Compare Winchester Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Winchester

Briar Patch Bed & Breakfast Inn
23130 Briar Patch Ln Middleburg VA
Free Cancellation
Reserve now, pay when you stay
$275 nightly
The price is $314 total per night
$314 total
Jan 4 - Jan 5
Total with taxes and fees
Guests of Briar Patch Bed & Breakfast Inn enjoy free WiFi in public areas, a hot tub, and a seasonal outdoor pool. A stay here includes free parking. This guesthouse also has barbecue grills.
Pool
Hot Tub

White Moose Inn
291 Main St Washington VA
$339 nightly
The price is $366 total per night
$366 total
Jan 22 - Jan 23
Total with taxes and fees
White Moose Inn features free WiFi in public areas, free use of bicycles, and a computer station. You can put free parking to good use if you drive. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this golf guesthouse include a terrace, a garden, and wedding services.
Breakfast included
Parking included

The Bluebird Suite at Harpers Ferry Guest House
Harpers Ferry WV
$170 nightly
The price is $189 total per night
$189 total
Jan 5 - Jan 6
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Free WiFi
Air conditioning

►New! Unique Custom Crafted Train Station Lodge W/ private walking trails
Martinsburg WV
$243 nightly
The price is $270 total per night
$270 total
Jan 6 - Jan 7
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has barbecue grills.
Free WiFi
Air conditioning

The Goldfinch Suite at Harpers Ferry Guest House
Harpers Ferry WV
$170 nightly
The price is $189 total per night
$189 total
Jan 4 - Jan 5
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
Air conditioning
Parking available

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains VA
$376 nightly
The price is $403 total per night
$403 total
Jan 12 - Jan 13
Total with taxes and fees
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Free WiFi
Air conditioning

The Cardinal Suite at Harpers Ferry Guest House
Harpers Ferry WV
$180 nightly
The price is $201 total per night
$201 total
Jan 4 - Jan 5
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
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.
Hotel Options in Winchester

Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
$79 nightly
The price is $86 total per night from Jan 11 to Jan 12
$86 total
Jan 11 - Jan 12
Total with taxes and fees
9/10 Wonderful! (1,415 reviews)

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$99 nightly
The price is $107 total per night from Jan 5 to Jan 6
$107 total
Jan 5 - Jan 6
Total with taxes and fees
9.2/10 Wonderful! (2,241 reviews)

Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Jan 18 to Jan 19
$74 total
Jan 18 - Jan 19
Total with taxes and fees
8.4/10 Very Good! (1,081 reviews)
Winchester Guest Houses essential information
Accommodation | 19 Guest Houses |
|---|---|
Lowest Price | $74 |
Highest Price | $403 |
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 |
More to Explore
- Farmstay in White Post
- B&B in White Post
- Cabin Rentals in White Post
- Inns in White Post
- Hotels near Old Court House Civil War Museum
- Boutique Hotels in Winchester Historic District
- Cheap Hotels in Winchester Historic District
- Kid Friendly Hotels in Winchester Historic District
- Hotels with Pool in Winchester Historic District
- Luxury Hotels in Winchester Historic District
- Spa Resorts & in Winchester Historic District
- Winchester Historic District Hotels
- Hotels near The Kernstown Battlefield
- Hotels near Rocking S Ranch
- 3 Star Hotels in Boyce
- Farmstay in Boyce
- B&B in Boyce
- Cabin Rentals in Boyce
- Cottages in Boyce
- Boyce Hotels
- Motels in Boyce
- Villas in Boyce
- Hotels near Bright Box Theater
- Hotels near Handley Regional Library
- Gore Hotels
- Farmstay in Berryville
- B&B in Berryville
- Cabin Rentals in Berryville
- Chalets in Berryville
- Cottages in Berryville
- Extended Stay Hotels in Berryville
- Guest Houses in Berryville
- Gay Friendly Hotels in Berryville
- Hotels with Pool in Berryville
- Pet Friendly Hotels in Berryville
- Romantic Getaways & Hotels in Berryville
- Berryville Hotels
- Inns in Berryville
- Motels in Berryville
- Vacation Homes in Berryville
- Resorts in Berryville
- Hotels near Patsy Cline Historic House
- Apartments in Jordan Springs
- 3 Star Hotels in Old Town Winchester
- 4 Star Hotels in Old Town Winchester
- Boutique Hotels in Old Town Winchester
- Hotels with Balconies in Old Town Winchester
- Hotels with Bar in Old Town Winchester
- Hotels with Hot Tubs in Old Town Winchester
- Hotels with an Indoor Pool in Old Town Winchester
- Romantic Getaways & Hotels in Old Town Winchester
- Spa Resorts & in Old Town Winchester
- Old Town Winchester Hotels
- Hotels near Appleland Sports Center
- Hotels near Nalls Farm Market
- Hotels near Dinosaur Land
- Millwood Hotels
- Hotels near Winchester Medical Center
- Hotels near Museum of the Shenandoah Valley
- Apartments in Canterburg
- Hotels near Valerie Hill Winery
- Cross Junction Hotels
- Hotels near Shenandoah University
- Hotels near The Fire House Gallery
- Hotels near George Washington's Office
- Hotels near Mt Hebron Cemetery
- Hotels near Apple Blossom Mall
- Hotels near Rock Harbor Golf Course
- 4 Star Hotels in Stephenson
- 5 Star Hotels in Clear Brook
- Farmstay in Stephens City
- B&B in Stephens City
- Cabin Rentals in Stephens City
- Chalets in Stephens City
- Cottages in Stephens City
- Cheap Hotels in Stephens City
- Hotels with Hot Tubs in Stephens City
- Hotels with Restaurants in Stephens City
- Hotels with a Wedding Venue in Stephens City
- Winery Hotels in Stephens City
- Stephens City Hotels
- Motels in Stephens City
- Vacation Homes in Stephens City
- Hotels near Shenandoah Valley Discovery Museum
- Hotels near State Arboretum of Virginia


