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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester cottages

A hot tub under a wooden pergola with a grassy yard and trees in the background.

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

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is €595
includes taxes & fees
22 Oct - 23 Oct
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A covered outdoor area with a fire pit, seating, and a view of the landscape.

2. 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.
The price is €553
includes taxes & fees
15 Oct - 16 Oct
Mountaintop Cottage | Private Hot Tub
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

3. 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
The price is €384
includes taxes & fees
26 Oct - 27 Oct
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

4. 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
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is €206
includes taxes & fees
27 Oct - 28 Oct
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A hot tub on an outdoor deck with a view of trees and hills.

5. 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.
The price is €597
includes taxes & fees
15 Oct - 16 Oct
Mountain View Cottage | Hot Tub & Game Room
A two-story house with a wooden deck, surrounded by lush greenery.

6. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Front Royal
The price is €434
includes taxes & fees
28 Oct - 29 Oct
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
A covered outdoor area with a fire pit, seating, and a view of the landscape.

7. 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.
The price is €597
includes taxes & fees
15 Oct - 16 Oct
Mountain View Cottage with Hot Tub and River Views
A living room with a dining table, chairs, a sofa, and a television.

8. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is €199
includes taxes & fees
18 Oct - 19 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A hot tub on a deck with a view of a lake and forest.

9. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
The price is €416
includes taxes & fees
19 Oct - 20 Oct
Peaceful Lakefront Cottage with Mountain Views!
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, (28 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveller
The price is €372
includes taxes & fees
29 Oct - 30 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

11. 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.
The price is €453
includes taxes & fees
21 Oct - 22 Oct
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A modern building with large windows, a deck, and a stone wall.

12. 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, (29 reviews)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
United States
Rebecca N.
The price is €308
includes taxes & fees
21 Oct - 22 Oct
Woodsy Retreat with a Hot Tub and Seasonal Views!
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, (67 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is €359
includes taxes & fees
18 Oct - 19 Oct
18th Century Stone Cottage minutes from historic Middleburg
A white building with a red roof and a chimney, surrounded by trees and grassy area.

14. Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.6 out of 10, Exceptional, (17 reviews)
"House was great, though a little cold for the winter. Perfect place to get away! "
United States
Krystal A.
The price is €290
includes taxes & fees
21 Oct - 22 Oct
Peaceful Waterfall House -- 2 bedroom hidden treasure
A bedroom with a bed, a table, and a view of the outdoors.

15. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (54 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is €199
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage
Living area

16. 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
The price is €447
includes taxes & fees
19 Oct - 20 Oct
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

17. 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)
"Fun place to stay!!!"
United States
Theresa R.
The price is €358
includes taxes & fees
15 Oct - 16 Oct
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.

18. 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
The price is €299
includes taxes & fees
21 Oct - 22 Oct
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
A wooden deck with a table and chairs, overlooking a forested area with string lights.

19. 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.
The price is €390
includes taxes & fees
27 Oct - 28 Oct
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Friendly, professional staff. Most helpful with an issue I had with my car. Could not have been nicer and understanding."
DOUGLAS 2-night trip
Posted 4 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Find out more about Winchester

Winchester Cottages information

Number of reviews
396
Accommodation
194 Cottages
Lowest Price
€199
Highest Price
€597

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?
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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 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.