Search Cottages in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Winchester cottages

Property grounds
The Vue - Mountain top hot tub overlooking the Shenandoah River

The Vue - Mountain top hot tub overlooking the Shenandoah River

The Vue - Mountain top hot tub overlooking the Shenandoah River
2.0 star property
Front Royal
9.8 out of 10, Exceptional, (10)
"We rented this property to do an away game night with friends and it was great. The set up was perfect. The view is stunning. The central space both upstairs (kitchen and living room) and downstairs are very open, leaving a great ability to interact with each other. Everything we needed was there, the beds were super comfortable. Also, I'm always nervous renting on here out of fear that the host won't communicate enough. That was never an issue. Josefine made sure we had the instructions...
United States
Anonymous traveler
The price is AED 627
AED 1,445 total
includes taxes & fees
11 Dec - 12 Dec
The Vue - Mountain top hot tub overlooking the Shenandoah River
Property grounds
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Front Royal
10.0 out of 10, Exceptional, (2)
"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"
United States
Jay L.
The price is AED 489
AED 1,431 total
includes taxes & fees
16 Dec - 17 Dec
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Exterior
1800s Cozy Kitchen House in Berryville

1800s Cozy Kitchen House in Berryville

1800s Cozy Kitchen House in Berryville
2.0 star property
Berryville
The price is AED 529
AED 681 total
includes taxes & fees
11 Dec - 12 Dec
1800s Cozy Kitchen House in Berryville
House (Multiple Bedrooms) | Interior
'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
The price is AED 3,989
AED 6,711 total
includes taxes & fees
12 Dec - 13 Dec
'thomson Farm' Classic Home < 10 Mi to Vineyards!
Outdoor spa tub
Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (53)
"It was a beautiful getaway from all of the busy mess from our normal lives"
United States
Tailor N.
The price is AED 255
AED 889 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Retreat - Hot tub + Mountain Views + Pets
Exterior
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Berkeley Springs
9.4 out of 10, Exceptional, (19)
"Can't wait to come back to this beautiful home with my family! Amazing experience! "
United States
Brandon L.
The price is AED 547
AED 1,529 total
includes taxes & fees
11 Dec - 12 Dec
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
1 bedroom, WiFi, bed sheets
The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (43)
"The place was super cute and clean. It was the perfect little getaway spot for my husband and I’s anniversary. "
United States
Holly W.
The price is AED 360
AED 626 total
includes taxes & fees
16 Dec - 17 Dec
The Carriage House at Carrot Top Cottage
Terrace/patio
Wild Hare Cottage

Wild Hare Cottage

Wild Hare Cottage
Purcellville
10.0 out of 10, Exceptional, (10)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
United States
Jennifer K.
The price is AED 463
AED 808 total
includes taxes & fees
17 Dec - 18 Dec
Wild Hare Cottage
Property grounds
Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (30)
"What a great weekend we had! This cottage had everything you could possibly want for a weekend getaway. "
United States
Elaine H.
The price is AED 367
AED 1,337 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful Lakefront Cottage with Mountain Views!
Outdoor dining
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (23)
"My friends and I absolutely loved this stay on the lake in West Virginia! The artsy vibe of the home, views, and wildlife were amazing. Plenty of places to sit and catch up. The kitchen was well stocked with appliances (thank you for the local coffee!) Each adult having their own bedroom and full bath was a huge perk!"
United States
Matthew P.
The price is AED 404
AED 1,648 total
includes taxes & fees
18 Dec - 19 Dec
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds
Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (21)
"The house was clean, had plenty of rooms and a fantastic location. "
United States
Bryan N.
The price is AED 367
AED 1,320 total
includes taxes & fees
11 Dec - 12 Dec
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds
Cottage w/ Hot Tub and 100-Mile Valley Views!

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, (20)
"Great view, very secluded"
United States
Matt s.
The price is AED 367
AED 1,386 total
includes taxes & fees
18 Dec - 19 Dec
Cottage w/ Hot Tub and 100-Mile Valley Views!
Exterior
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (20)
"Really nice property, and exactly as advertised. There were several local restaurants within easy walking distance (we loved both Bolivar Bread and Snallygaster's) and it was a fairly easy walk to the historic part of Harper's Ferry. We also enjoyed the fire pit in the back yard."
United States
Greg B.
The price is AED 606
AED 1,109 total
includes taxes & fees
4 Jan - 5 January 2026
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior
Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.6 out of 10, Exceptional, (10)
"The setting is peaceful and beautiful. The property has a rich history. The house has a lot of quirky character and exploring it is a trip within itself. We have stayed in several places in WV but this one is currently our favorite."
United States
Gregory S.
The price is AED 737
AED 1,167 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful Waterfall House -- 2 bedroom hidden treasure
Exterior
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.4 out of 10, Exceptional, (6)
"We enjoyed our stay , close to everything we planned for the weekend. Place was very roomy, clean and the beds were very comfortable!!"
United States
Cheryl O.
The price is AED 469
AED 1,985 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Property grounds
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

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

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.6 out of 10, Exceptional, (9)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
The price is AED 826
AED 1,440 total
includes taxes & fees
14 Dec - 15 Dec
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio
Woodsy Retreat with a Hot Tub and Seasonal Views!

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, (24)
"I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance."
United States
Claudia F.
The price is AED 367
AED 1,255 total
includes taxes & fees
17 Dec - 18 Dec
Woodsy Retreat with a Hot Tub and Seasonal Views!
Interior
Hike, Sip & Explore: Charming Waterford Cottage!

Hike, Sip & Explore: Charming Waterford Cottage!

Hike, Sip & Explore: Charming Waterford Cottage!
3.0 star property
Waterford
The price is AED 1,010
AED 1,779 total
includes taxes & fees
30 Dec - 31 Dec
Hike, Sip & Explore: Charming Waterford Cottage!
Fridge, microwave, oven, stovetop
Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (37)
"The property was perfect for our stay. We had everything we needed and the beds were very comfy. We will definitely stay here again!"
United Kingdom
Andrew N.
The price is AED 788
AED 1,738 total
includes taxes & fees
11 Dec - 12 Dec
Royal Heritage Home @ Historic Leesburg
Exterior
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

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

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (81)
"Great place. Really enjoyed our mountain getaway!"
United States
Evan C.
The price is AED 588
AED 1,160 total
includes taxes & fees
5 Jan - 6 January 2026
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Great hotel!"
CHARLES 1-night trip
Posted 3 days ago
The George Washington Hotel, A Wyndham Grand Hotel

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that vacations 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 favorite 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.