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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Check prices for these dates

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

Our top choices for Winchester holiday 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.
The price is HK$1,059
HK$2,205 total
includes taxes & fees
19 Sept - 20 Sept
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 HK$1,059
HK$2,291 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$1,639
HK$3,795 total
includes taxes & fees
18 Sept - 19 Sept
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Exterior

4. 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.
The price is HK$465
HK$1,031 total
includes taxes & fees
16 Sept - 17 Sept
Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3
Coffee/tea maker, fridge, microwave, oven

5. 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.
The price is HK$714
HK$1,770 total
includes taxes & fees
16 Sept - 17 Sept
Conveniently Located ~ WiFi ~ Central Heat & Air.
Living area

6. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,051 reviews)
"Great place to stay."
United States
Monty
The price is HK$783
HK$863 total
includes taxes & fees
20 Sept - 21 Sept
Natural Bridge State Resort Park
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 traveller
The price is HK$481
HK$529 total
includes taxes & fees
20 Sept - 21 Sept
2 Full Beds | Non-Smoking, Micfridge
Property grounds

8. 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.
Cozy, Bright Home in Historic Downtown
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
The price is HK$565
HK$1,766 total
includes taxes & fees
21 Sept - 22 Sept
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, (125 reviews)
"The cabin was clean and just what we needed for our weekend trip."
United States
Emmalynn P.
The price is HK$692
HK$1,506 total
includes taxes & fees
16 Sept - 17 Sept
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
1 bedroom, iron/ironing board, WiFi, bed sheets

11. Westfield Blue

Westfield Blue
Richmond
9.4 out of 10, Exceptional, (11 reviews)
"This is a fantastic property. Incredible comfort, walkable to all of the historic downtown, and delightfully and tastefully decorated. I even took ideas for a home I am designing."
United States
Keith G.
The price is HK$692
HK$1,368 total
includes taxes & fees
21 Sept - 22 Sept
Westfield Blue
Smart TV, fireplace, books

12. 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 HK$808
HK$1,484 total
includes taxes & fees
17 Sept - 18 Sept
Unique Stay in a 1907 Log Cabin on The Kentucky River
Living area

13. 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.
The price is HK$534
HK$1,928 total
includes taxes & fees
16 Sept - 17 Sept
3 Miles Hollerwood/ATV Parking/Mountain Views
Property grounds

14. 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 traveller
Larkspur Cabin with Hot Tub near Red River Gorge
Outdoor dining

15. 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
9.8 out of 10, Exceptional, (40 reviews)
"Great spot, great location, great host."
United States
Jill
The price is HK$820
HK$1,224 total
includes taxes & fees
21 Sept - 22 Sept
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Dining

16. 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 HK$894
HK$1,600 total
includes taxes & fees
22 Sept - 23 Sept
Luxury on Main / South
TV

17. 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.
The price is HK$784
HK$1,382 total
includes taxes & fees
16 Sept - 17 Sept
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Property grounds

18. Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.4 out of 10, Very good, (41 reviews)
"Beautiful little cabin"
United States
Ryan W.
Quaint, heavily forested cabin, mountain valley view.
Property grounds

19. Red River Gorge Cozy Glamping Tent for 4 • AC, Fire Pit & Hot Tub

Red River Gorge Cozy Glamping Tent for 4 • AC, Fire Pit & Hot Tub
Stanton
10.0 out of 10, Exceptional, (7 reviews)
"Yes, I brought my tiny dog and she loved it there as much as we did! "
United States
Kimberly J.
The price is HK$941
HK$1,844 total
includes taxes & fees
21 Sept - 22 Sept
Red River Gorge Cozy Glamping Tent for 4 • AC, Fire Pit & Hot Tub
Smart TV, fireplace, books

20. 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
The price is HK$1,020
HK$1,911 total
includes taxes & fees
21 Sept - 22 Sept
1800’s Historical Log Cabin near I-75 Interstate
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

Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington I-75 Hamburg

10/10 Excellent
"It was a nice overnight stop"
Shelley 1-night trip
Posted 4 hours ago
Motel 6 Lexington I-75 Hamburg

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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?

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 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.