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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.
$492 nightly
The price is $543
Nov 18 - Nov 19
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

2. 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.
$194 nightly
The price is $213
Nov 16 - Nov 17
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.

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
$373 nightly
The price is $415
Nov 16 - Nov 17
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A covered outdoor area with a fire pit, seating, and a view of the landscape.

4. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (28 reviews)
"Amazing views"
United States
randall P.
$552 nightly
The price is $608
Nov 18 - Nov 19
Total with taxes and fees
Mountaintop Cottage | Private Hot Tub
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.
$613 nightly
The price is $676
Nov 16 - Nov 17
Total with taxes and fees
Mountain View Cottage | Hot Tub & Game Room
A covered porch with a table and chairs, large windows, and a ceiling fan.

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
$434 nightly
The price is $479
Nov 17 - Nov 18
Total with taxes and fees
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.
$445 nightly
The price is $491
Dec 1 - Dec 2
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.

8. 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
$189 nightly
The price is $211
Nov 22 - Nov 23
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
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.
$507 nightly
The price is $551
Nov 18 - Nov 19
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A hot tub on a deck with a view of a lake and forest.

10. 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.
$466 nightly
The price is $507
Nov 18 - Nov 19
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
A two-story house with a front lawn and trees in the background.

11. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
$335 nightly
The price is $355
Nov 19 - Nov 20
Total with taxes and fees
Walk to Stores: Home in Historic Shepherdstown!
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.
$445 nightly
The price is $484
Nov 18 - Nov 19
Total with taxes and fees
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, (68 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
$368 nightly
The price is $395
Nov 16 - Nov 17
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
A hot tub with a view of a forested landscape during sunset.

14. 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.
$466 nightly
The price is $507
Nov 23 - Nov 24
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.

15. 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.
$189 nightly
The price is $211
Nov 16 - Nov 17
Total with taxes and fees
The Carriage House at Carrot Top Cottage
A two-story house with a front porch, a white picket fence, and a driveway.

16. Cozy Riverfront Cottage, Fire Pit, Pet Friendly

Cozy Riverfront Cottage, Fire Pit, Pet Friendly
Rileyville
$318 nightly
The price is $354
Nov 16 - Nov 17
Total with taxes and fees
Cozy Riverfront Cottage, Fire Pit, Pet Friendly
A wooden deck with a glass railing overlooking a forested area.

17. Round House w Mountain View Hot Tub

Round House w Mountain View Hot Tub
Luray
10.0 out of 10, Exceptional, (1 review)
$255 nightly
The price is $282
Nov 16 - Nov 17
Total with taxes and fees
Round House w Mountain View Hot Tub
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.
$379 nightly
The price is $423
Nov 29 - Nov 30
Total with taxes and fees
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
A white building with a red roof and a chimney, surrounded by trees and grassy area.

19. Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.6 out of 10, Exceptional, (17 reviews)
"We really enjoyed the secluded house surrounded by nature. The waterfall was smaller than we expected, but the sound of it was soothing and we enjoyed tubing in the pond. Our family appreciated the many games in the house and the ice-pops in the freezer."
United States
Dovid J.
$273 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure
Exterior

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
$447 nightly
The price is $499
Nov 16 - Nov 17
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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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 Theater.

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

Top reviews in Winchester

A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
Huntly

10/10 Excellent

Perfect
United States
Omar
Reviewed June 16, 2026
Glen Gordon Manor

Frequently Asked Questions

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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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