Search Winchester Cottage Rentals from CA $139

  • 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

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Cottage image
Cottages
Cottages

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is CA $208
CA $286 total
includes taxes & fees
Nov 8 - Nov 9
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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, (28 reviews)
"Enjoyed our stay, house was beautiful and clean. Coffee in the morning with the deer was awesome. Love the neighborhood cat Luna."
United States
Kevin D.
The price is CA $435
CA $810 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $409
CA $551 total
includes taxes & fees
Nov 8 - Nov 9
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
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.
The price is CA $513
CA $900 total
includes taxes & fees
Nov 8 - Nov 9
Mountain View Cottage | Hot Tub & Game Room
A covered porch with a table and chairs, large windows, and a ceiling fan.

5. 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 CA $581
CA $664 total
includes taxes & fees
Nov 8 - Nov 9
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.

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.
The price is CA $351
CA $750 total
includes taxes & fees
Dec 1 - Dec 2
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, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is CA $168
CA $293 total
includes taxes & fees
Nov 8 - Nov 9
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)
"The property was absolutely beautiful. The view of the lake was so pretty. Communication with the host was wonderful very informative. Very cozy and the house was beautiful inside."
United States
Tara G.
The price is CA $140
CA $622 total
includes taxes & fees
Nov 18 - Nov 19
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, (29 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 CA $172
CA $696 total
includes taxes & fees
Nov 18 - Nov 19
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A two-story house with a front lawn and trees in the background.

10. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is CA $169
CA $496 total
includes taxes & fees
Nov 19 - Nov 20
Walk to Stores: Home in Historic Shepherdstown!
A modern building with large windows, a deck, and a stone wall.

11. 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 CA $140
CA $572 total
includes taxes & fees
Nov 19 - Nov 20
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub with a view of a forested landscape during sunset.

12. 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, (29 reviews)
"My husband and I went for a short trip. The communication was great and the house was perfect! We spent most of our time in the hot tub checking out the amazing view."
United States
Keri L.
The price is CA $163
CA $610 total
includes taxes & fees
Nov 16 - Nov 17
Cottage w/ Hot Tub and 100-Mile Valley Views!
A bedroom with a bed, a table, and a view of the outdoors.

13. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (55 reviews)
"Very clean and convenient for seeing Harpers Ferry"
United States
Rich C.
The price is CA $195
CA $294 total
includes taxes & fees
Nov 12 - Nov 13
The Carriage House at Carrot Top Cottage
A wooden deck with a glass railing overlooking a forested area.

14. Round House w Mountain View Hot Tub

Round House w Mountain View Hot Tub
Luray
10.0 out of 10, Exceptional, (1 review)
The price is CA $181
CA $408 total
includes taxes & fees
Nov 16 - Nov 17
Round House w Mountain View Hot Tub
A stone house with a chimney, surrounded by a well-maintained lawn and trees.

15. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (68 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is CA $405
CA $553 total
includes taxes & fees
Nov 15 - Nov 16
18th Century Stone Cottage minutes from historic Middleburg
A white building with a red roof and a chimney, surrounded by trees and grassy area.

16. 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 CA $280
CA $425 total
includes taxes & fees
Nov 8 - Nov 9
Peaceful Waterfall House -- 2 bedroom hidden treasure
Exterior

17. 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 CA $598
CA $725 total
includes taxes & fees
Nov 9 - Nov 10
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
A wooden deck with a table and chairs, overlooking a forested area with string lights.

18. 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 CA $236
CA $566 total
includes taxes & fees
Nov 10 - Nov 11
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
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, (36 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.
The price is CA $272
CA $456 total
includes taxes & fees
Nov 12 - Nov 13
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
An outdoor patio with Adirondack chairs and a fire pit, surrounded by a forested area.

20. 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 CA $245
CA $459 total
includes taxes & fees
Nov 8 - Nov 9
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
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

Winchester and related destinations

Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre.

See all hotels in Winchester
A white neoclassical building with columns, an American flag, and a clock tower.

Top reviews in Winchester

A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester

10/10 Excellent

Nice quiet clean
Canada
Fay
Reviewed February 8, 2024
Comfort Inn & Suites Winchester

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.

Explore a world of travel with Expedia