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Compare Vacation Homes in Winchester with updated reviews, rates, and availability.

Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
9.8 out of 10, Exceptional, (197)

Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
9.8 out of 10, Exceptional, (91)

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (214)

Trailside Retreat in breathtaking Western Loudoun
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (44)

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
9.8 out of 10, Exceptional, (123)

Secluded River Cabin Getaway (Masten Cabin)
Secluded River Cabin Getaway (Masten Cabin)
9.8 out of 10, Exceptional, (143)

1805 Farmhouse with Heated Pool in Harpers Ferry
1805 Farmhouse with Heated Pool in Harpers Ferry
10.0 out of 10, Exceptional, (37)

Riverfront Retreat
Riverfront Retreat
10.0 out of 10, Exceptional, (27)
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

Star view cabin-Riverfront
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (306)

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.6 out of 10, Exceptional, (342)

Heaven's Hideaway- a perfect getaway near the Shenandoah River!
Heaven's Hideaway- a perfect getaway near the Shenandoah River!
9.6 out of 10, Exceptional, (100)
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.
Recent reviews of Winchester hotels
Recent reviews of Winchester hotels

Microtel Inn & Suites by Wyndham Winchester
5/5 Excellent
"Last minute decision to stay here and the front desk was so very nice. She explained everything we would need."
A verified traveler stayed at Microtel Inn & Suites by Wyndham Winchester
Posted 22 hours ago