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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Winchester

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Exterior

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

10.0 out of 10, Exceptional, (68)
"Sweet l, well located property with everything you need for a stay! "
The price is NZ$536
includes taxes & fees
25 Aug - 26 Aug
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!
Exterior

Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

10.0 out of 10, Exceptional, (178)
"I loved my stay! The cottage was clean and cozy, and being able to use the hot tub was amazing. Ed and Betsy and all the animals were welcoming. The cottage was especially beautiful during sunrise. A very peaceful environment to stay in. "
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!
Secluded, Cozy Cottage in the Shenandoah Valley
Exterior

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (179)
"A real cute place with a cozy layout and amazing bathroom and shower. It was just secluded enough but not overly challenging to get to. The upper porch was great for hanging out and watching the pair of hummingbirds that seem to have made the area home. The bed was comfortable but also a little squeaky and noisy. We really enjoyed our stay and it was just the relaxing getaway we needed. "
Secluded, Cozy Cottage in the Shenandoah Valley
The Carriage House at Carrot Top Cottage
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (38)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is NZ$301
includes taxes & fees
18 Aug - 19 Aug
The Carriage House at Carrot Top Cottage
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Outdoor spa tub

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

9.8 out of 10, Exceptional, (28)
"So much to do in the area, cute little cottage, very clean and comfortable "
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (39)
"We had a great family trip here! Close to everything that Harper’s Ferry has to offer! Highly recommend this cute cabin for your trip!"
Carrot Top Cottage surrounded by National Park
Raspberry Retreat Cottage
Outdoor dining

Raspberry Retreat Cottage

Raspberry Retreat Cottage
Cozy Stone Cottage in Round Hill, VA
Exterior

Cozy Stone Cottage in Round Hill, VA

9.6 out of 10, Exceptional, (5)
"We had an excellent stay at cottage! It was perfect for a short weekend away with girlfriends. It was quaint and historic but didn't lack modern day comforts. Highly recommend for anyone looking for a few days away, with easy access to all Round Hill & Purcellville has to offer. "
Cozy Stone Cottage in Round Hill, VA
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (124)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Wild Hare Cottage
Terrace/patio

Wild Hare Cottage

10.0 out of 10, Exceptional, (6)
"We had just a quick overnight stay, the cottage is cozy, clean, and charming. Communication was easy and clear, we'd love to stay again!"
The price is NZ$401
includes taxes & fees
6 Aug - 7 Aug
Wild Hare Cottage
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

9.8 out of 10, Exceptional, (10)
"Good place for a nice quite weekend."
The price is NZ$598
includes taxes & fees
4 Aug - 5 Aug
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (15)
"Very nice property with convenient location! Within walking distance of down town. "
The price is NZ$545
includes taxes & fees
13 Aug - 14 Aug
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (19)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
The price is NZ$911
includes taxes & fees
6 Aug - 7 Aug
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Property grounds

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

9.8 out of 10, Exceptional, (6)
"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Lovettsville Cottage in Heart of Wine Country
Outdoor dining

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (34)
"We stayed here for a few days over the Thanksgiving holiday. It was cozy, comfortable, and had all the great comforts of a home away from home. "
Lovettsville Cottage in Heart of Wine Country
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
Exterior

Lost River Swiss Cottage/10 acres/Private Dog Park/Streams

9.8 out of 10, Exceptional, (129)
"Beautiful property Beautiful views It is located down gravel lane Nice beds living space"
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
Hunt Country cottage in Upperville!
Exterior

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay and look forward to booking again next year!"
Hunt Country cottage in Upperville!
A Restored Wagon Barn On A 1790's Farm.
Exterior

A Restored Wagon Barn On A 1790's Farm.

10.0 out of 10, Exceptional, (110)
"Great stay! Close to Appalachian Trail hiking (Bears Den and Ravens Rock), close to some great breweries and wineries, close to some wonderful restaurants...very peaceful setting with open floor plan on main level. Really enjoyed the time spent here."
A Restored Wagon Barn On A 1790's Farm.
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.6 out of 10, Exceptional, (30)
"The place is great! Clean, comfortable, close to downtown. The host was very responsive and friendly. "
The price is NZ$759
includes taxes & fees
4 Aug - 5 Aug
Royal Heritage Home @ Historic Leesburg
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
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
"Wonderful stay! Room layout was very different and very good. Nice place. nice people,"
SUSAN 1-night trip
Posted 20 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

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.