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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winchester cottages

Terrace/patio

1. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.6 out of 10, Exceptional, (15 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is £371
includes taxes & fees
3 Sept - 4 Sept
Mountain View Cottage | Hot Tub & Game Room
Outdoor spa tub

2. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.8 out of 10, Exceptional, (37 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is £387
includes taxes & fees
3 Sept - 4 Sept
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Exterior

3. 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.
The price is £169
includes taxes & fees
9 Sept - 10 Sept
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Terrace/patio

4. Mountain-View Cottage | Hot Tub & River Views

Mountain-View Cottage | Hot Tub & River Views
Front Royal
The price is £402
includes taxes & fees
14 Sept - 15 Sept
Mountain-View Cottage | Hot Tub & River Views
Exterior

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 £191
includes taxes & fees
7 Sept - 8 Sept
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Outdoor spa tub

6. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (15 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is £321
includes taxes & fees
3 Sept - 4 Sept
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

7. The VUE | Mountaintop 4BR | Hot Tub & Views

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (25 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.
The price is £490
includes taxes & fees
14 Sept - 15 Sept
The VUE | Mountaintop 4BR | Hot Tub & Views
Exterior

8. 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, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
Woodsy Retreat with a Hot Tub and Seasonal Views!
Outdoor spa tub

9. 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, (26 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveller
The price is £283
includes taxes & fees
14 Sept - 15 Sept
Cottage w/ Hot Tub and 100-Mile Valley Views!
Dining

10. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is £163
includes taxes & fees
6 Sept - 7 Sept
Quaint Mini Cottage in Shepherdstown - Walking Distance
Terrace/patio

11. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (39 reviews)
"Excellent property for a relaxing getaway. Very clean. Host very responsive."
United States
Brad C.
The price is £380
includes taxes & fees
8 Sept - 9 Sept
Peaceful Lakefront Cottage with Mountain Views!
Outdoor dining

12. 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.
The price is £360
includes taxes & fees
21 Sept - 22 Sept
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Room

13. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (52 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is £152
includes taxes & fees
10 Sept - 11 Sept
The Carriage House at Carrot Top 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, (64 reviews)
"Loved out stay! "
United States
Emilee
The price is £294
includes taxes & fees
3 Sept - 4 Sept
18th Century Stone Cottage minutes from historic Middleburg
Exterior

15. 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.
The price is £233
includes taxes & fees
8 Sept - 9 Sept
Peaceful Waterfall House -- 2 bedroom hidden treasure
Exterior

16. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (31 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 £273
includes taxes & fees
3 Sept - 4 Sept
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Outdoor dining

17. Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room

Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room
Berkeley Springs
10.0 out of 10, Exceptional, (3 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 £292
includes taxes & fees
7 Sept - 8 Sept
Country Road Cottage-Mountain Views + Private Hot Tub + Sauna + Game Room
Terrace/patio

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, (24 reviews)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
The price is £292
includes taxes & fees
6 Sept - 7 Sept
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

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

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (106 reviews)
"Place was very clean and well equipped."
United States
Suze F.
The price is £239
includes taxes & fees
8 Sept - 9 Sept
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
House (2 Bedrooms) | Interior

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 £247
includes taxes & fees
8 Sept - 9 Sept
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.
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Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Excellent"
Marian 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
506
Accommodation
194 Cottages
Lowest Price
£152
Highest Price
£490

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 Harbour 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.