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Featured Cottages in Winchester

Riversong Luxe Cabin w/ Fire Pit on North River
Private kitchen
Riversong Luxe Cabin w/ Fire Pit on North River
3.0 star property
Riversong Luxe Cabin w/ Fire Pit on North River
Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns
Dining
Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns
3.0 star property
10.0 out of 10, Exceptional, (1)
Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns
Charming Home With Yard Near Shenandoah River!
Private kitchen
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!
Renovated WV Schoolhouse: History Buffs Heaven!
Exterior
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!
Homey Luray Cabin w/ Fire Pit & Deck!
Microwave, oven, stovetop, dishwasher
Homey Luray Cabin w/ Fire Pit & Deck!
3.0 star property
Homey Luray Cabin w/ Fire Pit & Deck!
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
Property grounds
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
2.0 star property
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
Chic Front Royal Retreat Near Shenandoah River!
Terrace/patio
Chic Front Royal Retreat Near Shenandoah River!
3.0 star property
10.0 out of 10, Exceptional, (4)
"This was a lovely trip because of the home we stayed in. It had a wonderful ambiance and was clean. Thank you for having it available!"
Chic Front Royal Retreat Near Shenandoah River!
Historical Paris Cabin on Farm w/ Fire Pit!
Interior
Historical Paris Cabin on Farm w/ Fire Pit!
3.0 star property
Historical Paris Cabin on Farm w/ Fire Pit!
Lovettsville Cottage in Heart of Wine Country
Private kitchen
Lovettsville Cottage in Heart of Wine Country
3.0 star property
Lovettsville Cottage in Heart of Wine Country
Charming Hedgesville Retreat w/ Deck + Fireplace!
TV, fireplace
Charming Hedgesville Retreat w/ Deck + Fireplace!
3.0 star property
10.0 out of 10, Exceptional, (1)
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!
Harpers Ferry Cabin - Walk to Private Lake!
Outdoor dining
Harpers Ferry Cabin - Walk to Private Lake!
3.0 star property
Harpers Ferry Cabin - Walk to Private Lake!
Lush, Modern Farmhouse w/ Mtn Views & Sunroom
Private kitchen
Lush, Modern Farmhouse w/ Mtn Views & Sunroom
3.0 star property
Lush, Modern Farmhouse w/ Mtn Views & Sunroom
Creekside Berkeley Springs Cabin on 35 Acres!
Private kitchen
Creekside Berkeley Springs Cabin on 35 Acres!
3.0 star property
Creekside Berkeley Springs Cabin on 35 Acres!
Garnerland in Luray Pet-friendly Cabin w/ Porch
Outdoor dining
Garnerland in Luray Pet-friendly Cabin w/ Porch
3.0 star property
Garnerland in Luray Pet-friendly Cabin w/ Porch
Spacious Virginia Retreat w/ Deck & Scenic Views!
Interior
Spacious Virginia Retreat w/ Deck & Scenic Views!
3.0 star property
10.0 out of 10, Exceptional, (1)
"So I had to book a place big enough for a large family last minute and found this property and let me tell you this property was spacious and breathtaking! Had a everything we needed for a home away from home! The fridge and stove were a dream! The plus was having washer/dryer access, hot tub and a massage chair! Oh and the tower!! The view from the deck was beautiful but from the tower was just amazing! Will definitely be coming back especially once the pool is built!"
Spacious Virginia Retreat w/ Deck & Scenic Views!
Peaceful & Secluded Knoxville Retreat w/ Deck
Terrace/patio
Peaceful & Secluded Knoxville Retreat w/ Deck
3.0 star property
10.0 out of 10, Exceptional, (1)
"loved this property, secluded, quiet. Had everything we needed, coffee makers, utensils, washer/dryer, outdoor fire pit, to name a few. a couple of miles of the main road, but very scenic. Only negative, (and wasn't really a negative), the road to Harpers Ferry was out, had to use detour, and extra 20 minute drive, but was a beautiful detour drive!"
Peaceful & Secluded Knoxville Retreat w/ Deck
Pet-friendly Basye Vacation Rental w/ Fireplace!
Property grounds
Pet-friendly Basye Vacation Rental w/ Fireplace!
3.0 star property
10.0 out of 10, Exceptional, (3)
"The house was perfect! It was exactly as described. Sparkling clean, comfortable beds and linens. Lots of extras that made our stay comfy like game boards, puzzles, snacks, coffee and creamer. Thank you for sharing your beautiful home. "
Pet-friendly Basye Vacation Rental w/ Fireplace!
Couples Cabin - 5 Mi to DT Berkeley Springs!
1 bedroom, bed sheets
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!
Sunny Front Royal Vacation Rental w/ Hot Tub!
Terrace/patio
Sunny Front Royal Vacation Rental w/ Hot Tub!
3.0 star property
Sunny Front Royal Vacation Rental w/ Hot Tub!
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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Other property types in Winchester

Family Farmhouse Inn
Garden
Family Farmhouse Inn
3.0 star property
9.6 out of 10, Exceptional, (32)
"Very nice management "
The price is S$194
includes taxes & fees
3 Dec - 4 Dec
Family Farmhouse Inn
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Why book your cottage in Winchester with Expedia?
Expedia has some great cottages in Winchester, so get set for a memorable stay close to nature. If you need to stick to a budget, click on how much you want to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with free WiFi or a pool. We’ll help you find the right digs whatever your plans or bank balance.
How can I find cheap cottages in Winchester?
Expedia can help you locate cheap cottages in Winchester. To reserve a fantastic stay in a matter of clicks, try out our handy filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Winchester near my cottage?
You’ll find tons of fantastic things to sink your teeth into in Winchester. You won’t want to miss attractions like Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre. Winchester Little Theatre, Shenandoah University and Jim Barnett Park are other must-see’s.