A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Our top choices for Winchester cottages

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 AED 545
AED 784 total
includes taxes & fees
17 Nov - 18 Nov
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

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.
Mountaintop Cottage | Private Hot Tub

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
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

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.
Mountain View Cottage | Hot Tub & Game Room

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

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.
Mountain View Cottage with Hot Tub and River Views

7. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (26 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 AED 441
AED 774 total
includes taxes & fees
8 Nov - 9 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance

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 AED 367
AED 1,619 total
includes taxes & fees
18 Nov - 19 Nov
Peaceful Lakefront Cottage with Mountain Views!

9. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is AED 444
AED 1,305 total
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!

10. 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 AED 444
AED 1,804 total
includes taxes & fees
18 Nov - 19 Nov
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

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 AED 367
AED 1,492 total
includes taxes & fees
19 Nov - 20 Nov
Woodsy Retreat with a Hot Tub and Seasonal Views!

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 AED 441
AED 1,608 total
includes taxes & fees
16 Nov - 17 Nov
Cottage w/ Hot Tub and 100-Mile Valley Views!

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 AED 511
AED 776 total
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage

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 AED 476
AED 1,051 total
includes taxes & fees
9 Nov - 10 Nov
Round House w Mountain View Hot Tub

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
The price is AED 1,572
AED 1,905 total
includes taxes & fees
4 Nov - 5 Nov
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia

16. 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 AED 1,065
AED 1,450 total
includes taxes & fees
15 Nov - 16 Nov
18th Century Stone Cottage minutes from historic Middleburg

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.
The price is AED 622
AED 1,542 total
includes taxes & fees
4 Nov - 5 Nov
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage

18. 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 AED 737
AED 1,109 total
includes taxes & fees
8 Nov - 9 Nov
Peaceful Waterfall House -- 2 bedroom hidden treasure

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
The price is AED 643
AED 1,207 total
includes taxes & fees
4 Nov - 5 Nov
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

20. 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 AED 715
AED 1,149 total
includes taxes & fees
4 Nov - 5 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
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

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