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

Our top choices for Winchester cottages

A covered outdoor area with a fire pit, seating, and a view of the landscape.

1. 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.
$562 nightly
The price is $620
Oct 15 - Oct 16
Total with taxes and fees
Mountaintop Cottage | Private Hot Tub
A two-story house with a wooden deck, surrounded by lush greenery.

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
$440 nightly
The price is $486
Oct 27 - Oct 28
Total with taxes and fees
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
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
$392 nightly
The price is $436
Oct 26 - Oct 27
Total with taxes and fees
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.
$204 nightly
The price is $224
Oct 27 - Oct 28
Total with taxes and fees
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.
$595 nightly
The price is $657
Oct 15 - Oct 16
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.

6. 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
Oct 15 - Oct 16
Total with taxes and fees
Mountain View Cottage with Hot Tub and River Views
A living room with a dining table, chairs, a sofa, and a television.

7. 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.
$199 nightly
The price is $221
Oct 18 - Oct 19
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A hot tub on a deck with a view of a lake and forest.

8. 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.
$411 nightly
The price is $458
Oct 19 - Oct 20
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

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.
$460 nightly
The price is $512
Oct 21 - Oct 22
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A modern building with large windows, a deck, and a stone wall.

10. 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.
$308 nightly
The price is $343
Oct 21 - Oct 22
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub with a view of a forested landscape during sunset.

11. 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 traveler
$366 nightly
The price is $408
Oct 29 - Oct 30
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
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, (54 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
$198 nightly
The price is $221
Nov 9 - Nov 10
Total with taxes and fees
The Carriage House at Carrot Top Cottage
A white building with a red roof and a chimney, surrounded by trees and grassy area.

13. 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.
$285 nightly
The price is $317
Oct 21 - Oct 22
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure
A stone house with a chimney, surrounded by a well-maintained lawn and trees.

14. 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.
$367 nightly
The price is $394
Oct 18 - Oct 19
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
Terrace/patio

15. 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
$454 nightly
The price is $505
Oct 19 - Oct 20
Total with taxes and fees
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
An outdoor patio with Adirondack chairs and a fire pit, surrounded by a forested area.

16. 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
Oct 21 - Oct 22
Total with taxes and fees
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.

17. 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.
$405 nightly
The price is $451
Oct 27 - Oct 28
Total with taxes and fees
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

18. 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.
$344 nightly
The price is $392
Oct 15 - Oct 16
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A two-story house with a covered porch and a wooden fence.

19. 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.
$305 nightly
The price is $340
Nov 3 - Nov 4
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A single-story house with a gabled roof, a front porch with a bench, and a front door.

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

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (110 reviews)
"Great place to stay and very responsive owners to any questions"
United States
Tracy B.
$282 nightly
The price is $325
Nov 3 - Nov 4
Total with taxes and fees
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.
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Top Winchester Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Modern hotel. Convenient on/off highway. Clean & comfortable"
Marian 1-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
499
Accommodation
197 Cottages
Lowest Price
$221
Highest Price
$673

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.
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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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