Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

The Perch - NEW / Downtown!

The Perch - NEW / Downtown!
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"The place was amazing! Very clean and comfortable. Great Italian restaurant down the street. Delicious dounuts around the corner.We went down to go into Lexington for Bourbon and wine tours. Would have liked to have a folder/ binder with information on what is in the area ( we did explore downtown) and also for information about checking out.We had 4 adults and could have used more towels (had 1 towel for each person) But we did make due.All in all would give this place 5 stars! We will be...
United States
Angela G.
The price is HK$945
HK$1,967 total
includes taxes & fees
9 Mar - 10 Mar
The Perch - NEW / Downtown!

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
10.0 out of 10, Exceptional, (6 reviews)
"Easy check in, Clean and close to everything. "
United States
Vicky R.
The price is HK$1,020
HK$2,262 total
includes taxes & fees
16 Feb - 17 Feb
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$1,020
HK$2,262 total
includes taxes & fees
16 Feb - 17 Feb
The Winchester

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.
River Relaxation - Calm Riverfront Home in Winchester Kentucky

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$586
HK$1,330 total
includes taxes & fees
15 Feb - 16 Feb
Conveniently Located ~ WiFi ~ Central Heat & Air.

Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
Stanton
10.0 out of 10, Exceptional, (24 reviews)
"Loved our stay. Most definitely coming back, had everything you needed for "
United States
cristal l.
The price is HK$494
HK$1,061 total
includes taxes & fees
15 Feb - 16 Feb
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

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$494
HK$1,061 total
includes taxes & fees
15 Feb - 16 Feb
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,801 reviews)
"Great setting and very convenient to everything. "
United States
WILLIAM
Natural Bridge State Resort Park

Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.4 out of 10, Very good, (29 reviews)
"Cabin was good but other cabins are close cabin was very comfortable road to cabin is very steep but doable "
United States
Terry
The price is HK$821
HK$1,591 total
includes taxes & fees
16 Feb - 17 Feb
Quaint, heavily forested cabin, mountain valley view.

Tranquil Getaway in the Woods ~ Sunset Ridge

Tranquil Getaway in the Woods ~ Sunset Ridge
Irvine
10.0 out of 10, Exceptional, (88 reviews)
"Outstanding place to stay. Cozy and just what we hoped for. "
United States
Benjamin Z.
The price is HK$689
HK$1,019 total
includes taxes & fees
15 Feb - 16 Feb
Tranquil Getaway in the Woods ~ Sunset Ridge

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (41 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$1,330
HK$1,638 total
includes taxes & fees
16 Feb - 17 Feb
Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (27 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$1,055
HK$1,508 total
includes taxes & fees
16 Mar - 17 Mar
Mountaintop Cottage

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
Stanton
9.8 out of 10, Exceptional, (16 reviews)
"Overall the cabin was very nice. There were some minor maintenance issues, such as the electric fireplace not working and the remotes for the tv needing batteries, but it was a great cabin. We enjoyed our stay. "
United States
Anonymous traveller
The price is HK$1,196
HK$2,835 total
includes taxes & fees
16 Feb - 17 Feb
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

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)
"Every aspect of this rental was fantastic!"
United States
Elizabeth S.
The price is HK$1,231
HK$2,086 total
includes taxes & fees
18 Feb - 19 Feb
Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.

A Frame of Mind- Firepit, WiFi, Arcade, Pet Friendly

A Frame of Mind- Firepit, WiFi, Arcade, Pet Friendly
Jeffersonville
9.2 out of 10, Wonderful, (69 reviews)
"It was a great place to stay. Close to everything. The house was clean and had everything you need for your stay. Will be back."
United States
Michelle D.
The price is HK$817
HK$1,667 total
includes taxes & fees
17 Feb - 18 Feb
A Frame of Mind- Firepit, WiFi, Arcade, Pet Friendly

ManeStay- Pet Friendly, Hot Tub, Firepit, 10 mins from Natural Bridge

ManeStay- Pet Friendly, Hot Tub, Firepit, 10 mins from Natural Bridge
Stanton
9.2 out of 10, Wonderful, (126 reviews)
"Great value, location and amenities. The hot tub and deck were enjoyable after hiking all day. The host was quick to respond when the door code wasn’t as communicated on arrival. We will stay here again. "
United States
Shayna F.
The price is HK$1,408
HK$2,672 total
includes taxes & fees
24 Feb - 25 Feb
ManeStay- Pet Friendly, Hot Tub, Firepit, 10 mins from Natural Bridge

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$818
HK$1,484 total
includes taxes & fees
16 Feb - 17 Feb
Dappled Grey Cabin with hot tub at Red River Gorge

Secluded & Tranquil Cabin ~ Near Red River Gorge

Secluded & Tranquil Cabin ~ Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (58 reviews)
"Super inviting and felt like home. . ."
United States
Janet B.
The price is HK$844
HK$2,025 total
includes taxes & fees
15 Feb - 16 Feb
Secluded & Tranquil Cabin ~ Near Red River Gorge

Hot Tub! Tiny House Retreat in the Woods

Hot Tub! Tiny House Retreat in the Woods
Stanton
7.8 out of 10, Good, (6 reviews)
"Overall, great stay! The tiny house looked just like the photos and the hot tub was added relaxation. Lots of hiking options in the area that we were able to explore!The only heads up would be that the drive back to the cabin is gravel, bumpy, and mainly uphill…so if you don’t have a vehicle that can handle it, it could be tricky. Our Jeep made it just fine though!"
United States
Jaimie K.
The price is HK$657
HK$1,413 total
includes taxes & fees
16 Feb - 17 Feb
Hot Tub! Tiny House Retreat in the Woods

Mountain Rose- Hot Tub, Pool Table, Firepit, Fireplace

Mountain Rose- Hot Tub, Pool Table, Firepit, Fireplace
Stanton
9.0 out of 10, Wonderful, (66 reviews)
"Clean and cozy. Perfect for our stay !!!"
United States
Julie
The price is HK$1,104
HK$2,314 total
includes taxes & fees
16 Feb - 17 Feb
Mountain Rose- Hot Tub, Pool Table, Firepit, Fireplace
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

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:

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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?

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location: 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.

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. 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.