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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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
9.4 out of 10, Exceptional, (13 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is SAR 507
SAR 1,055 total
includes taxes & fees
29 Sep - 30 Sep
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
The price is SAR 507
SAR 1,055 total
includes taxes & fees
29 Sep - 30 Sep
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.
The price is SAR 408
SAR 1,269 total
includes taxes & fees
29 Sep - 30 Sep
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Smart TV, fireplace, books

4. 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, (80 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
The price is SAR 488
SAR 915 total
includes taxes & fees
29 Sep - 30 Sep
1800’s Historical Log Cabin near I-75 Interstate
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

5. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,069 reviews)
"Great place to stay."
United States
Monty
The price is SAR 423
SAR 467 total
includes taxes & fees
18 Oct - 19 Oct
Natural Bridge State Resort Park
Smart TV, fireplace, books

6. 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, (114 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
The price is SAR 387
SAR 710 total
includes taxes & fees
29 Sep - 30 Sep
Unique Stay in a 1907 Log Cabin on The Kentucky River
Property grounds

7. Midnight Lexington Newly Remodeled Designer Stay

Midnight Lexington Newly Remodeled Designer Stay
Lexington
9.8 out of 10, Exceptional, (41 reviews)
"Everything was great, the house was clean and well appointed. We had everything we needed. It was super comfortable and had a cool interior design. The location was quiet and convenient. We felt like we were close to everything from shopping to downtown. We look forward to our next stay."
United States
Michael M.
Midnight Lexington Newly Remodeled Designer Stay
Terrace/patio

8. Relaxing Hot Tub | S’mores Fire Pit | Garage

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (55 reviews)
"Stay was fine. Location is good."
United States
Lori M.
The price is SAR 814
SAR 1,528 total
includes taxes & fees
7 Oct - 8 Oct
Relaxing Hot Tub | S’mores Fire Pit | Garage
Exterior detail

9. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
The price is SAR 1,220
SAR 1,716 total
includes taxes & fees
5 Oct - 6 Oct
Cabin in Kentucky Horse Country
Coffee/tea maker, fridge, microwave, oven

10. Entire Home in Hamburg!

Entire Home in Hamburg!
Liberty Area
10.0 out of 10, Exceptional, (37 reviews)
"Very nice place. "
United States
Monte R.
Entire Home in Hamburg!
Dining

11. 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.
The price is SAR 357
SAR 683 total
includes taxes & fees
29 Sep - 30 Sep
Luxury on Main / South
Exterior

12. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (17 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
The price is SAR 270
SAR 837 total
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-bedroom in Lexington
Coffee/tea maker, fridge, microwave, oven

13. This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.

This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Castlewood
9.4 out of 10, Exceptional, (97 reviews)
"Great property for our family. "
United States
Jake C.
The price is SAR 563
SAR 1,331 total
includes taxes & fees
29 Sep - 30 Sep
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Exterior detail

14. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (92 reviews)
"Great place to stay!"
United States
Anna C.
The price is SAR 297
SAR 668 total
includes taxes & fees
29 Sep - 30 Sep
Treetops Solar Sanctuary
Property grounds

15. 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.
The price is SAR 237
SAR 468 total
includes taxes & fees
29 Sep - 30 Sep
Cozy, Bright Home in Historic Downtown
Smart TV

16. My Old Kentucky Home

My Old Kentucky Home
Lexington
9.8 out of 10, Exceptional, (34 reviews)
"Great place for a nice weekend visit."
United States
brian g.
The price is SAR 357
SAR 1,002 total
includes taxes & fees
29 Sep - 30 Sep
My Old Kentucky Home
Property grounds

17. Spacious Secluded Cabin on 100 Acres Near Red River Gorge

Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Irvine
9.8 out of 10, Exceptional, (96 reviews)
"The property was very clean and nice for our stay. The only complaint was that the main cabin was pretty hot and the wall unit was not able to cool the living room/main living space down. It doesn’t help that it has been 90 degrees though, so I’m sure this place is 5 stars during the fall!"
United States
Kamryn
The price is SAR 405
SAR 944 total
includes taxes & fees
29 Sep - 30 Sep
Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Dining

18. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (349 reviews)
"It felt like home during our stay! Friendly staff made us feel welcome."
United States
Anonymous traveler
The price is SAR 231
SAR 254 total
includes taxes & fees
4 Oct - 5 Oct
2 Full Beds | Non-Smoking, Micfridge
Microwave, oven, stovetop

19. 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.
The price is SAR 245
SAR 720 total
includes taxes & fees
29 Sep - 30 Sep
Modern Studio - Stylish Apartment in Downtown Lexington
Exterior

20. 💙Modern Downtown with Parking - Keeneland - Horse Park

💙Modern Downtown with Parking - Keeneland - Horse Park
Lexington
9.8 out of 10, Exceptional, (44 reviews)
"Great stay"
United States
chris O.
The price is SAR 561
SAR 1,363 total
includes taxes & fees
29 Sep - 30 Sep
💙Modern Downtown with Parking - Keeneland - Horse Park
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

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent
"Great stay- clean and homey! Would def go back!"
Marcy 2-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Georgetown, KY

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?

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. 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.