Photo by Hyelsinta

Winchester Vacation Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jun 26 - Jun 27
Tomorrow
Jun 27 - Jun 28
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Winchester

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Interior

River Relaxation - Calm Riverfront Home in Winchester Kentucky

7.0 out of 10, Good, (4)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Our Little Acorn Tiny House
Property grounds

Our Little Acorn Tiny House

9.4 out of 10, Exceptional, (6)
"I loved our stay at the tiny home! Super communicative owners. Would definitely stay again. "
Our Little Acorn Tiny House
Sylvan Float Treehouse: Our First & Sweetest Treehouse!
Exterior

Sylvan Float Treehouse: Our First & Sweetest Treehouse!

8.8 out of 10, Excellent, (3)
"I feel there should have been a little more disclosure of how primitive this facility really is, starting with the drive getting in to it. If I had of driven any of my other vehicles, I'm not sure I would have been able to get to it. Having a flashlight with some batteries was not mentioned anywhere and using a battery powered fan for circulation was a little rough. I didnt remember reading about a composting toilet, but maybe the excitement of staying in a treehouse distracted me a little....
Sylvan Float Treehouse: Our First & Sweetest Treehouse!
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Fridge, microwave, stovetop, dishwasher

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

10.0 out of 10, Exceptional, (2)
"This was the perfect little cabin for our anniversary getaway. Had everything we needed for cooking at the cabin on the days we didn't want to venture out to eat. Houae was super clean and exactly like the listing! Would definitely stay again if we revisit the area."
The price is ￥13,358
￥37,466 total
includes taxes & fees
Jun 29 - Jun 30
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Fridge, microwave, stovetop, dishwasher

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg

9.0 out of 10, Wonderful, (2)
"Very clean cabin, in perfect condition. Had a hard time finding it in the dark, I would suggest ariving in the daylight it is in the woods with many cabins on the same road so it can be a little confusing to find at night. Everything worked properly and we had a great time!"
The price is ￥13,358
￥37,143 total
includes taxes & fees
Jul 1 - Jul 2
Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
Candlelight Cabin Red River Gorge
Outdoor spa tub

Candlelight Cabin Red River Gorge

10.0 out of 10, Exceptional, (20)
"Wonderfully cozy."
The price is ￥24,684
￥43,165 total
includes taxes & fees
Jul 7 - Jul 8
Candlelight Cabin Red River Gorge
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!
Exterior

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

9.4 out of 10, Exceptional, (19)
"Great house to come home to after a day of hiking! The location allowed us the opportunity to enjoy the local restaurants "
The price is ￥19,839
￥37,022 total
includes taxes & fees
Jul 10 - Jul 11
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!
New Barndo/ATV Parking/Private Access to Red River
Private kitchen

New Barndo/ATV Parking/Private Access to Red River

10.0 out of 10, Exceptional, (3)
"We stayed here for one night and wish we could have stayed longer. The property was incredible. Very thoughtfully decorated, spacious, and has everything you need plus more. Highly recommend!"
The price is ￥40,929
￥77,135 total
includes taxes & fees
Jul 10 - Jul 11
New Barndo/ATV Parking/Private Access to Red River
New Barndo/Private Access Red River/Kayak/Fishing
Private kitchen

New Barndo/Private Access Red River/Kayak/Fishing

10.0 out of 10, Exceptional, (7)
"Everything was very clean upon arrival and we had no issues getting in upon arrival. We would stay again without a doubt!"
The price is ￥29,638
￥61,165 total
includes taxes & fees
Jul 15 - Jul 16
New Barndo/Private Access Red River/Kayak/Fishing
New Barndo/Private Red River Access/Kayak Launch
Private kitchen

New Barndo/Private Red River Access/Kayak Launch

10.0 out of 10, Exceptional, (5)
"Perfect and relaxing"
The price is ￥30,893
￥64,629 total
includes taxes & fees
Jul 15 - Jul 16
New Barndo/Private Red River Access/Kayak Launch
New Barndo/ATV Trailer Park/Outdoor Shower/HotTub
Private kitchen

New Barndo/ATV Trailer Park/Outdoor Shower/HotTub

9.8 out of 10, Exceptional, (9)
"After a long day of hiking, the hot tub felt amazing! Very spacious and beautifully decorated! Highly recommend!!"
The price is ￥31,363
￥63,387 total
includes taxes & fees
Jul 15 - Jul 16
New Barndo/ATV Trailer Park/Outdoor Shower/HotTub
New Barndo/Kayak Launch/ 2 Private Hot Tubs
Private kitchen

New Barndo/Kayak Launch/ 2 Private Hot Tubs

10.0 out of 10, Exceptional, (6)
"We were a group of 12 and we had a great stay. Daniel was very attentive to us before and during our stay. We had both sides of the barn and it was perfect. Great location. Clean. We would love to be able to stay again"
The price is ￥87,817
￥165,479 total
includes taxes & fees
Jul 15 - Jul 16
New Barndo/Kayak Launch/ 2 Private Hot Tubs
New Barndo/Kayak Launch/ 2 Private Hot Tubs
Private kitchen

New Barndo/Kayak Launch/ 2 Private Hot Tubs

10.0 out of 10, Exceptional, (6)
"This place was perfect! So picturesque and peaceful. Great location, amenities and the owners were wonderful. Highly recommend and will definitely be back!"
The price is ￥89,699
￥167,873 total
includes taxes & fees
Jul 6 - Jul 7
New Barndo/Kayak Launch/ 2 Private Hot Tubs
Pool - Fire Pit - RV Parking - Family Friendly
Private kitchen

Pool - Fire Pit - RV Parking - Family Friendly

The price is ￥43,560
￥109,808 total
includes taxes & fees
Jul 13 - Jul 14
Pool - Fire Pit - RV Parking - Family Friendly
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
Fridge, microwave, oven, stovetop

Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!

10.0 out of 10, Exceptional, (11)
"Biggie cabin was perfect, and great location! Would absolutely stay there again! "
The price is ￥34,993
￥71,414 total
includes taxes & fees
Jul 15 - Jul 16
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
This house is a 5 bedroom(s), 3.5 bathrooms, located in Stanton, KY.
Fridge, microwave, oven, stovetop

This house is a 5 bedroom(s), 3.5 bathrooms, located in Stanton, KY.

9.2 out of 10, Wonderful, (5)
"Lovely home, spacious, with lots of extras. The curvy road was a bit of a challenge in the dark. Owner probably should find another cleaning service, as the downstairs & steps had not been vacuumed"
The price is ￥83,054
￥138,082 total
includes taxes & fees
Jul 20 - Jul 21
This house is a 5 bedroom(s), 3.5 bathrooms, located in Stanton, KY.
"Hickory Heights" - Overlook Dome 006 in RRG
1 bedroom, iron/ironing board, WiFi, bed sheets

"Hickory Heights" - Overlook Dome 006 in RRG

10.0 out of 10, Exceptional, (2)
"Such a fun and unique property! It was great for a birthday/date getaway weekend!! "
The price is ￥26,717
￥48,340 total
includes taxes & fees
Jul 10 - Jul 11
"Hickory Heights" - Overlook Dome 006 in RRG
Red RIver Gorge, Hollerwood, High Speed Wi-Fi, KY Dragway
Interior

Red RIver Gorge, Hollerwood, High Speed Wi-Fi, KY Dragway

10.0 out of 10, Exceptional, (1)
"great place! will be back!"
The price is ￥29,040
￥41,138 total
includes taxes & fees
Jun 29 - Jun 30
Red RIver Gorge, Hollerwood, High Speed Wi-Fi, KY Dragway
Red River Gorge, High Speed Wi-Fi, KY Dragway, Hollerwood Stay
Microwave, oven, stovetop, dishwasher

Red River Gorge, High Speed Wi-Fi, KY Dragway, Hollerwood Stay

10.0 out of 10, Exceptional, (6)
"Property was very nice. Clean, decor was very cute. Owner was very responsive. Great property."
The price is ￥26,136
￥37,296 total
includes taxes & fees
Jul 2 - Jul 3
Red River Gorge, High Speed Wi-Fi, KY Dragway, Hollerwood Stay
Red River Gorge, Hollerwood Stays! High Speed Wi-Fi, Pet-Friendly! New Home!
Outdoor dining

Red River Gorge, Hollerwood Stays! High Speed Wi-Fi, Pet-Friendly! New Home!

9.8 out of 10, Exceptional, (7)
"Very clean, cute house."
The price is ￥24,829
￥36,815 total
includes taxes & fees
Jun 29 - Jun 30
Red River Gorge, Hollerwood Stays! High Speed Wi-Fi, Pet-Friendly! New Home!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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?

ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail: Visitors like this Winchester vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Winchester?

Expedia has 8 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Lykins Park and College Park are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Southwind 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.