244
Sep 21 - Sep 22
Total with taxes and fees
1800’s Historical Log Cabin near I-75 Interstate
Coffee/tea maker, fridge, microwave, oven

15. Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (52 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
$200 nightly
The price is $227
Sep 21 - Sep 22
Total with taxes and fees
Conveniently Located ~ WiFi ~ Central Heat & Air.
Outdoor dining

16. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (41 reviews)
"Great spot, great location, great host."
United States
Jill
$135 nightly
The price is $156
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Exterior detail

17. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (92 reviews)
"Great place to stay!"
United States
Anna C.
$136 nightly
The price is $158
Sep 21 - Sep 22
Total with taxes and fees
Treetops Solar Sanctuary
TV

18. This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Lexington
8.8 out of 10, Excellent, (16 reviews)
"Great location and very clean. "
United States
Andrew K.
$173 nightly
The price is $176
Sep 21 - Sep 22
Total with taxes and fees
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Living area

19. 3 Miles Hollerwood/ATV Parking/Mountain Views

3 Miles Hollerwood/ATV Parking/Mountain Views
Zoe
9.8 out of 10, Exceptional, (9 reviews)
"Remote and nice location with plenty of room. "
United States
Keith P.
$224 nightly
The price is $247
Sep 21 - Sep 22
Total with taxes and fees
3 Miles Hollerwood/ATV Parking/Mountain Views
Property grounds

20. Larkspur Cabin with Hot Tub near Red River Gorge

Larkspur Cabin with Hot Tub near Red River Gorge
Stanton
9.8 out of 10, Exceptional, (11 reviews)
"My wife and I had a very relaxing get away. Lovely place for a couple."
United States
Anonymous traveler
$135 nightly
The price is $138
Sep 23 - Sep 24
Total with taxes and fees
Larkspur Cabin with Hot Tub 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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Great hotel close to UK."
Ted 1-night trip
Posted 5 hours 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 $67 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?

Luxe Home Downtown - Sleeps 6. Off-street parking: Visitors like this Winchester vacation home rental. It is located in the city center and has a fireplace, a patio, 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 can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Winchester?

Expedia has 9 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Community Park and College Park are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Cassell Creek Golf Course and Winchester Opera House 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.