Search Vacation Homes in Winchester
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Winchester holiday homes
The Apple Mountain House
The Apple Mountain HouseFront Royal
9.6 out of 10, Exceptional, (10 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
Katia R.
The price is HK$732
HK$2,660 total
includes taxes & fees
9 Feb - 10 Feb
Lamontagne Farmhouse a Rural Pristine Setting
Lamontagne Farmhouse a Rural Pristine SettingBluemont
10.0 out of 10, Exceptional, (12 reviews)
"We loved our stay at this beautiful tranquil farmhouse. Our two Golden’s enjoyed the outdoor space. Hiking close by, a beautiful drive to visit Middleburg is a must. We highly recommend this charming getaway."
AnneMarie M.
Mountain View Bungalow in Front Royal
Mountain View Bungalow in Front RoyalFront Royal
10.0 out of 10, Exceptional, (13 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
Brian B.
The price is HK$1,054
HK$1,730 total
includes taxes & fees
5 Feb - 6 Feb
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + WineriesLinden
10.0 out of 10, Exceptional, (22 reviews)
"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "
Katelyn E.
The price is HK$907
HK$2,353 total
includes taxes & fees
4 Feb - 5 Feb
Newly renovated Farm cottage with Mountain views
Newly renovated Farm cottage with Mountain viewsStrasburg
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
Shannon H.
The price is HK$1,250
HK$2,533 total
includes taxes & fees
15 Feb - 16 Feb
Historic Bluemont Village Home
Historic Bluemont Village HomeBluemont
10.0 out of 10, Exceptional, (39 reviews)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
Mary S.
Welcome to the Ladybug Retreat!
Welcome to the Ladybug Retreat!Boyce
10.0 out of 10, Exceptional, (1 review)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
Catherine A.
The price is HK$1,367
HK$3,162 total
includes taxes & fees
5 Feb - 6 Feb
Big Sunny Family House
Big Sunny Family HouseFront Royal
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful house and town! Loved every minute of our trip! "
MaryAnn G.
The price is HK$1,320
HK$3,338 total
includes taxes & fees
3 Mar - 4 Mar
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.
Find holiday rentals that suit your style
Apartments
Private holiday homes
Save an average of 15% on thousands of hotels when you're signed in
Top Winchester Hotel Reviews
SpringHill Suites by Marriott Winchester
10/10 Excellent
Find out more about Winchester
Winchester Vacation Homes information
Number of reviews | 316 |
|---|---|
Accommodation | 632 Vacation Homes |
Lowest Price | HK$1,621 |
Highest Price | HK$12,156 |