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.

Holiday Rentals in Winchester

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester holiday rentals

A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

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 €286
includes taxes & fees
27 Oct - 28 Oct
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 €286
includes taxes & fees
26 Oct - 27 Oct
The Winchester
A two-story wooden cabin with a balcony, surrounded by trees.

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 €315
includes taxes & fees
28 Sept - 29 Sept
River Relaxation - Calm Riverfront Home in Winchester Kentucky
A log cabin interior with a sofa, a coffee table, a fireplace, and a staircase leading to another room.

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 €220
includes taxes & fees
28 Sept - 29 Sept
1800’s Historical Log Cabin near I-75 Interstate
A log cabin interior with a stone fireplace, wooden walls, and a ceiling fan.

5. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,068 reviews)
"Great place to stay."
United States
Monty
The price is €90
includes taxes & fees
30 Sept - 1 Oct
Natural Bridge State Resort Park
A log cabin interior with a wooden desk, leather armchair, and a patterned rug.

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 traveller
The price is €170
includes taxes & fees
29 Sept - 30 Sept
Unique Stay in a 1907 Log Cabin on The Kentucky River
A cozy outdoor seating area with four Adirondack chairs arranged around a fire pit, surrounded by a gravel path and trees.

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
A hot tub with two people and a bar area with bottles and a lantern.

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.
Relaxing Hot Tub | S’mores Fire Pit | Garage
A gated entrance with a stone wall, a tree, and white hydrangea flowers.

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 €430
includes taxes & fees
27 Oct - 28 Oct
Cabin in Kentucky Horse Country
A modern kitchen with dark cabinetry, a stainless steel refrigerator, and a granite countertop.

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!
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

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 €164
includes taxes & fees
28 Sept - 29 Sept
Luxury on Main / South
A single-story house with a front porch, a small garden, and a clear pathway leading to the entrance.

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 €205
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom in Lexington
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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.
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
A wooden structure with a sign that reads 'TREETOPS ON GARDEN.'

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 €160
includes taxes & fees
28 Sept - 29 Sept
Treetops Solar Sanctuary
A Farmers' Market pavilion with a green signboard, white structural elements, and a covered area with yellow bollards.

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 €113
includes taxes & fees
29 Sept - 30 Sept
Cozy, Bright Home in Historic Downtown
A living room with a fireplace, a staircase, and a TV mounted above it.

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 €240
includes taxes & fees
26 Oct - 27 Oct
My Old Kentucky Home
A wooden cabin with a deck, string lights, and a fire pit.

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 €235
includes taxes & fees
28 Sept - 29 Sept
Spacious Secluded Cabin on 100 Acres Near Red River Gorge
A hotel lobby with a flat-screen TV, a coat rack, a table with chairs, and a view of the outside through large glass doors.

18. 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 traveller
The price is €59
includes taxes & fees
4 Oct - 5 Oct
2 Full Beds | Non-Smoking, Micfridge
A modern kitchen with teal cabinets, a black stove, and a black microwave. There is a black and white rug on the floor.

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 €172
includes taxes & fees
29 Sept - 30 Sept
Modern Studio - Stylish Apartment in Downtown Lexington
A white two-story house with a front porch, a small front yard, and a white picket fence.

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 €330
includes taxes & fees
28 Sept - 29 Sept
💙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

Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

8/10 Good
"Place was clean and comfortable."
Dennis 1-night trip
Posted 2 hours ago
Microtel Inn by Wyndham Lexington

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, apart-hotels, 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 €59 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?

Luxe Home Downtown - Sleeps 6. Off-street parking: This holiday home rental outside of Winchester is located in the city centre, 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winchester?

Expedia has 9 holiday 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 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.