Winchester Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Winchester holiday rentals

Fridge, microwave, oven, stovetop

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, (7 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is HK$1,288
HK$2,469 total
includes taxes & fees
27 Mar - 28 Mar
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

The Winchester

The Winchester
Winchester
8.4 out of 10, Very good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The price is HK$1,019
HK$2,241 total
includes taxes & fees
10 Mar - 11 Mar
The Winchester
Fridge, microwave, oven, stovetop

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (48 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is HK$585
HK$1,328 total
includes taxes & fees
5 Mar - 6 Mar
Conveniently Located ~ WiFi ~ Central Heat & Air.
Living area

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,812 reviews)
"Great setting and very convenient to everything. "
United States
WILLIAM
Natural Bridge State Resort Park
Interior

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveller
The price is HK$1,147
HK$2,473 total
includes taxes & fees
5 Mar - 6 Mar
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Terrace/patio

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (28 reviews)
"I cannot say enough how CUTE this was we were so happy we found it. Loved the animals and will definitely stay again."
United States
Jessica H.
The price is HK$1,054
HK$1,506 total
includes taxes & fees
5 Mar - 6 Mar
Mountaintop Cottage
Interior

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Georgetown
10.0 out of 10, Exceptional, (60 reviews)
"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "
United States
l v.
The price is HK$927
HK$1,736 total
includes taxes & fees
5 Mar - 6 Mar
East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Terrace/patio

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (64 reviews)
"Great cabin!!"
United States
Amanda S.
The price is HK$1,132
HK$1,592 total
includes taxes & fees
5 Mar - 6 Mar
Mountain Memories Cabin
Interior

ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail

ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
Lexington
10.0 out of 10, Exceptional, (28 reviews)
"Lovely property. "
United States
Jean W.
The price is HK$4,004
HK$8,887 total
includes taxes & fees
6 Mar - 7 Mar
ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail
Terrace/patio

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (42 reviews)
"The cabin was very clean and absolutely beautiful! Check in was a breeze and host was very kind."
United States
Stacy B.
The price is HK$1,328
HK$1,636 total
includes taxes & fees
5 Mar - 6 Mar
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Smart TV, fireplace

Amazing Views! Hot Tub!! Minutes from the Gorge!!!

Amazing Views! Hot Tub!! Minutes from the Gorge!!!
Stanton
9.4 out of 10, Exceptional, (66 reviews)
"This rental was very cozy and inviting! Our favorite part was the porch with a gorgeous view! It was just my husband and I but 6 guests total would have had everything they needed. The patio had plenty of furniture for relaxing and a very nice outdoor dining set. We can see ourselves coming back with family or friends and enjoying the fire ring and gathering area as well. The host was very helpful and friendly. "
United States
Julie B.
Amazing Views! Hot Tub!! Minutes from the Gorge!!!
TV, fireplace

Dappled Grey Cabin with hot tub at Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"
United States
Jessica
The price is HK$907
HK$1,583 total
includes taxes & fees
10 Mar - 11 Mar
Dappled Grey Cabin with hot tub at Red River Gorge
Property grounds

Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.4 out of 10, Very good, (29 reviews)
"My family and I had a great time during our stay. The cabin is very clean. The atmosphere was just what we needed for our Thanksgiving get-away."
United States
Brooke S.
The price is HK$820
HK$1,589 total
includes taxes & fees
5 Mar - 6 Mar
Quaint, heavily forested cabin, mountain valley view.
Interior

Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge

Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge
Stanton
9.4 out of 10, Exceptional, (54 reviews)
"Wonderful cabin! Great communication with the owner. The interior is up to date and well appointed. I would stay there again."
United States
Amanda
The price is HK$1,002
HK$2,223 total
includes taxes & fees
5 Mar - 6 Mar
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge
TV, fireplace

Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.

Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.
Slade
8.0 out of 10, Very good, (26 reviews)
"Awesome Colors of fall, and a great cabin, this is our 2’nd stay at this cabin!!!"
United States
Al B.
Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.
Property grounds

Secluded & Tranquil Cabin ~ Near Red River Gorge

Secluded & Tranquil Cabin ~ Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (59 reviews)
"Super inviting and felt like home. . ."
United States
Janet B.
The price is HK$843
HK$2,022 total
includes taxes & fees
5 Mar - 6 Mar
Secluded & Tranquil Cabin ~ Near Red River Gorge
Smart TV, fireplace, books

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, (59 reviews)
"Excellent stopover. "
United States
Robert W.
The price is HK$937
HK$1,839 total
includes taxes & fees
5 Mar - 6 Mar
1800’s Historical Log Cabin near I-75 Interstate
Exterior detail

Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (80 reviews)
"Beautiful property and great host. Paris is a quaint town but plenty of activities to do. "
United Kingdom
Brandon K.
The price is HK$2,537
HK$3,817 total
includes taxes & fees
5 Mar - 6 Mar
Cabin in Kentucky Horse Country
Dining

STOP SCROLLING!-COUPLE’S CABIN-HOT TUB IN THE WOODS-RED RIVER GORGE-SUPER CLEAN

STOP SCROLLING!-COUPLE’S CABIN-HOT TUB IN THE WOODS-RED RIVER GORGE-SUPER CLEAN
Stanton
10.0 out of 10, Exceptional, (19 reviews)
"Great place to stay. We had an epic time. "
United States
Tracy S.
The price is HK$1,381
HK$2,358 total
includes taxes & fees
20 Mar - 21 Mar
STOP SCROLLING!-COUPLE’S CABIN-HOT TUB IN THE WOODS-RED RIVER GORGE-SUPER CLEAN
Property grounds

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (157 reviews)
"Had a wonderful time. Would definitely stay again "
United States
Melissa P.
The price is HK$1,105
HK$2,035 total
includes taxes & fees
5 Mar - 6 Mar
STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
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

Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

10/10 Excellent
"The stay was perfect! The room was very spacious which helped with our two dogs. Alexis was very polite and friendly when we checked in. The breakfast had many options. We will definitely stay at Hilton properties in the future. "
Marie 1-night trip
Posted 2 days ago
Home2 Suites by Hilton Lexington 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
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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?

2 or 3 Bedroom/Baths House in Andover Convenient to All of Lexington: This holiday home rental outside of Winchester is located on a lake, 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 and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Winchester?

Expedia has 6 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. Southwind 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.