Winchester Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

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$1,164
HK$2,423 total
includes taxes & fees
27 Apr - 28 Apr
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$1,058
HK$2,289 total
includes taxes & fees
7 May - 8 May
The Winchester
Exterior

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.0 out of 10, Good, (4 reviews)
"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! "
United States
Maeve R.
The price is HK$901
HK$2,859 total
includes taxes & fees
27 Apr - 28 Apr
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Property grounds

Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6

Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6
Stanton
9.8 out of 10, Exceptional, (28 reviews)
"It’s cozy and located in a beautiful area. "
United States
Danny P.
The price is HK$490
HK$1,232 total
includes taxes & fees
27 Apr - 28 Apr
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6
Fridge, microwave, oven, stovetop

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (49 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is HK$697
HK$1,457 total
includes taxes & fees
3 May - 4 May
Conveniently Located ~ WiFi ~ Central Heat & Air.
Property grounds

Furnished Glamping Tent/2 Queen Beds/Red River Access- Soaring Eagle - #7

Furnished Glamping Tent/2 Queen Beds/Red River Access- Soaring Eagle - #7
Stanton
9.6 out of 10, Exceptional, (15 reviews)
"Everything was a advertised, this was our second stay here and would come back. "
United States
Chris F.
The price is HK$465
HK$1,030 total
includes taxes & fees
27 Apr - 28 Apr
Furnished Glamping Tent/2 Queen Beds/Red River Access- Soaring Eagle - #7
Living area

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,863 reviews)
"Great location, great hot breakfast "
United States
Nancy
The price is HK$818
HK$901 total
includes taxes & fees
3 May - 4 May
Natural Bridge State Resort Park
Interior

"Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.2 out of 10, Wonderful, (14 reviews)
"Great location "
United States
Zach M.
The price is HK$694
HK$1,586 total
includes taxes & fees
28 Apr - 29 Apr
"Rocky Top" - Cozy RRG Cabin
Private kitchen

Unique, Cozy Stay near Red River Gorge

Unique, Cozy Stay near Red River Gorge
Slade
7.4 out of 10, Good, (10 reviews)
"Great for a quick one nite stay!!"
United States
Khanrad W.
The price is HK$609
HK$1,141 total
includes taxes & fees
27 Apr - 28 Apr
Unique, Cozy Stay near Red River Gorge
Terrace/patio

THIS IS THE ONE!-COUPLE’S CABIN-HOT TUB-MOBILE BOOKING DISCOUNT-CLEAN-GREAT VIEW

THIS IS THE ONE!-COUPLE’S CABIN-HOT TUB-MOBILE BOOKING DISCOUNT-CLEAN-GREAT VIEW
Stanton
10.0 out of 10, Exceptional, (126 reviews)
"Wonderful stay! Everything was clean and view was great. Thanks for a great stay! "
United States
Abby H.
The price is HK$1,258
HK$2,190 total
includes taxes & fees
27 Apr - 28 Apr
THIS IS THE ONE!-COUPLE’S CABIN-HOT TUB-MOBILE BOOKING DISCOUNT-CLEAN-GREAT VIEW
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$768
HK$2,151 total
includes taxes & fees
27 Apr - 28 Apr
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Exterior

240 Sq Ft Tiny Home w/ WIFI in Irvine

240 Sq Ft Tiny Home w/ WIFI in Irvine
Irvine
10.0 out of 10, Exceptional, (14 reviews)
"Perfect little get away for our anniversary! We had a great time exploring Red River Gorge and it was nice having a place like this to come back to. We cooked breakfast every morning on the griddle and the tutorial video for the pellet stove was much appreciated!"
United States
Jacob S.
The price is HK$744
HK$1,658 total
includes taxes & fees
27 Apr - 28 Apr
240 Sq Ft Tiny Home w/ WIFI in Irvine
Outdoor spa tub

Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge

Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge
Stanton
10.0 out of 10, Exceptional, (3 reviews)
"Great cabin, awesome hot tub. Amazing experience"
United States
Brian E.
The price is HK$776
HK$1,805 total
includes taxes & fees
27 Apr - 28 Apr
Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge
Property grounds

Hot Tub! Tiny House Retreat in the Woods

Hot Tub! Tiny House Retreat in the Woods
Stanton
7.8 out of 10, Good, (10 reviews)
"Amazing little place in the heart of RRG"
United States
Madelyn B.
The price is HK$658
HK$1,417 total
includes taxes & fees
27 Apr - 28 Apr
Hot Tub! Tiny House Retreat in the Woods
Terrace/patio

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (72 reviews)
"We loved our stay. If you want a quiet out of the way get-a-way, this it it! The cabin was very clean and had what we needed. We had the pleasure of meeting the host in person when he brought us fire wood and he was very nice. We enjoyed feeding the donkeys and meeting the neighboring dogs who were super friendly. We would definitely stay here again."
United States
Lisa
The price is HK$1,097
HK$1,555 total
includes taxes & fees
27 Apr - 28 Apr
Mountain Memories Cabin
Terrace/patio

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (33 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$1,019
HK$1,468 total
includes taxes & fees
27 Apr - 28 Apr
Mountaintop Cottage
Interior

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Stanton
10.0 out of 10, Exceptional, (319 reviews)
"Great place will be returning "
United States
mel k.
The price is HK$1,258
HK$2,268 total
includes taxes & fees
28 Apr - 29 Apr
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
1 bedroom, iron/ironing board, WiFi, bed sheets

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (4 reviews)
"Very quiet, cozy and a nice place to come back to after a long day of physical activity! "
United States
Gregory L.
The price is HK$1,009
HK$2,028 total
includes taxes & fees
29 Apr - 30 Apr
"Cardinal Crest" - Overlook Dome 002 in RRG
Property grounds

Tranquil Getaway in the Woods ~ Sunset Ridge

Tranquil Getaway in the Woods ~ Sunset Ridge
Irvine
10.0 out of 10, Exceptional, (104 reviews)
"We had a wonderful New Years at this cabin - comfy, clean, close to the gorge, would definitely recommend to anyone looking for a getaway!"
United States
Ben H.
The price is HK$691
HK$1,505 total
includes taxes & fees
3 May - 4 May
Tranquil Getaway in the Woods ~ Sunset Ridge
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, (60 reviews)
"Excellent stopover. "
United States
Robert W.
The price is HK$815
HK$1,673 total
includes taxes & fees
28 Apr - 29 Apr
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

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent
"The room was clean, the staff were great, and the bed was comfortable. My wife and I especially LIKED the blackout blinds as we like sleeping in a dark room. We had one minor issue, reported it and it was fixed right away. We will definitely look to stay at this hotel on future trips. An added benefit, Georgetown was a great town to stay in!"
Michael 4-night trip
Posted 5 hours ago
Country Inn & Suites by Radisson, Georgetown, KY

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?

Hot Tub! Fire pit! Picnic area & Grill! View Hardwicks Creek Haven@RRG: This holiday home rental outside of Winchester is located in a rural location, and has a patio, a garden and a BBQ 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. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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?

Winchester Traveling Trail and Lykins Park are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Winchester Opera House and Clark County Courthouse 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.