The Best Airbnb Deals in
Winchester, Virginia

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Winchester, Virginia. Enter your travel dates to find the best deals!

Search for a city
AirDNA Score: 93
$120/night

Downtowner

2 beds
1 bath
4 guests
Average Price:  
$124
3% Cheaper
than normal
AirDNA Score: 86
$285/night

Stone home in heart of downtown

2 beds
2.5 baths
7 guests
Average Price:  
$302
6% Cheaper
than normal
AirDNA Score: 79
$109/night

Emma''s Stone Cottage

2 beds
2 baths
4 guests
Average Price:  
$140
22% Cheaper
than normal
AirDNA Score: 79
$99/night

City Charmer minutes from Old Town

2 beds
1 bath
4 guests
Average Price:  
$140
29% Cheaper
than normal
AirDNA Score: 71
$70/night

Safe, cozy oasis with private living & bath.

1 bed
1 bath
3 guests
Average Price:  
$87
20% Cheaper
than normal
AirDNA Score: 71
$120/night

Pretty Little Apt by the Train II

1 bed
1 bath
2 guests
Average Price:  
$132
9% Cheaper
than normal
AirDNA Score: 67
$86/night

The Comfortable In-Towner

1 bed
1 bath
2 guests
Average Price:  
$90
4% Cheaper
than normal
AirDNA Score: 65
$135/night

Historic District Charm On Cameron Street

3 beds
1.5 baths
4 guests
Average Price:  
$167
19% Cheaper
than normal
AirDNA Score: 61
$108/night

Log house in Historic Winchester

1 bed
1 bath
4 guests
Average Price:  
$133
19% Cheaper
than normal
AirDNA Score: 59
$150/night

Majestic Mountain Cabin

2 beds
1 bath
4 guests
Average Price:  
$150
0% Cheaper
than normal
AirDNA Score: 50
$110/night

The Fairmont House

4 beds
2.5 baths
8 guests
Average Price:  
$217
49% Cheaper
than normal
AirDNA Score: 49
$120/night

The Birds Nest tiny house at Hedgebrook Farm

1 bed
1 bath
2 guests
Average Price:  
$120
0% Cheaper
than normal
AirDNA Score: 43
$72/night

Fairmont North

2 beds
1 bath
4 guests
Average Price:  
$119
39% Cheaper
than normal
AirDNA Score: 43
$135/night

Secret Gardens Guest House

1 bed
1 bath
2 guests
Average Price:  
$185
27% Cheaper
than normal
AirDNA Score: 36
$75/night

Fairmont South

2 beds
1.5 baths
4 guests
Average Price:  
$145
48% Cheaper
than normal