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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in Winchester

Riversong Cabin w/ Fire Pit on North River
Interior

Riversong Cabin w/ Fire Pit on North River

3.0 star property
Riversong Cabin w/ Fire Pit on North River
Walk to Stores: Home in Historic Shepherdstown!
Interior

Walk to Stores: Home in Historic Shepherdstown!

3.0 star property
Walk to Stores: Home in Historic Shepherdstown!
Charming Home With Yard Near Shenandoah River!
Front of property

Charming Home With Yard Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy house nestled in the mountains of West Virginia. Well-maintained, clean, great yard for pets and/or kids! Lovely grilling and fire pit area. We throughly enjoyed our stay!"
Charming Home With Yard Near Shenandoah River!
Chic Front Royal Retreat Near Shenandoah River!
Interior

Chic Front Royal Retreat Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (5)
"Nice place near skyline drive"
Chic Front Royal Retreat Near Shenandoah River!
Peaceful Luray Cabin w/ Hot Tub, Deck & Fire Pit!
Interior

Peaceful Luray Cabin w/ Hot Tub, Deck & Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Luray Cabin w/ Hot Tub, Deck & Fire Pit!
Secluded Berkeley Springs Home w/ Fire Pit + Deck!
Interior

Secluded Berkeley Springs Home w/ Fire Pit + Deck!

3.0 star property
Secluded Berkeley Springs Home w/ Fire Pit + Deck!
Charming Hedgesville Retreat w/ Deck + Fireplace!
TV, fireplace

Charming Hedgesville Retreat w/ Deck + Fireplace!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We wanted a quiet getaway and that’s exactly what we got. We like Hedgesville’s proximity to Berkeley Springs, Harpers Ferry and Winchester, VA. Hedgesville itself doesn’t have a lot going on - a few independent restaurants & shops, a Martin’s grocery store. If you’re looking for Walmart or chain restaurants, there are plenty in nearby Martinsburg. This visit for us, though, was all about staying in and enjoying the woods around us. While there are half a dozen or so homes around the cabin,...
Charming Hedgesville Retreat w/ Deck + Fireplace!
Front Royal Retreat ~ 1 Mi to National Park!
Private kitchen

Front Royal Retreat ~ 1 Mi to National Park!

3.0 star property
Front Royal Retreat ~ 1 Mi to National Park!
Sunny Front Royal Vacation Rental w/ Hot Tub!
Dining

Sunny Front Royal Vacation Rental w/ Hot Tub!

3.0 star property
Sunny Front Royal Vacation Rental w/ Hot Tub!
Mountain Town Adventures Home w/ Fire Pit!
Interior

Mountain Town Adventures Home w/ Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was fantastic"
Mountain Town Adventures Home w/ Fire Pit!
Spacious Virginia Vacation Rental w/ Yard & Sauna
Interior

Spacious Virginia Vacation Rental w/ Yard & Sauna

3.0 star property
Spacious Virginia Vacation Rental w/ Yard & Sauna
Modern Mountain Retreat w/ Deck + Hot Tub!
Private kitchen

Modern Mountain Retreat w/ Deck + Hot Tub!

3.0 star property
Modern Mountain Retreat w/ Deck + Hot Tub!
Renovated WV Schoolhouse: History Buffs Heaven!
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Renovated WV Schoolhouse: History Buffs Heaven!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The school house is amazing. Clean, comfortable, quiet. I would definitely stay there again if I am in the area"
Renovated WV Schoolhouse: History Buffs Heaven!
Cozy Winter Retreat: Great Location & Pet Friendly
Interior

Cozy Winter Retreat: Great Location & Pet Friendly

3.0 star property
10.0 out of 10, Exceptional, (1)
Cozy Winter Retreat: Great Location & Pet Friendly
Couples Cabin - 5 Mi to DT Berkeley Springs!
Interior

Couples Cabin - 5 Mi to DT Berkeley Springs!

3.0 star property
8.0 out of 10, Very good, (1)
"The people were super friendly... the place is very nice. "
Couples Cabin - 5 Mi to DT Berkeley Springs!
Cozy Cabin With Sunroom & Cacapon River Access!
TV, fireplace

Cozy Cabin With Sunroom & Cacapon River Access!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic family trip. This was a great landing point to amazing outdoor adventures in the area. "
Cozy Cabin With Sunroom & Cacapon River Access!
Front Royal Hilltop Cabin w/ Panoramic Views!
Outdoor spa tub

Front Royal Hilltop Cabin w/ Panoramic Views!

3.0 star property
Front Royal Hilltop Cabin w/ Panoramic Views!
Warrenton Gem: Walk to Downtown!
Books

Warrenton Gem: Walk to Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"A very nice practical house for a group of 6-7. Clean & cheerful with a nice layout. Our family was here for a wedding, so there was a wide age range, and we all had a good gathering area, as well as some privacy with the upstairs bedrooms. The futon couch wasn't very comfortable to sit on & an end table between the couches would have been nice. But it had everything we really nice. Thank you!"
Warrenton Gem: Walk to Downtown!
Homey Luray Cabin w/ Fire Pit & Deck!
Front of property

Homey Luray Cabin w/ Fire Pit & Deck!

3.0 star property
9.0 out of 10, Wonderful, (2)
"The downstairs area would not get warm enough to stay downstairs, the wood for the back porch was rotting too underneath so we stayed off that, and I’m not sure if it was someone who stayed before left a box of beer by the jacuzzi. Overall we had a good time. "
Homey Luray Cabin w/ Fire Pit & Deck!
Lush, Modern Farmhouse w/ Mtn Views & Sunroom
Interior

Lush, Modern Farmhouse w/ Mtn Views & Sunroom

3.0 star property
Lush, Modern Farmhouse w/ Mtn Views & Sunroom
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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Frequently asked questions

Why book your cottage in Winchester with Expedia?
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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.