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 Holiday Rentals

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Our top choices for Winchester holiday rentals

1. 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 NZ$517
includes taxes & fees
21 Aug - 22 Aug
The Winchester

2. 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.
The price is NZ$495
includes taxes & fees
30 Aug - 31 Aug
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

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 NZ$670
includes taxes & fees
26 Aug - 27 Aug
River Relaxation - Calm Riverfront Home in Winchester Kentucky

4. 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 traveller
The price is NZ$319
includes taxes & fees
27 Aug - 28 Aug
Unique Stay in a 1907 Log Cabin on The Kentucky River

5. 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, (75 reviews)
"It was really great staying in a historical home. It was clean and very comfortable."
United States
Nancy L.
The price is NZ$401
includes taxes & fees
7 Sept - 8 Sept
1800’s Historical Log Cabin near I-75 Interstate

6. 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 NZ$210
includes taxes & fees
23 Aug - 24 Aug
Cozy, Bright Home in Historic Downtown

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

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (54 reviews)
"We thoroughly enjoyed our stay! Dalton was easy to communicate with, gave clear guidance for check-in and check-out procedures, and offered a lovely home to relax in. If back in the area we would absolutely stay here again!"
United States
Tara G.
The price is NZ$419
includes taxes & fees
24 Aug - 25 Aug
Relaxing Hot Tub | S’mores Fire Pit | Garage

8. 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, (122 reviews)
"great place!"
United States
Ava G.
The price is NZ$322
includes taxes & fees
23 Aug - 24 Aug
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

9. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (14 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 NZ$338
includes taxes & fees
24 Aug - 25 Aug
Cozy 1-bedroom in Lexington

10. Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (54 reviews)
"Clean, well stocked and comfortable. I always enjoy my stay here. "
United States
Robert T.
The price is NZ$342
includes taxes & fees
20 Sept - 21 Sept
Luxury on Main / South

11. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (347 reviews)
"Felt very comfortable during our stay,plenty of space for us both."
United States
Anonymous traveller
The price is NZ$113
includes taxes & fees
23 Aug - 24 Aug
2 Full Beds | Non-Smoking, Micfridge

12. Midnight Lexington Newly Remodeled Designer Stay

Midnight Lexington Newly Remodeled Designer Stay
Lexington
9.8 out of 10, Exceptional, (41 reviews)
The price is NZ$756
includes taxes & fees
2 Sept - 3 Sept
Midnight Lexington Newly Remodeled Designer Stay

13. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (92 reviews)
"Such a wonderful little hidden gem! The host was fantastic and was perfect for a trip up to Lexington! Would use again and would highly recommend!"
United States
Matthew Y.
The price is NZ$283
includes taxes & fees
23 Aug - 24 Aug
Treetops Solar Sanctuary

14. 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, (8 reviews)
"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"
United States
Jessica
The price is NZ$286
includes taxes & fees
25 Aug - 26 Aug
Dappled Grey Cabin with hot tub at Red River Gorge

15. 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, (90 reviews)
"Everything was fantastic!!"
United States
Leah Anne G.
The price is NZ$376
includes taxes & fees
26 Aug - 27 Aug
Modern 2bd 2ba - Near I75, No Steps, Free Wifi

16. My Old Kentucky Home

My Old Kentucky Home
Lexington
9.8 out of 10, Exceptional, (32 reviews)
"Great place for a nice weekend visit."
United States
brian g.
The price is NZ$411
includes taxes & fees
15 Sept - 16 Sept
My Old Kentucky Home

17. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,005 reviews)
"Friendly staff and good view."
United States
LE VAN
The price is NZ$177
includes taxes & fees
16 Sept - 17 Sept
Natural Bridge State Resort Park

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

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (51 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is NZ$396
includes taxes & fees
23 Aug - 24 Aug
Conveniently Located ~ WiFi ~ Central Heat & Air.

19. Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (41 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is NZ$292
includes taxes & fees
23 Aug - 24 Aug
Mountaintop Cottage

20. 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, (15 reviews)
"The condo was beautiful and very clean and everything we needed from dishes and kitchen items to laundry, facilities, and soap and accessories. We enjoyed this place and will happily stay again."
United States
Sylvia B.
The price is NZ$291
includes taxes & fees
31 Aug - 1 Sept
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
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

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as NZ$113 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffee shops and shopping during your trip.

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

Renovated train station on thoroughbred horse farm.: This holiday home rental outside of Winchester is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Winchester?

Expedia has 8 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

Wiseman Park and College 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.