Monthly Vacation Rentals, Apartment, House in Winchester, VA

Compare 384 available vacation home properties, starts from $26

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ACCOMMODATION TYPES

Cheap Monthly Vacation Rentals in Winchester, VA: Top Deals

Relax Inn Front Royal
Relax Inn Front Royal
Relax Inn Front Royal
Relax Inn Front Royal
8.2 (37 reviews)
Relax Inn Front Royal
Hotel · 2 Guests · 1 Bedroom
$64 /night
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Red Roof Inn Martinsburg
Red Roof Inn Martinsburg
Red Roof Inn Martinsburg
Red Roof Inn Martinsburg
5.8 (155 reviews)
Red Roof Inn Martinsburg
Motel · 2 Guests · 1 Bedroom
$70 /night
View deal
Red Roof Inn Winchester, VA
Red Roof Inn Winchester, VA
Red Roof Inn Winchester, VA
Red Roof Inn Winchester, VA
Red Roof Inn Winchester, VA
Motel · 2 Guests · 1 Bedroom
$62 /night
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Quality Inn
Quality Inn
Quality Inn
Quality Inn
8.7 (190 reviews)
Quality Inn
Hotel · 2 Guests · 1 Bedroom
$78 /night
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Serenity Apt in DT Charles Town near Harpers Ferry
Serenity Apt in DT Charles Town near Harpers Ferry
Serenity Apt in DT Charles Town near Harpers Ferry
Serenity Apt in DT Charles Town near Harpers Ferry
9.6 (17 reviews)
Serenity Apt in DT Charles Town near Harpers Ferry
Apartment · 2 Guests · 1 Bedroom
$83 /night*
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Quality Suites Martinsburg
Quality Suites Martinsburg
Quality Suites Martinsburg
Quality Suites Martinsburg
6.8 (165 reviews)
Quality Suites Martinsburg
Hotel · 2 Guests · 1 Bedroom
$70 /night
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Quality Inn
Quality Inn
Quality Inn
Quality Inn
8.6 (291 reviews)
Quality Inn
Hotel · 2 Guests · 1 Bedroom
$101 /night
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Comfort Inn & Suites
Comfort Inn & Suites
Comfort Inn & Suites
Comfort Inn & Suites
9.3 (239 reviews)
Comfort Inn & Suites
Hotel · 2 Guests · 1 Bedroom
$100 /night
View deal
Holiday Inn Martinsburg, an IHG Hotel
Holiday Inn Martinsburg, an IHG Hotel
Holiday Inn Martinsburg, an IHG Hotel
Holiday Inn Martinsburg, an IHG Hotel
9.0 (175 reviews)
Holiday Inn Martinsburg, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$106 /night
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The Inn at Charles Town / Hollywood Casino
The Inn at Charles Town / Hollywood Casino
The Inn at Charles Town / Hollywood Casino
The Inn at Charles Town / Hollywood Casino
8.4 (218 reviews)
The Inn at Charles Town / Hollywood Casino
Hotel · 2 Guests · 1 Bedroom
$92 /night
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Travelodge by Wyndham Charles Town - Harpers Ferry
Travelodge by Wyndham Charles Town - Harpers Ferry
Travelodge by Wyndham Charles Town - Harpers Ferry
Travelodge by Wyndham Charles Town - Harpers Ferry
6.0 (6 reviews)
Travelodge by Wyndham Charles Town - Harpers Ferry
Hotel · 2 Guests · 1 Bedroom
$63 /night
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Holiday Inn Winchester Southeast-Historic Gateway, an IHG Hotel
Holiday Inn Winchester Southeast-Historic Gateway, an IHG Hotel
Holiday Inn Winchester Southeast-Historic Gateway, an IHG Hotel
Holiday Inn Winchester Southeast-Historic Gateway, an IHG Hotel
8.8 (416 reviews)
Holiday Inn Winchester Southeast-Historic Gateway, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$89 /night
View deal
The Getaway that's Just Far Enough
The Getaway that's Just Far Enough
The Getaway that's Just Far Enough
The Getaway that's Just Far Enough
9.6 (84 reviews)
The Getaway that's Just Far Enough
Holiday home · 2 Guests · 1 Bedroom
$95 /night*
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Wayside Inn
Wayside Inn
Wayside Inn
Wayside Inn
9.2 (320 reviews)
Wayside Inn
Hotel · 2 Guests · 1 Bedroom
$85 /night
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The Sunshine APT in DT Charles Town near Harpers Ferry
The Sunshine APT in DT Charles Town near Harpers Ferry
The Sunshine APT in DT Charles Town near Harpers Ferry
The Sunshine APT in DT Charles Town near Harpers Ferry
9.4 (21 reviews)
The Sunshine APT in DT Charles Town near Harpers Ferry
Holiday home · 2 Guests · 1 Bedroom
$82 /night*
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Super 8 by Wyndham Winchester VA
Super 8 by Wyndham Winchester VA
Super 8 by Wyndham Winchester VA
Super 8 by Wyndham Winchester VA
Super 8 by Wyndham Winchester VA
Hotel · 2 Guests · 1 Bedroom
$60 /night
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Super 8 by Wyndham Martinsburg
Super 8 by Wyndham Martinsburg
Super 8 by Wyndham Martinsburg
Super 8 by Wyndham Martinsburg
5.6 (217 reviews)
Super 8 by Wyndham Martinsburg
Motel · 2 Guests · 1 Bedroom
$50 /night
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Sleep Inn & Suites
Sleep Inn & Suites
Sleep Inn & Suites
Sleep Inn & Suites
Sleep Inn & Suites
Hotel · 2 Guests · 1 Bedroom
$76 /night
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The Knolls
The Knolls
The Knolls
The Knolls
10 (16 reviews)
The Knolls
Motel · 2 Guests · 1 Bedroom
$100 /night
View deal
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
Hotel · 2 Guests · 1 Bedroom
$92 /night
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Similar Inspirational Vacation Rental Destinations

Monthly Apartment Rentals in Winchester, VA

2nd Floor, Efficiency, Private Entrance
2nd Floor, Efficiency, Private Entrance
2nd Floor, Efficiency, Private Entrance
2nd Floor, Efficiency, Private Entrance
2nd Floor, Efficiency, Private Entrance
2nd Floor, Efficiency, Private Entrance
5.0 (30 reviews)
2nd Floor, Efficiency, Private Entrance
Apartment · 2 Guests · 1 Bedroom
$85 /night*
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How Does The Vacation Home Rental Price Look Like in Winchester, VA?
Vacation House & Cabin Rental Price Information in Winchester, VA
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The graph shows the percentages of vacation homes in each price bucket. Winchester has the largest percentage (22.34%) of homes in $150 - $200 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
How Many Rental Accommodations Are Pets Friendly in Winchester, VA?
Percentage of Pet Friendly Rental Properties in Winchester, VA
+
43.23% of vacation homes in Winchester are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Is Winchester, VA a convenient place to live?
Convenience of Living in Winchester, VA
+

Winchester, VA is a great location for people looking for monthly rentals. The surrounding area has a low crime rate, and there are plenty of public transportation options such as buses, trains, and subways within a few miles of the city. There are also many amenities located nearby, such as grocery stores, pharmacies, restaurants, and other essential amenities that can be reached by walking or a short drive. Business centers and workplaces such as conference centers and co-working spaces are also close by. Healthcare facilities such as hospitals, clinics, and pharmacies are all easily accessible.

  • The Martinsburg Station: 2.9 miles away
  • Safeway Grocery Store: 0.8 miles away
  • Valley Health Urgent Care: 1.7 miles away
  • Old Town Commons: 1.3 miles away
Where Should We Visit in Winchester, VA Area?
Destinations To Visit During the Month in Winchester, VA
+

Other Vacation Rentals Ideas

Monthly Hotel Rentals in Winchester, VA

Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Rodeway Inn & Suites
Hotel
$68 /night
View deal
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
Hampton Inn and Suites Charles Town
4.6 (379 reviews)
Hampton Inn and Suites Charles Town
Hotel
$156 /night
View deal
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
Hampton Inn Martinsburg South Inwood
4.6 (177 reviews)
Hampton Inn Martinsburg South Inwood
Hotel
$114.01 /night
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Monthly House Rentals in Winchester, VA

Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
Cozy Lakeside Homestead
5.0 (60 reviews)
Cozy Lakeside Homestead
House · 6 Guests · 2 Bedrooms
$210 /night*
View deal
Ledge House Bed & Breakfast
Ledge House Bed & Breakfast
Ledge House Bed & Breakfast
Ledge House Bed & Breakfast
Ledge House Bed & Breakfast
4.8 (108 reviews)
Ledge House Bed & Breakfast
House
$145 /night
View deal
River House Near Harpers Ferry!
River House Near Harpers Ferry!
River House Near Harpers Ferry!
River House Near Harpers Ferry!
River House Near Harpers Ferry!
River House Near Harpers Ferry!
River House Near Harpers Ferry!
River House Near Harpers Ferry!
House
$999 /night
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Monthly Rentals with Kitchen in Winchester, VA

Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
Room In Central Historic Downtown - Appalachian
4.0 (2 reviews)
Room In Central Historic Downtown - Appalachian
Guest House · 2 Guests · 1 Bedroom
$145 /night*
View deal
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cozy Cabin Hidden Away on a Lake!
Cabin
$148 /night
View deal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Front Royal
4.7 (96 reviews)
TownePlace Suites by Marriott Front Royal
Hotel
$170 /night
View deal
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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