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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester cottages

A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

1. 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.
$199 nightly
The price is $219
Sep 29 - Sep 30
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

2. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (16 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
$370 nightly
The price is $411
Sep 29 - Sep 30
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A hot tub under a wooden pergola with a grassy yard and trees in the background.

3. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.6 out of 10, Exceptional, (39 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
$645 nightly
The price is $712
Oct 22 - Oct 23
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A hot tub on an outdoor deck with a view of trees and hills.

4. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
$611 nightly
The price is $674
Sep 29 - Sep 30
Total with taxes and fees
Mountain View Cottage | Hot Tub & Game Room
A covered outdoor area with a fire pit, seating, and a view of the landscape.

5. Mountain View Cottage with Hot Tub and River Views

Mountain View Cottage with Hot Tub and River Views
Front Royal
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...
United States
MaryBeth C.
$610 nightly
The price is $673
Sep 30 - Oct 1
Total with taxes and fees
Mountain View Cottage with Hot Tub and River Views
A covered outdoor area with a fire pit, seating, and a view of the landscape.

6. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (27 reviews)
"Excellent location and amazing reviews. Would definitely plan to arrive while it’s light out for the first time as the road does get a little rough at the top but we did all make it in 2WD vehicles"
United States
Sara Z.
$592 nightly
The price is $653
Sep 27 - Sep 28
Total with taxes and fees
Mountaintop Cottage | Private Hot Tub
A modern building with large windows, a deck, and a stone wall.

7. 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, (28 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
$345 nightly
The price is $385
Sep 27 - Sep 28
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

8. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (28 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
United States
Lindy K.
$431 nightly
The price is $481
Sep 30 - Oct 1
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A living room with a dining table, chairs, a sofa, and a television.

9. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
$195 nightly
The price is $217
Oct 1 - Oct 2
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A hot tub with a view of a forested landscape during sunset.

10. 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, (27 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveler
$362 nightly
The price is $404
Oct 12 - Oct 13
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
A white building with a red roof and a chimney, surrounded by trees and grassy area.

11. Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.8 out of 10, Exceptional, (16 reviews)
"House was great, though a little cold for the winter. Perfect place to get away! "
United States
Krystal A.
$271 nightly
The price is $302
Sep 28 - Sep 29
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure
A bedroom with a bed, a table, and a view of the outdoors.

12. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful location. Very peaceful and convenient for everything we wanted to do on our trip. Enjoyed all the deer while sitting outside the cottage reading."
United States
Clinton R.
$205 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
The Carriage House at Carrot Top Cottage
A stone house with a chimney, surrounded by a well-maintained lawn and trees.

13. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (66 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
$348 nightly
The price is $373
Sep 30 - Oct 1
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
A wooden deck with a table and chairs, overlooking a forested area with string lights.

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

Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
Berkeley Springs
10.0 out of 10, Exceptional, (5 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.
$367 nightly
The price is $409
Sep 27 - Sep 28
Total with taxes and fees
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
A two-story house with a covered porch and a wooden fence.

15. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
$313 nightly
The price is $350
Sep 27 - Sep 28
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

16. 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, (26 reviews)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
$326 nightly
The price is $372
Sep 27 - Sep 28
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
An outdoor patio with Adirondack chairs and a fire pit, surrounded by a forested area.

17. Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
3.0 star property
Luray
$290 nightly
The price is $334
Sep 27 - Sep 28
Total with taxes and fees
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
A single-story house with a gabled roof, a front porch with a bench, and a front door.

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

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (107 reviews)
"Great place to stay and very responsive owners to any questions"
United States
Tracy B.
$262 nightly
The price is $302
Sep 27 - Sep 28
Total with taxes and fees
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

19. Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia

Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
The Woods
$343 nightly
The price is $364
Sep 27 - Sep 28
Total with taxes and fees
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia

20. Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia

Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
Bolivar
$482 nightly
The price is $512
Oct 1 - Oct 2
Total with taxes and fees
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
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

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

10/10 Excellent
"."
Michael 1-night trip
Posted 8 hours ago
Candlewood Suites Winchester by IHG

Find out more about Winchester

Winchester Cottages information

Number of reviews
460
Accommodation
192 Cottages
Lowest Price
$217
Highest Price
$712

Frequently asked questions

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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.
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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 Harbor 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.

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