An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

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, (9 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is AED 545
AED 1,124 total
includes taxes & fees
22 Jun - 23 Jun
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 AED 545
AED 1,124 total
includes taxes & fees
23 Jun - 24 Jun
The Winchester
Fridge, microwave, oven, stovetop

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (50 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is AED 327
AED 779 total
includes taxes & fees
28 Jun - 29 Jun
Conveniently Located ~ WiFi ~ Central Heat & Air.
Exterior

Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3

Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3
Stanton
9.4 out of 10, Exceptional, (13 reviews)
"Exactly as advertised and management was super responsive "
United States
Chris H.
The price is AED 218
AED 483 total
includes taxes & fees
22 Jun - 23 Jun
Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3
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, (1,933 reviews)
"Great area Nice place to stay"
United States
Julie
The price is AED 449
AED 495 total
includes taxes & fees
19 Jul - 20 Jul
Natural Bridge State Resort Park
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, (324 reviews)
"Great stay! Loved the private driveway. "
United States
Emily N.
The price is AED 659
AED 1,156 total
includes taxes & fees
23 Jun - 24 Jun
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
House (1 Bedroom) | Interior

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: 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
The price is AED 496
AED 1,148 total
includes taxes & fees
22 Jun - 23 Jun
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Terrace/patio

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (36 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is AED 479
AED 694 total
includes taxes & fees
22 Jun - 23 Jun
Mountaintop Cottage
TV, fireplace

Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.

Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.
Slade
8.2 out of 10, Very Good, (30 reviews)
"The home had a great view and was very close to anything you'd love to do in the area. "
United States
Caleb H.
Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.
Interior

East Suite-🕊️ at Bleubird Studio, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Georgetown
10.0 out of 10, Exceptional, (66 reviews)
"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "
United States
l v.
The price is AED 459
AED 830 total
includes taxes & fees
29 Jun - 30 Jun
East Suite-🕊️ at Bleubird Studio, Walk to Downtown
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, (109 reviews)
"This was a wonderful location and a delightfully cozy cabin for a couple or a solo stay. Might very well stay here again in the future."
United States
Jason H.
The price is AED 324
AED 709 total
includes taxes & fees
5 Jul - 6 Jul
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Terrace/patio

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (48 reviews)
"The cabin was perfect for us! It was comfortable and had everything we needed. The back porch was awesome with a gorgeous view! "
United States
Patrece M.
The price is AED 625
AED 786 total
includes taxes & fees
22 Jun - 23 Jun
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
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, (131 reviews)
"Cute little spot to stay, the view and hot tub is incredible, both day & night. "
United States
Tawny Freber- S.
The price is AED 590
AED 1,039 total
includes taxes & fees
22 Jun - 23 Jun
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Terrace/patio

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (77 reviews)
"Would stay again. Responsive host, property was very clean and host had left nice touches / decorations for valentines day weekend visit."
United States
Robert C.
The price is AED 496
AED 717 total
includes taxes & fees
22 Jun - 23 Jun
Mountain Memories Cabin
Interior

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Stanton
10.0 out of 10, Exceptional, (367 reviews)
"Great spot for weekend getaway. "
United States
Liz A.
The price is AED 621
AED 1,105 total
includes taxes & fees
25 Jun - 26 Jun
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Dining

PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB

PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
Stanton
10.0 out of 10, Exceptional, (27 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is AED 590
AED 1,039 total
includes taxes & fees
22 Jun - 23 Jun
PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
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, (6 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 AED 507
AED 1,004 total
includes taxes & fees
22 Jun - 23 Jun
"Cardinal Crest" - Overlook Dome 002 in RRG
Property grounds

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (165 reviews)
"Everything was amazing Highly Recommend"
United States
Jason L.
The price is AED 590
AED 1,047 total
includes taxes & fees
23 Jun - 24 Jun
STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
Smart TV, fireplace, books

Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (112 reviews)
"This is a unique property, it feels like stepping into history. It is well maintained, clean and comfortable but not your average stay! "
United States
Jennie C.
The price is AED 349
AED 661 total
includes taxes & fees
22 Jun - 23 Jun
Unique Stay in a 1907 Log Cabin on The Kentucky River
Fridge, microwave, stovetop, dishwasher

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (13 reviews)
"Fun place to stay for 2!"
United States
Bob R.
The price is AED 441
AED 1,157 total
includes taxes & fees
22 Jun - 23 Jun
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Check-In was very good and helpful👍. Room was large and clean. Overall a very positive experience."
Matthew 2-night trip
Posted 1 hour ago
Elwood Hotel & Suites

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?

Luxe Home Downtown - Sleeps 6. Off-street parking: Visitors like this Winchester vacation home rental. It is located in the city center 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Winchester?

Expedia has 5 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Community Park and The Holler are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Wiseman Park and Winchester Traveling Trail 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.