A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Search Cottages in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Winchester cottages

Exterior

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is HK$1,165
HK$1,769 total
includes taxes & fees
30 Jun - 1 Jul
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Terrace/patio

All-Inclusive 4BR | Mountain Views | Hot Tub

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
The price is HK$1,796
HK$4,498 total
includes taxes & fees
15 Jul - 16 Jul
All-Inclusive 4BR | Mountain Views | Hot Tub
Terrace/patio

Apple Mountain House | Hot Tub | Game Room

Apple Mountain House | Hot Tub | Game Room
Front Royal
9.6 out of 10, Exceptional, (14 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is HK$1,749
HK$4,437 total
includes taxes & fees
27 Jul - 28 Jul
Apple Mountain House | Hot Tub | Game Room
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (14 reviews)
"Excellent place to stay. Shelly is an excellent host. Nice location "
United States
Lisa H.
The price is HK$2,294
HK$3,417 total
includes taxes & fees
30 Jun - 1 Jul
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

The VUE | Mountaintop 4BR | Hot Tub & Views

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (23 reviews)
"We had such a great experience staying at The Vue! The home was incredibly well cared for, and everything matched the listing perfectly which made planning our trip so much easier. Check-in was smooth and stress-free, and the host did a fantastic job providing all the information we needed ahead of time. It truly felt like a 10/10 stay, and we’d love to come back!"
United States
David S.
The price is HK$2,651
HK$5,138 total
includes taxes & fees
5 Jul - 6 Jul
The VUE | Mountaintop 4BR | Hot Tub & Views
Outdoor spa tub

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (68 reviews)
"We enjoyed the hot tub, the views, and the easy check in/check out."
United States
Dakota B.
The price is HK$786
HK$2,225 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Retreat - Hot tub + Mountain Views + Pets
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (24 reviews)
"Great view, very secluded"
United States
Matt s.
The price is HK$980
HK$3,247 total
includes taxes & fees
1 Jul - 2 Jul
Cottage w/ Hot Tub and 100-Mile Valley Views!
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (23 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
The price is HK$784
HK$2,812 total
includes taxes & fees
6 Jul - 7 Jul
Lake View Retreat - Cottage Near a Peaceful Lake!
Exterior

Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is HK$784
HK$2,679 total
includes taxes & fees
29 Jun - 30 Jun
Woodsy Retreat with a Hot Tub and Seasonal Views!
Exterior

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (99 reviews)
"Highly recommend! Great location."
United States
Daren E.
The price is HK$1,192
HK$2,505 total
includes taxes & fees
29 Jun - 30 Jun
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (26 reviews)
"The host was prompt with answering any inquiries. The house was well stocked. Great area to visit."
United States
Ellen B.
The price is HK$1,427
HK$4,336 total
includes taxes & fees
29 Jun - 30 Jun
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (62 reviews)
"Loved out stay! "
United States
Emilee
The price is HK$2,157
HK$3,130 total
includes taxes & fees
2 Jul - 3 Jul
18th Century Stone Cottage minutes from historic Middleburg
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (50 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is HK$972
HK$1,256 total
includes taxes & fees
19 Jul - 20 Jul
The Carriage House at Carrot Top Cottage
Terrace/patio

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (22 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
The price is HK$1,764
HK$3,120 total
includes taxes & fees
6 Jul - 7 Jul
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (28 reviews)
"Great house and location! "
United States
Johanna S.
The price is HK$1,712
HK$2,903 total
includes taxes & fees
1 Jul - 2 Jul
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.8 out of 10, Exceptional, (13 reviews)
"House was great, though a little cold for the winter. Perfect place to get away! "
United States
Krystal A.
The price is HK$1,749
HK$2,689 total
includes taxes & fees
14 Jul - 15 Jul
Peaceful Waterfall House -- 2 bedroom hidden treasure
Outdoor dining

Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room

Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
"One of the best properties I’ve rented. Everything was better than described and the description was already stellar. Highly recommend and will likely rent again. "
United States
Cyndi P.
The price is HK$1,226
HK$3,337 total
includes taxes & fees
5 Jul - 6 Jul
Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (42 reviews)
"Awesome spot, truly walking distance to all the cool little downtown stuff. Host was kind and there wasn't almost any check out procedure! "
United States
Charles K.
The price is HK$1,768
HK$3,741 total
includes taxes & fees
29 Jun - 30 Jun
Royal Heritage Home @ Historic Leesburg
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

10/10 Excellent
"The rooms are big and spacious. The beds were nice and comfortable. The pillows were out of this world. 4 per bed. Very clean. We diffently will be back. Good job everyone!"
Charles 1-night trip
Posted less than an hour ago
Candlewood Suites Winchester by IHG

Find out more about Winchester

Winchester Cottages information

Number of reviews
485
Accommodation
191 Cottages
Lowest Price
HK$1,256
Highest Price
HK$5,138

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that holidays should be simple, so if you're in search of cottages in Winchester at a competitive price, Expedia has got your back. Keep costs down and check in to a cheap option far away from the city rush, or splurge on an upmarket cottage to spoil your favourite people.
How can I find cheap cottages in Winchester?
The easiest way to locate cheap cottages in Winchester is with Expedia's useful filter tool. Narrow your search results by star rating, amenities and budget to snag awesome prices in just a few keystrokes.
What is there to do in Winchester near my cottage?
Winchester has enough activities and sights to keep you on the hop for weeks, starting with Rock Harbour Golf Course. The Kernstown Battlefield, Museum of the Shenandoah Valley and Apple Blossom Mall are other fantastic attractions. If you're in town a while, Jim Barnett Park and Handley Regional Library are nice final touches to your itinerary.

Explore a world of travel with Expedia