Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester vacation 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 CA $105
CA $571 total
includes taxes & fees
Nov 16 - Nov 17
Charming Victorian Apartment | Downtown Winchester
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 CA $191
CA $399 total
includes taxes & fees
Nov 10 - Nov 11
The Winchester
A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

3. 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 CA $191
CA $399 total
includes taxes & fees
Nov 10 - Nov 11
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
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
8.0 out of 10, Very good, (7 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 CA $182
CA $513 total
includes taxes & fees
Nov 12 - Nov 13
River Relaxation - Calm Riverfront Home in Winchester Kentucky
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, (2,136 reviews)
"Love staying here, such easy access to the Gorge and Natural Bridge. Always convenient and easy to deal with. Always a place I keep in mind when I’m staying in the area."
United States
Logan
The price is CA $79
CA $87 total
includes taxes & fees
Dec 6 - Dec 7
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 CA $151
CA $262 total
includes taxes & fees
Nov 10 - Nov 11
Unique Stay in a 1907 Log Cabin on The Kentucky River
A log cabin interior with a sofa, a coffee table, a fireplace, and a staircase leading to another room.

7. 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, (86 reviews)
"Great location and home for our 10 year anniversary"
United States
Christopher S.
The price is CA $196
CA $361 total
includes taxes & fees
Nov 10 - Nov 11
1800’s Historical Log Cabin near I-75 Interstate
A living room with a sofa, a television, a cabinet, and a plant.

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 CA $89
CA $164 total
includes taxes & fees
Nov 11 - Nov 12
Cozy, Bright Home in Historic Downtown
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.

9. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
9.8 out of 10, Exceptional, (357 reviews)
"Very poor looking motel, both inside and out!"
United States
Miguel
The price is CA $82
CA $90 total
includes taxes & fees
Nov 10 - Nov 11
2 Full Beds | Non-Smoking, Micfridge
A wooden deck with two chairs and a small round table, surrounded by lush greenery.

10. 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 CA $112
CA $238 total
includes taxes & fees
Nov 10 - Nov 11
Treetops Solar Sanctuary
A cabin with a deck, a fire pit, and string lights in a forest setting.

11. 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, (134 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 CA $128
CA $263 total
includes taxes & fees
Nov 11 - Nov 12
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.

12. 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 CA $140
CA $301 total
includes taxes & fees
Nov 10 - Nov 11
The Towner : Sleeps 4 • Near RRG • Walk to Town
A hot tub with two people and a bar area with bottles and a lantern.

13. 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 CA $166
CA $428 total
includes taxes & fees
Nov 12 - Nov 13
Relaxing Hot Tub | S’mores Fire Pit | Garage
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

14. 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 CA $134
CA $246 total
includes taxes & fees
Nov 10 - Nov 11
Luxury on Main / South & Downtown Hideaway
A campsite with several tents on stilts over a sandy area near a river, surrounded by trees.

15. Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4

Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4
Stanton
9.8 out of 10, Exceptional, (59 reviews)
"Great stay"
United States
Josh N.
The price is CA $88
CA $178 total
includes taxes & fees
Nov 15 - Nov 16
Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4
A stone pavilion named Hamburg Pavilion with a flagpole, surrounded by landscaped gardens and trees.

16. 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 CA $223
CA $611 total
includes taxes & fees
Nov 16 - Nov 17
Midnight Lexington Newly Remodeled Designer Stay
A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

17. Westfield Blue & Gazebo Luxury & Privacy Getaway

Westfield Blue & Gazebo Luxury & Privacy Getaway
Richmond
9.6 out of 10, Exceptional, (15 reviews)
"Nice and easy lil spot"
United States
ZACHARY W.
The price is CA $104
CA $212 total
includes taxes & fees
Nov 17 - Nov 18
Westfield Blue & Gazebo Luxury & Privacy Getaway
A single-story house with a front porch, a small garden, and a clear pathway leading to the entrance.

18. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.8 out of 10, Exceptional, (22 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 CA $146
CA $371 total
includes taxes & fees
Nov 11 - Nov 12
Cozy 1-bedroom in Lexington
A modern living room with a sofa, armchairs, and a coffee table. There is a kitchen area with a bar and pendant lights.

19. Graffiti Art Haus - Walk to Central Bank Arena

Graffiti Art Haus - Walk to Central Bank Arena
Downtown Lexington
10.0 out of 10, Exceptional, (59 reviews)
"Enjoyed the stay"
United States
Todd S.
The price is CA $114
CA $272 total
includes taxes & fees
Nov 16 - Nov 17
Graffiti Art Haus - Walk to Central Bank Arena
A gated entrance with a stone wall, a tree, and white hydrangea flowers.

20. 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 CA $459
CA $657 total
includes taxes & fees
Nov 10 - Nov 11
Cabin in Kentucky Horse Country
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

A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester

8/10 Good

Good place to stay
Canada
martin
Reviewed April 30, 2025
Holiday Inn Express Lexington East - Winchester by IHG

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

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

Winchester vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $79 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 vacation 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 vacation.

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 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.