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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester cottages

Exterior

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.
$203 nightly
The price is $223
Sep 21 - Sep 22
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Exterior

2. 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
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Terrace/patio

3. 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.
$621 nightly
The price is $685
Sep 22 - Sep 23
Total with taxes and fees
Mountain View Cottage | Hot Tub & Game Room
Outdoor spa tub

4. 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
$392 nightly
The price is $436
Sep 21 - Sep 22
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

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.
$641 nightly
The price is $707
Sep 29 - Sep 30
Total with taxes and fees
Mountain View Cottage with Hot Tub and River Views
Terrace/patio

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.
$628 nightly
The price is $693
Sep 20 - Sep 21
Total with taxes and fees
Mountaintop Cottage | Private Hot Tub
Exterior

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.
$306 nightly
The price is $341
Oct 1 - Oct 2
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
Outdoor spa tub

8. 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
$343 nightly
The price is $382
Sep 21 - Sep 22
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor dining

9. 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.
$417 nightly
The price is $464
Sep 21 - Sep 22
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Terrace/patio

10. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (40 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.
$389 nightly
The price is $433
Sep 22 - Sep 23
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
Dining

11. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Host let us in a bit early which was nice!"
United States
John
$211 nightly
The price is $235
Sep 21 - Sep 22
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
Exterior

12. 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.
$287 nightly
The price is $319
Sep 22 - Sep 23
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure
Outdoor dining

13. 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.
$386 nightly
The price is $430
Sep 20 - Sep 21
Total with taxes and fees
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
Exterior

14. 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.
$370 nightly
The price is $397
Sep 30 - Oct 1
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
Exterior

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.
$334 nightly
The price is $372
Sep 21 - Sep 22
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
1 bedroom, WiFi, bed sheets

16. 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.
$201 nightly
The price is $224
Oct 4 - Oct 5
Total with taxes and fees
The Carriage House at Carrot Top Cottage
Terrace/patio

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)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
$346 nightly
The price is $394
Sep 21 - Sep 22
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

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.
$273 nightly
The price is $315
Sep 21 - Sep 22
Total with taxes and fees
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
House (2 Bedrooms) | Interior

19. 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 20 - Sep 21
Total with taxes and fees
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
TV, fireplace

20. 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
$364 nightly
The price is $386
Sep 20 - Sep 21
Total with taxes and fees
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in 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

8/10 Good
"Friendly young man at front desk. Clean hotel, very comfy beds and pillows and a lot of water pressure. Large room with kitchen and large fridge with a freezer."
Kimberley 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
421
Accommodation
192 Cottages
Lowest Price
$223
Highest Price
$707

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.
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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