Photo by Hyelsinta
Find Cabins in Winchester for Rent from CA $100
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Winchester Cabin Rentals

Natural Bridge State Resort Park
Natural Bridge State Resort Park
8.6 out of 10, Excellent, (1668)
The price is CA $132
CA $146 total
includes taxes & fees
Sep 1 - Sep 2

Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
9.0 out of 10, Wonderful, (158)

Hot Tub, WiFi, No Pet Fee - Beary Cozy - Romantic Cabin in Red River Gorge, Kentucky!
Hot Tub, WiFi, No Pet Fee - Beary Cozy - Romantic Cabin in Red River Gorge, Kentucky!
8.8 out of 10, Excellent, (106)
The price is CA $226
CA $394 total
includes taxes & fees
Aug 25 - Aug 26

Tranquil Getaway in the Woods ~ Sunset Ridge
Tranquil Getaway in the Woods ~ Sunset Ridge
9.8 out of 10, Exceptional, (64)
The price is CA $143
CA $203 total
includes taxes & fees
Aug 25 - Aug 26

"ENDLESS VIEW" Red River Gorge/Natural Bridge- New Construction!! Dog Friendly!!
"ENDLESS VIEW" Red River Gorge/Natural Bridge- New Construction!! Dog Friendly!!
10.0 out of 10, Exceptional, (62)

Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
8.4 out of 10, Very good, (123)
The price is CA $149
CA $298 total
includes taxes & fees
Aug 24 - Aug 25

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
10.0 out of 10, Exceptional, (26)
The price is CA $235
CA $292 total
includes taxes & fees
Aug 21 - Aug 22

Tanzanite-- The "GEM" with a Hot Tub & WiFi!!
Tanzanite-- The "GEM" with a Hot Tub & WiFi!!
9.6 out of 10, Exceptional, (42)
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Winchester Hotel Reviews

Embassy Suites by Hilton Lexington/UK Coldstream
10/10 Excellent
Find out more about Winchester
Find out more about Winchester
Winchester Cabin Rentals information
Number of reviews | 2,756 |
---|---|
Accommodation | 253 Cabin Rentals |
Lowest Price | CA $100 |
Highest Price | CA $235 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Cabin Rentals in Other Destinations
More Accommodation Types in Winchester
- Vacation Homes in Winchester
- Apartments in Winchester
- Condo Rentals in Winchester
- Cottages in Winchester
- Farmstay in Winchester
- Motels in Winchester
- RV Parks in Winchester
- Lodges in Winchester
- B&B in Winchester
- Chalets in Winchester
- Guest Houses in Winchester
- Resorts in Winchester
- Villas in Winchester
- Hotels
All Accommodation Types
Be inspired: Top Cabin Rentals destinations in 2025
- Jasper National Park Cabins
- Tofino Cabins
- Algonquin Park Cabins
- Cultus Lake Cabins
- Waterton Park Cabins
- Squamish Cabins
- Sunshine Coast Cabins
- Hope Cabins
- Radium Hot Springs Cabins
- Kananaskis Cabins
- Jasper Cabins
- Revelstoke Cabins
- Harrison Hot Springs Cabins
- Calgary Cabins
- Canmore Cabins
- Chilliwack Cabins
- Northern Ontario Cabins
- Fernie Cabins
- Kenora Cabins
- Drumheller Cabins
More ways to book
Expedia's Latest Trends
Hotels
- NHHotels Hotels in Málaga
- Vacation Homes Orlando
- Downtown Montreal Luxury Hotels
- Fort Ilocandia Resort Hotel
- Huntsville Inn
- Hotels in Little Italy
- Hotels in Mount Hope
- Milan All Inclusive Resorts and Hotels
- Cancun All Inclusive Resorts and Hotels
- Secrets Akumal Riviera Maya - Adults Only - All Inclusive
- HyattHotels Hotels in Rocky Mountains
- Hotels in Salt Spring Island
- Blue Mountain Resort Village Suites
- Downtown Vancouver Casino Hotels
Flights
- Flights from Madison to Calgary
- Allegiant Air
- Flights to Yuba City
- Flights from Victoria to Kansas City
- Flights from Myrtle Beach to Ottawa
- Flights from Toronto to Montreal
- Flights from Toronto to Portland
- Flights from Windsor to Punta Cana
- Flights from Calgary to Green Bay
- Flights from Sault Ste. Marie to Tampa
General