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Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
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Apr 25 - Apr 27
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May 23 - May 25

Compare 89 Cottages in Winchester with updated reviews, rates, and availability.

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, (5)
"Nice place near skyline drive"
Chic Front Royal Retreat Near Shenandoah River!
Riversong Luxe Cabin w/ Fire Pit on North River
House (3 Bedrooms) | Interior

Riversong Luxe Cabin w/ Fire Pit on North River

3.0 star property
Riversong Luxe Cabin w/ Fire Pit on North River
Homey Luray Cabin w/ Fire Pit & Deck!
Interior

Homey Luray Cabin w/ Fire Pit & Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed Luray Caverns during our stay in Shenandoah. This hotel is very clean and has cute, very comfortable furniture. The place is great and the hosts are lovely and communicate quickly."
Homey Luray Cabin w/ Fire Pit & Deck!
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!
Charming Home With Yard Near Shenandoah River!
House (3 Bedrooms) | Interior

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

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

3.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Luray Cabin w/ Hot Tub, Deck & Fire Pit!
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!
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!
Lovettsville Cottage in Heart of Wine Country
Cottage (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, dishwasher

Lovettsville Cottage in Heart of Wine Country

3.0 star property
Lovettsville Cottage in Heart of Wine Country
Wardensville Cabin w/ Hot Tub, Creek & Fire Pit!
Interior

Wardensville Cabin w/ Hot Tub, Creek & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great stay at the cabin! The kitchen is well stocked with everything you need to cook at home but we would recommend bringing some groceries. The house was clean and inviting and offered lots of privacy. There was no cell service but the Wi-Fi was great. We’d love to return!"
Wardensville Cabin w/ Hot Tub, Creek & Fire Pit!
Pet-friendly Basye Vacation Rental w/ Fireplace!
Interior

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!
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!
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
Interior

Cozy Virginia Escape w/ Deck, Grill & Fire Pit!

2.0 star property
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
Front Royal Retreat ~ 1 Mi to National Park!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Front Royal Retreat ~ 1 Mi to National Park!

3.0 star property
Front Royal Retreat ~ 1 Mi to National Park!
Couples Cabin - 5 Mi to DT Berkeley Springs!
House (1 Bedroom) | 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!
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Interior

Home w/ Hot Tub Near Shenandoah Nat'l Park!

3.0 star property
Home w/ Hot Tub Near Shenandoah Nat'l Park!
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!
Bright Bluemont Home w/ On-site Pond & Mtn Views!
Microwave, oven, stovetop, dishwasher

Bright Bluemont Home w/ On-site Pond & Mtn Views!

3.0 star property
Bright Bluemont Home w/ On-site Pond & Mtn Views!
Creekside Berkeley Springs Cabin on 35 Acres!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Creekside Berkeley Springs Cabin on 35 Acres!

3.0 star property
Creekside Berkeley Springs Cabin on 35 Acres!
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!
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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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 Harbor 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.