Winchester Vacation Rentals

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Winchester Vacation Homes

Our top choices for Winchester vacation homes

Bear Necessities Cabin - What Else Do You Need?
Fridge, microwave, stovetop, coffee/tea maker

Bear Necessities Cabin - What Else Do You Need?

10.0 out of 10, Exceptional, (1)
"Great little spot! Cabin is super nice inside and out."
The price is CA $145
CA $256 total
includes taxes & fees
Aug 21 - Aug 22
Bear Necessities Cabin - What Else Do You Need?
Unique stay, hot tub, secluded
Interior

Unique stay, hot tub, secluded

9.4 out of 10, Exceptional, (11)
"Comfy beds and great hottub. It was so cute and unique to stay in a grain bin. Very nicely decorated and clean. "
The price is CA $169
CA $355 total
includes taxes & fees
Aug 25 - Aug 26
Unique stay, hot tub, secluded
King size Bed & Hot Tub in the country!
Property grounds

King size Bed & Hot Tub in the country!

The price is CA $271
CA $428 total
includes taxes & fees
Aug 21 - Aug 22
King size Bed & Hot Tub in the country!
LAKE HOUSE ON ROCKY FORK!
Property grounds

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (30)
"Perfect spot for my family to get together for Christmas! Easy to get to, cozy and nice backyard cause I have dogs. Just a great place to stay!"
The price is CA $248
CA $552 total
includes taxes & fees
Aug 24 - Aug 25
LAKE HOUSE ON ROCKY FORK!
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Fridge, microwave, oven, stovetop

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

9.4 out of 10, Exceptional, (3)
"This was a great stay. Very easy to find and in a good area. Very clean and nice. "
The price is CA $279
CA $379 total
includes taxes & fees
Aug 28 - Aug 29
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage
Fridge, microwave, oven, stovetop

Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage

The price is CA $436
CA $918 total
includes taxes & fees
Aug 25 - Aug 26
Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage
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

Beverly hills inn

Beverly hills inn

10/10 Excellent
"Awesome hosts"
Scott 1-night trip
Posted 1 day ago
Beverly hills inn