Winchester Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Winchester vacation 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.
$281 nightly
The price is $309
May 10 - May 11
Total with taxes and fees
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Exterior

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.
$119 nightly
The price is $132
May 10 - May 11
Total with taxes and fees
Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4
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.
$155 nightly
The price is $176
May 10 - May 11
Total with taxes and fees
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
9.8 out of 10, Exceptional, (17 reviews)
"Everything was a advertised, this was our second stay here and would come back. "
United States
Chris F.
$119 nightly
The price is $132
May 10 - May 11
Total with taxes and fees
Furnished Glamping Tent/2 Queen Beds/Red River Access- Soaring Eagle - #7
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,870 reviews)
"Great location, great hot breakfast "
United States
Nancy
$121 nightly
The price is $133
May 10 - May 11
Total with taxes and fees
Natural Bridge State Resort Park
Property grounds

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.
$174 nightly
The price is $192
May 10 - May 11
Total with taxes and fees
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Interior

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
$142 nightly
The price is $161
May 10 - May 11
Total with taxes and fees
Muddy Boots Hideout l Cozy 2BR l 15 min to RRG l WI-FI
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.
$203 nightly
The price is $223
May 11 - May 12
Total with taxes and fees
"Rocky Top" - Cozy RRG Cabin
Exterior

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.
$193 nightly
The price is $213
May 10 - May 11
Total with taxes and fees
Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion
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.
$133 nightly
The price is $146
May 8 - May 9
Total with taxes and fees
Unique, Cozy Stay near Red River Gorge
Fridge, microwave, oven, stovetop

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
$147 nightly
The price is $166
May 10 - May 11
Total with taxes and fees
The Lazy Hiker l Cozy 2BR l 15 min to RRG l WI-FI
Terrace/patio

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (44 reviews)
"The cabin was very clean and absolutely beautiful! Check in was a breeze and host was very kind."
United States
Stacy B.
$192 nightly
The price is $212
May 10 - May 11
Total with taxes and fees
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
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
$217 nightly
The price is $224
May 11 - May 12
Total with taxes and fees
Dappled Grey Cabin with hot tub at Red River Gorge
1 bedroom, iron/ironing board, travel crib, WiFi

"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.
$218 nightly
The price is $240
May 10 - May 11
Total with taxes and fees
"Cardinal Crest" - Overlook Dome 002 in RRG
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
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
$227 nightly
The price is $250
May 31 - Jun 1
Total with taxes and fees
Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge
House (1 Bedroom) | 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 traveler
$247 nightly
The price is $272
May 10 - May 11
Total with taxes and fees
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
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
$192 nightly
The price is $212
May 10 - May 11
Total with taxes and fees
Mountain Memories Cabin
Terrace/patio

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.
$259 nightly
The price is $285
May 10 - May 11
Total with taxes and fees
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Property grounds

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.
$175 nightly
The price is $177
May 10 - May 11
Total with taxes and fees
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Outdoor spa tub

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

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

8/10 Good
"Pool, hot tub and breakfast were excellent. Room comfort was very good, too. The hallway carpet smelled a little musty but we were very happy overall with our stay. Staff was very kind and helpful, and the lobby cookies were a nice touch!"
Karen and Steven 1-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, Georgetown, KY

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

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

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $132 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Hot Tub! Fire pit! Picnic area & Grill! View Hardwicks Creek Haven@RRG: Visitors like this Winchester vacation home rental. It is located in a rural location and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Winchester?

Expedia has 6 vacation 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 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.