Book Guest Houses in Winchester
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Featured Guest Houses in Winchester
Briar Patch Bed & Breakfast Inn
23130 Briar Patch Ln Middleburg VA
Free cancellation
Reserve now, pay when you stay
Stay at this guesthouse in Middleburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cana Vineyards and Winery and Aldie Mill Historic Park are located nearby.
Pool
Hot tub
White Moose Inn
291 Main St Washington VA
Book a stay at this golf guesthouse in Washington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions R.H. Ballard Shop & Gallery and Little Washington Theatre are located nearby.
Breakfast included
Parking included
The Bluebird Suite at Harpers Ferry Guest House
Harpers Ferry WV
The price is CA $172 per night
CA $172
CA $260 total
Jan 22 - Jan 23, 2026
includes taxes & fees
Stay at this guesthouse in Harpers Ferry. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the clean rooms in our reviews. Popular attractions Harpers Ferry Children's Park and Virginius Island are located nearby.
Free WiFi
Air conditioning
►New! Unique Custom Crafted Train Station Lodge W/ private walking trails
Martinsburg WV
The price is CA $130 per night
CA $130
CA $371 total
Dec 24 - Dec 25
includes taxes & fees
Stay at this guesthouse in Martinsburg. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions A-T Gift Company Farm Winery and Chesapeake and Ohio Canal are located nearby.
Free WiFi
Air conditioning
The Goldfinch Suite at Harpers Ferry Guest House
Harpers Ferry WV
The price is CA $172 per night
CA $172
CA $260 total
Jan 22 - Jan 23, 2026
includes taxes & fees
Stay at this guesthouse in Harpers Ferry. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Harpers Ferry Children's Park and Virginius Island are located nearby.
Air conditioning
Parking available
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains VA
The price is CA $378 per night
CA $378
CA $598 total
Jan 22 - Jan 23, 2026
includes taxes & fees
Stay at this guesthouse in Marshall. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Great Meadow and Marshall Center are located nearby.
Free WiFi
Air conditioning
The Cardinal Suite at Harpers Ferry Guest House
Harpers Ferry WV
The price is CA $186 per night
CA $186
CA $276 total
Jan 22 - Jan 23, 2026
includes taxes & fees
Stay at this guesthouse in Harpers Ferry. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Harpers Ferry Children's Park and Virginius Island are located nearby.
Free WiFi
Air conditioning
The Chickadee Room at Harpers Ferry Guest House
Harpers Ferry WV
The price is CA $150 per night
CA $150
CA $236 total
Jan 22 - Jan 23, 2026
includes taxes & fees
Stay at this guesthouse in Harpers Ferry. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Harpers Ferry Children's Park and Virginius Island are located nearby.
Air conditioning
Parking available
Riverview Suite at La Soledad
Harpers Ferry WV
The price is CA $455 per night
CA $455
CA $643 total
Dec 24 - Dec 25
includes taxes & fees
Stay at this guesthouse in Harpers Ferry. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Hollywood Casino at Charles Town Races and Harpers Ferry Children's Park are located nearby.
Air conditioning
Parking available
Guest House at Mt Independence
Delaplane VA
Stay at this guesthouse in Delaplane. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Delaplane Cellars and RdV Vineyards are located nearby.
Pet-friendly
Free WiFi
Riverfront Oasis with Mountain Views, close to town
Middletown VA
Stay at this guesthouse in Middletown. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Jackson's Chase Golf Course and Shenandoah River are located nearby.
Free WiFi
Air conditioning
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.
Top trending hotels in Winchester
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
The price is CA $133 per night from Jan 5 to Jan 6
CA $133
CA $145 total
Jan 5 - Jan 6, 2026
includes taxes & fees
9.4/10 Exceptional! (1,086 reviews)
Winchester Guest Houses essential information
Accommodation | 19 Guest Houses |
|---|---|
Lowest Price | CA $102 |
Highest Price | CA $643 |
Popular accommodation | Briar Patch Bed & Breakfast Inn, White Moose Inn, The Bluebird Suite at Harpers Ferry Guest House, ►New! Unique Custom Crafted Train Station Lodge W/ private walking trails, The Goldfinch Suite at Harpers Ferry Guest House, Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment, The Cardinal Suite at Harpers Ferry Guest House, The Chickadee Room at Harpers Ferry Guest House, Riverview Suite at La Soledad, Guest House at Mt Independence, Riverfront Oasis with Mountain Views, close to town , Guest House at Mt. Independence |