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Check prices for these dates

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8 Aug - 10 Aug
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15 Aug - 17 Aug
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29 Aug - 31 Aug
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26 Sept - 28 Sept

Featured Cottages in Winchester

Riversong Cabin w/ Fire Pit on North River
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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!
Enjoy meals in this stylish dining area with a round table and comfortable seating for four.

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!
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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!
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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!
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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!
Relax in this spacious room with a high ceiling, featuring a sliding glass door to an outdoor area, a dining table for four, and a cozy seating area with a sofa and side table.

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!
Relax in this inviting living room with a brick fireplace, comfortable seating, and a large sliding glass door leading to a deck with a tree-lined view.

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!
Enjoy cooking in this well-lit kitchen with a central island and essential appliances.

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!
Spacious room with a round dining table and unique spiral staircase.

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!
Cozy up by the fireplace and enjoy meals in the dining area with a view of the outdoor patio.

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
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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!
Kitchen features a dishwasher, oven, microwave, and sink with a window above.

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
Efficient kitchen with a gas stove, double oven, and stainless steel appliances.

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!
Relax in a cozy room with a four-poster bed, ceiling fan, and large window with shutters.

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!
Relax in a spacious room with a high ceiling, ceiling fan, and large window offering a view of the surrounding landscape.

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!
Relax in a serene hot tub surrounded by a natural landscape.

Front Royal Hilltop Cabin w/ Panoramic Views!

3.0 star property
Front Royal Hilltop Cabin w/ Panoramic Views!
Warrenton Gem: Walk to Downtown!
Relax in a spacious living area with a large flat-screen TV and comfortable seating.

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!
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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
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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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Top Winchester Hotel Reviews

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

10/10 Excellent
"quiet"
bernard 1-night trip
Posted 1 day ago
SpringHill Suites by Marriott Winchester

Frequently asked questions

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We think that holidays should be simple, so if you're in search of cottages in Winchester at a competitive price, Expedia has got your back. Keep costs down and check in to a cheap option far away from the city rush, or splurge on an upmarket cottage to spoil your favourite people.
How can I find cheap cottages in Winchester?
The easiest way to locate cheap cottages in Winchester is with Expedia's useful filter tool. Narrow your search results by star rating, amenities and budget to snag awesome prices in just a few keystrokes.
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.