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Our top choices for Winchester holiday rentals

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 £227
includes taxes & fees
10 May - 11 May
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

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, (37 reviews)
"Everything was perfect! Would definitely stay again "
United States
stacie s.
The price is £100
includes taxes & fees
11 May - 12 May
Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4

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 £140
includes taxes & fees
10 May - 11 May
Conveniently Located ~ WiFi ~ Central Heat & Air.

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
9.8 out of 10, Exceptional, (17 reviews)
"Everything was a advertised, this was our second stay here and would come back. "
United States
Chris F.
The price is £100
includes taxes & fees
10 May - 11 May
Furnished Glamping Tent/2 Queen Beds/Red River Access- Soaring Eagle - #7

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,871 reviews)
"Great location, great hot breakfast "
United States
Nancy
The price is £88
includes taxes & fees
17 May - 18 May
Natural Bridge State Resort Park

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, (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 £143
includes taxes & fees
12 May - 13 May
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Muddy Boots Hideout l Cozy 2BR l 15 min to RRG l WI-FI

Muddy Boots Hideout l Cozy 2BR l 15 min to RRG l WI-FI
Stanton
9.4 out of 10, Exceptional, (17 reviews)
"It's a great place, I love Red River Gorge, and Bruen's restaurant"
United States
david
The price is £130
includes taxes & fees
10 May - 11 May
Muddy Boots Hideout l Cozy 2BR l 15 min to RRG l WI-FI

"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 £166
includes taxes & fees
11 May - 12 May
"Rocky Top" - Cozy RRG Cabin

Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion

Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion
Irvine
9.8 out of 10, Exceptional, (15 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 £158
includes taxes & fees
10 May - 11 May
Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion

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 £111
includes taxes & fees
10 May - 11 May
Unique, Cozy Stay near Red River Gorge

The Lazy Hiker l Cozy 2BR l 15 min to RRG l WI-FI

The Lazy Hiker l Cozy 2BR l 15 min to RRG l WI-FI
Stanton
9.8 out of 10, Exceptional, (16 reviews)
"It was convenient to the Jorge and other activities "
United States
Robin
The price is £127
includes taxes & fees
10 May - 11 May
The Lazy Hiker l Cozy 2BR l 15 min to RRG l WI-FI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (45 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 £157
includes taxes & fees
10 May - 11 May
Briar Patch Cabin RRG: Firepit, Sunset, WIFI

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
Dappled Grey Cabin with hot tub at Red River Gorge

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (5 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 £186
includes taxes & fees
11 May - 12 May
"Cardinal Crest" - Overlook Dome 002 in RRG

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
9.2 out of 10, Wonderful, (5 reviews)
"Great "off the beaten path" cabin with nice touches and good amenities, quick wifi , great hot tub. Gotta love that wrap around porch/ decking, you're definitely in nature there. Would do it again but next time I'd get there with the 4x4 not the sport coupe, lol!"
United States
Daniel
Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge

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 £200
includes taxes & fees
10 May - 11 May
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

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 £157
includes taxes & fees
10 May - 11 May
Mountain Memories Cabin

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (127 reviews)
"Wonderful stay! Everything was clean and view was great. Thanks for a great stay! "
United States
Abby H.
The price is £210
includes taxes & fees
13 May - 14 May
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Georgetown
8.6 out of 10, Excellent, (33 reviews)
"We had a beautiful stay. This house has a wonderful home feel! It was clean and had everything we needed. We will be back! "
United States
Corrie S.
The price is £134
includes taxes & fees
10 May - 11 May
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

Just 1 mile from Natural Bridge State Park!

Just 1 mile from Natural Bridge State Park!
Slade
8.8 out of 10, Excellent, (29 reviews)
"The house was very welcoming and the cabin was beautiful"
United States
Sherry Z.
Just 1 mile from Natural Bridge State Park!
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

Everything you need to know about Winchester holiday rentals

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

Winchester holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as £88 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 holiday 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 holiday.

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 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.