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Winchester Vacation Rentals

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In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Winchester

Natural Bridge State Resort Park
View from room

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1709)
"Beautiful and quiet place to stay."
Natural Bridge State Resort Park
ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower
Outdoor spa tub

ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower

10.0 out of 10, Exceptional, (8)
"This is a great property we used for a long weekend. Quiet and private yet not a long drive to hiking trails and restaurants. Owner is easy to work with and very kind. Appreciate the use of your property."
The price is ￥22,296
￥40,200 total
includes taxes & fees
Sep 28 - Sep 29
ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower
Luxurious Cabin Across From The Red River Gorge, In The Natural Bridge Area
Exterior

Luxurious Cabin Across From The Red River Gorge, In The Natural Bridge Area

9.6 out of 10, Exceptional, (195)
"Convenient location and great stay!"
Luxurious Cabin Across From The Red River Gorge, In The Natural Bridge Area
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
Free WiFi, bed sheets

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

10.0 out of 10, Exceptional, (20)
"Such an amazing get away "
The price is ￥10,447
￥21,361 total
includes taxes & fees
Sep 30 - Oct 1
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!
Smart TV

The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!

10.0 out of 10, Exceptional, (331)
"Location was great for exploring the Red River Gorge. Hot tub was perfect after long days of hiking!"
The price is ￥27,898
￥47,353 total
includes taxes & fees
Oct 12 - Oct 13
The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Exterior detail

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

8.4 out of 10, Very Good, (22)
"This cottage was such a great place to come back to after a long day of hiking and exploring Red River Gorge. Super cute in & outside with a beautiful landscape. We also had visits from a local cat every morning and night and he was so extremely sweet and made the trip all the more better."
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
"Valley View Lodge" - Modern Spacious Stay RRG - Slade
4 bedrooms, travel crib, WiFi, bed sheets

"Valley View Lodge" - Modern Spacious Stay RRG - Slade

9.6 out of 10, Exceptional, (23)
"Great location for visiting Red River Gorge. We happily will stay there again!"
The price is ￥27,835
￥53,817 total
includes taxes & fees
Sep 29 - Sep 30
"Valley View Lodge" - Modern Spacious Stay RRG - Slade
Quaint, heavily forested cabin, mountain valley view.
Terrace/patio

Quaint, heavily forested cabin, mountain valley view.

2.0 star property
7.8 out of 10, Good, (20)
"Everything was great. The hiking and rocks around the property were awesome. "
Quaint, heavily forested cabin, mountain valley view.
Quaint old fashioned cabin, Loft, Grill, Fire Pit!
Living area

Quaint old fashioned cabin, Loft, Grill, Fire Pit!

8.2 out of 10, Very Good, (21)
"We loved the cabin it was clean , cool and was exactly what we were looking for !! Will definitely book again. "
Quaint old fashioned cabin, Loft, Grill, Fire Pit!
CREEKSIDE CABIN
Terrace/patio

CREEKSIDE CABIN

10.0 out of 10, Exceptional, (1)
"Cute and cozy and very clean."
The price is ￥17,935
￥33,605 total
includes taxes & fees
Sep 30 - Oct 1
CREEKSIDE CABIN
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
Fridge, microwave, oven, stovetop

Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!

10.0 out of 10, Exceptional, (13)
"Biggie cabin was perfect, and great location! Would absolutely stay there again! "
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
Scandanavian Cabin-Hot Tub-EV Charger-Fire Pit-Close to All RRG Action
Terrace/patio

Scandanavian Cabin-Hot Tub-EV Charger-Fire Pit-Close to All RRG Action

10.0 out of 10, Exceptional, (3)
"This was the most beautiful cabin we have ever stayed in! Everything was clean and the kitchen is well stocked with essentials. We had the most relaxing last minute getaway. Shane checked on us several times to assure our stay was great. The cabin is very peaceful and the huge windows accentuate the outdoor beauty making you feel part of the forest."
Scandanavian Cabin-Hot Tub-EV Charger-Fire Pit-Close to All RRG Action
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6
1 bedroom

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

9.8 out of 10, Exceptional, (25)
"It was amazing peaceful great view comfortable beds. "
The price is ￥10,362
￥21,188 total
includes taxes & fees
Sep 29 - Sep 30
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6
Relaxing, cozy cabin in the heart of the Red River Gorge!
Outdoor dining

Relaxing, cozy cabin in the heart of the Red River Gorge!

10.0 out of 10, Exceptional, (118)
"We really enjoyed our stay. The evenings were relaxing hanging out on the porch listening to the rain and nature. Very clean and had everything we needed. Nice and close to a lot of trails and natural attractions. "
Relaxing, cozy cabin in the heart of the Red River Gorge!
Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (17)
"The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions."
The price is ￥19,927
￥28,477 total
includes taxes & fees
Oct 19 - Oct 20
Mountaintop Cottage
Tanzanite-- The "GEM" with a Hot Tub & WiFi!!
Exterior

Tanzanite-- The "GEM" with a Hot Tub & WiFi!!

9.8 out of 10, Exceptional, (46)
"Cozy, attractive cottage near to all the natural attractions and hiking. "
Tanzanite-- The "GEM" with a Hot Tub & WiFi!!
Cliffline Twilight*WOW*Hot tub! Pet Friendly!
Exterior

Cliffline Twilight*WOW*Hot tub! Pet Friendly!

10.0 out of 10, Exceptional, (23)
"New small but nice cabin located near the Nada Tunnel, close to Natural Bridge and DBNF. The cabin is small, featuring a fantastic hot tub and a fire pit set on the ridge above."
Cliffline Twilight*WOW*Hot tub! Pet Friendly!
The WOODS Shipping Container Cabin-High Speed WiFi!-Hot Tub!-Covered Deck!-RELAX
Exterior

The WOODS Shipping Container Cabin-High Speed WiFi!-Hot Tub!-Covered Deck!-RELAX

10.0 out of 10, Exceptional, (296)
"A great little weekend getaway and love the property location. Secluded and private with very little noise from passing vehicles. Also a short drive to Daniele Boone National Park and local shops"
The price is ￥26,422
￥45,563 total
includes taxes & fees
Oct 5 - Oct 6
The WOODS Shipping Container Cabin-High Speed WiFi!-Hot Tub!-Covered Deck!-RELAX
UPSCALE Shipping Container Cabin-Private-High Speed WIFI!-Hot Tub!-In The Woods!
Exterior

UPSCALE Shipping Container Cabin-Private-High Speed WIFI!-Hot Tub!-In The Woods!

10.0 out of 10, Exceptional, (145)
"We really enjoyed staying here! Hopefully we’ll be back some day!"
The price is ￥21,592
￥39,423 total
includes taxes & fees
Sep 28 - Sep 29
UPSCALE Shipping Container Cabin-Private-High Speed WIFI!-Hot Tub!-In The Woods!
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.
Interior

Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.

9.8 out of 10, Exceptional, (44)
"The pool was awesome!!! We spent hours in the pool. The house is bigger than it looks in the pictures and had everything we needed. Close to town with all the shopping you need but felt like it was out in the country."
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.
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

Hilton Lexington/Downtown

Hilton Lexington/Downtown

10/10 Excellent
"Great location. Close to all the good attractions "
Eric 1-night trip
Posted 4 days ago
Hilton Lexington/Downtown

Find out more about Winchester

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 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?

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.: Visitors like this Winchester vacation home rental. It is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge to make your meal-planning easier.

How many vacation rentals are there in Winchester?

Expedia has 7 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Lykins Park and College Park 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 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.