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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winchester holiday rentals

A two-story house with a porch and a front yard.

1. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
The price is HK$573
HK$3,316 total
includes taxes & fees
4 Nov - 5 Nov
Charming Victorian Apartment | Downtown Winchester
A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

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
9.6 out of 10, Exceptional, (14 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is HK$1,059
HK$2,188 total
includes taxes & fees
2 Nov - 3 Nov
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.

3. 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$2,188 total
includes taxes & fees
2 Nov - 3 Nov
The Winchester
A two-story wooden cabin with a balcony, surrounded by trees.

4. 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$908
HK$2,731 total
includes taxes & fees
2 Nov - 3 Nov
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.

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, (85 reviews)
"Great location and home for our 10 year anniversary"
United States
Christopher S.
The price is HK$1,090
HK$1,985 total
includes taxes & fees
2 Nov - 3 Nov
1800’s Historical Log Cabin near I-75 Interstate
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 HK$839
HK$1,448 total
includes taxes & fees
3 Nov - 4 Nov
Unique Stay in a 1907 Log Cabin on The Kentucky River
A building with a staircase leading to a door marked with the number 218.

7. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (2 reviews)
"This property was very welcoming to our small dog."
United States
Anne D.
The price is HK$777
HK$960 total
includes taxes & fees
2 Nov - 3 Nov
1 Bedroom Bourbon House on the Hill
A Farmers' Market pavilion with a clear roof, a sign indicating it's powered by KJ, and operating hours from June through October.

8. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (25 reviews)
"This is definitely an older home, but it was clean and comfortable and the Dolly memorabilia is amazing!"
United States
Glenda
The price is HK$494
HK$908 total
includes taxes & fees
2 Nov - 3 Nov
Cozy, Bright Home in Historic Downtown
A log cabin interior with a stone fireplace, wooden walls, and a ceiling fan.

9. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,124 reviews)
"Our king size room was very clean, quiet and comfortable. The hotel setting is beautiful and well kept. The staff made us feel at home and the breakfast buffet and dinner options were fantastic. We'd highly recommend this lodge for other travelers."
United States
Michael
The price is HK$571
HK$629 total
includes taxes & fees
29 Nov - 30 Nov
Natural Bridge State Resort Park
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.

10. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
9.8 out of 10, Exceptional, (356 reviews)
"It felt like home during our stay! Friendly staff made us feel welcome."
United States
Anonymous traveller
The price is HK$457
HK$503 total
includes taxes & fees
2 Nov - 3 Nov
2 Full Beds | Non-Smoking, Micfridge
A cozy outdoor seating area with four Adirondack chairs arranged around a fire pit, surrounded by a gravel path and trees.

11. Midnight Lexington Newly Remodeled Designer Stay

Midnight Lexington Newly Remodeled Designer Stay
Lexington
9.8 out of 10, Exceptional, (43 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.
The price is HK$1,236
HK$3,364 total
includes taxes & fees
3 Nov - 4 Nov
Midnight Lexington Newly Remodeled Designer Stay
A hot tub with two people and a bar area with bottles and a lantern.

12. 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)
"Great stay will think of this place if we ever go back to lexington"
United States
Stephanie S.
The price is HK$942
HK$2,271 total
includes taxes & fees
9 Nov - 10 Nov
Relaxing Hot Tub | S’mores Fire Pit | Garage
A gated entrance with a stone wall, a tree, and white hydrangea flowers.

13. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
The price is HK$2,550
HK$3,646 total
includes taxes & fees
5 Nov - 6 Nov
Cabin in Kentucky Horse Country
A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

14. Westfield Blue & Gazebo Luxury & Privacy Getaway

Westfield Blue & Gazebo Luxury & Privacy Getaway
Richmond
9.6 out of 10, Exceptional, (14 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
The price is HK$579
HK$1,174 total
includes taxes & fees
17 Nov - 18 Nov
Westfield Blue & Gazebo Luxury & Privacy Getaway
A wooden structure with a sign that reads 'TREETOPS ON GARDEN.'

15. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (93 reviews)
"Great place to stay!"
United States
Anna C.
The price is HK$621
HK$1,322 total
includes taxes & fees
9 Nov - 10 Nov
Treetops Solar Sanctuary
A cabin with a deck, a fire pit, and string lights in a forest setting.

16. 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, (133 reviews)
"It was a great cozy place for a weekend for me and my sister. It had everything we needed and we especially loved having the window bed! Would definitely consider staying here again."
United States
Anonymous traveller
The price is HK$713
HK$1,469 total
includes taxes & fees
11 Nov - 12 Nov
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
A kitchen with white cabinets, a central island, and a dining area with wooden chairs and a table.

17. The Towner : Sleeps 4 • Near RRG • Walk to Town

The Towner : Sleeps 4 • Near RRG • Walk to Town
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$777
HK$1,673 total
includes taxes & fees
2 Nov - 3 Nov
The Towner : Sleeps 4 • Near RRG • Walk to Town
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

18. Luxury on Main / South & Downtown Hideaway

Luxury on Main / South & Downtown Hideaway
Richmond
10.0 out of 10, Exceptional, (58 reviews)
"Adorable place. Very clean. Great location. Close to many restaurants and shops. Loved it."
United States
Jordan B.
The price is HK$745
HK$1,358 total
includes taxes & fees
5 Nov - 6 Nov
Luxury on Main / South & Downtown Hideaway
A single-story house with a front porch, a small garden, and a clear pathway leading to the entrance.

19. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (20 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$812
HK$2,044 total
includes taxes & fees
2 Nov - 3 Nov
Cozy 1-bedroom in Lexington
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

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Clean and well maintained with adequate towels and blankets"
Heather 1-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Lexington North

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
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  • 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?

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.