Vacation Rentals in Winchester, VA

PRICE PER NIGHT

ACCOMMODATION TYPES

Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Walk to Lake
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Fireplace · Lake · Waterfront ·
From
$143/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Fireplace
Lake
Waterfront
Mountains
Fitness Center
Dishwasher
Oven
In Unit Laundry
Other spaces
Kitchen
Cozy 2 bedroom apartment 2 miles from historic Winchester.
9.2

Excellent

·
Winchester
·
2 br
·
Sleeps 4
·
Oven · Assigned Parking · Kitchen ·
From
$121/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Oven
Assigned Parking
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace
The George Washington - A Wyndham Grand Hotel
8.8

Very good

·
Winchester
·
1 br
·
Sleeps 5
·
Hot Tub · Assigned Parking · Outdoor Space ·
From
$89/night
Check availability
Property
Hotel · 1 Bed
Amenities
Hot Tub
Assigned Parking
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace
APM Inn and Suites
6.6

Good

·
Winchester
·
1 br
·
Sleeps 2
·
Hardwood Floor · Assigned Parking · Smoking Allowed ·
From
$34/night
Check availability
Property
Hotel · 1 Bed
Amenities
Hardwood Floor
Assigned Parking
Smoking Allowed
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Comfort Inn & Suites
8.9

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Carpet · Smoking Allowed · Free Parking ·
From
$76/night
Check availability
Property
Hotel · 1 Bed
Amenities
Carpet
Smoking Allowed
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Business Center
Other spaces
Workspace
La Quinta by Wyndham Winchester
8.4

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Carpet · In Unit Laundry · Smoking Allowed ·
From
$84/night
Check availability
Property
Hotel · 1 Bed
Amenities
Carpet
In Unit Laundry
Smoking Allowed
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Other spaces
Workspace
Travelodge by Wyndham Winchester
6.9

Good

·
Winchester
·
1 br
·
Sleeps 4
·
Pool · Free Parking · On Site Laundry ·
From
$51/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Business Center
Other spaces
Workspace
Holiday Inn Winchester Southeast-Historic Gateway, an IHG Hotel
8.5

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Carpet · Smoking Allowed · Pool ·
From
$73/night
Check availability
Property
Hotel · 1 Bed
Amenities
Carpet
Smoking Allowed
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace

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Wingate by Wyndham Winchester
8.2

Very good

·
Winchester
·
1 br
·
Sleeps 10
·
Pool · Free Parking · On Site Laundry ·
From
$76/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Fitness Center
Dry Cleaning Service
Other spaces
Workspace
Candlewood Suites Winchester, an IHG Hotel
8.3

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Dishwasher · Oven · Carpet ·
From
$77/night
Check availability
Property
Hotel · 1 Bed · 1 bath
Amenities
Dishwasher
Oven
Carpet
Smoking Allowed
Free Parking
On Site Laundry
Wifi
Air Conditioning
Other spaces
Kitchen, Workspace
Super 8 by Wyndham Winchester VA
6.1

Good

·
Winchester
·
1 br
·
Sleeps 4
·
Free Parking · On Site Laundry · Workspace ·
From
$53/night
Check availability
Property
Hotel · 1 Bed
Amenities
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Storage
Other spaces
Workspace
Sleep Inn & Suites
7.7

Very good

·
Winchester
·
1 br
·
Sleeps 10
·
Assigned Parking · Carpet · Pool ·
From
$68/night
Check availability
Property
Hotel · 1 Bed · 1 bath
Amenities
Assigned Parking
Carpet
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace
Country Inn & Suites by Radisson, Winchester, VA
8.3

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Hardwood Floor · Assigned Parking · Outdoor Space ·
From
$80/night
Check availability
Property
Hotel · 1 Bed
Amenities
Hardwood Floor
Assigned Parking
Smoking Allowed
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Other spaces
Workspace
Motel 6-Winchester, VA
7.4

Very good

·
Winchester
·
2 br
·
Sleeps 4
·
Workspace · Wifi · Air Conditioning ·
From
$53/night
Check availability
Property
Hotel · 2 Beds
Amenities
Wifi
Air Conditioning
Furnished
Wheelchair Accessible
Other spaces
Workspace
Hilton Garden Inn Winchester
9

Excellent

·
Winchester
·
1 br
·
Sleeps 4
·
Outdoor Space · Smoking Allowed · Pool ·
From
$109/night
Check availability
Property
Hotel · 1 Bed
Amenities
Smoking Allowed
Pool
Free Parking
On Site Laundry
Air Conditioning
Furnished
Fitness Center
Residents Lounge
Other spaces
Workspace
Hampton Inn Winchester
8.8

Very good

·
Winchester
·
1 br
·
Sleeps 5
·
Ski In Ski Out · Assigned Parking · Smoking Allowed ·
From
$104/night
Check availability
Property
Hotel · 1 Bed
Amenities
Ski In Ski Out
Assigned Parking
Smoking Allowed
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Other spaces
Workspace
Hampton Inn Winchester-University/ Mall
8.7

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Carpet · Smoking Allowed · Pool ·
From
$104/night
Check availability
Property
Hotel · 1 Bed
Amenities
Carpet
Smoking Allowed
Pool
Free Parking
On Site Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace
Fairfield Inn and Suites by Marriott Winchester
8.3

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Carpet · Pool · Free Parking ·
From
$67/night
Check availability
Property
Hotel · 1 Bed
Amenities
Carpet
Pool
Free Parking
On Site Laundry
Air Conditioning
Furnished
Fitness Center
Dry Cleaning Service
Other spaces
Workspace
Courtyard by Marriott Winchester Medical Center
8.4

Very good

·
Winchester
·
1 br
·
Sleeps 5
·
Hot Tub · Pool · Free Parking ·
From
$76/night
Check availability
Property
Hotel · 1 Bed
Amenities
Hot Tub
Pool
Free Parking
On Site Laundry
Air Conditioning
Furnished
Fitness Center
Residents Lounge
Other spaces
Workspace
TownePlace Suites Winchester
8.8

Very good

·
Winchester
·
1 br
·
Sleeps 5
·
Dishwasher · Kitchen · Free Parking ·
From
$83/night
Check availability
Property
Hotel · 1 Bed
Amenities
Dishwasher
Free Parking
On Site Laundry
Air Conditioning
Furnished
Business Center
Fitness Center
Dry Cleaning Service
Other spaces
Kitchen, Workspace
Clean, neat, peace and quiet
2

Poor

·
Winchester
·
1 br
·
Sleeps 2
·
Fitness Center · In Unit Laundry · On Site Laundry ·
From
$43/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Fitness Center
In Unit Laundry
On Site Laundry
Wifi
Air Conditioning
Furnished
Wheelchair Accessible
Other spaces
Workspace
Modern Upscale Home, Historic Downtown Winchester
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · Assigned Parking ·
From
$200/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
Assigned Parking
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
NEW! The Overlook

No reviews

·
Winchester
·
4 br
·
Sleeps 11
·
Dishwasher · In Unit Laundry · Outdoor Space ·
From
$304/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Residents Lounge
Other spaces
Kitchen
Lofts for weekly rentals! 2 miles from historic downtown.

No reviews

·
Winchester
·
2 br
·
Sleeps 2
·
In Unit Laundry · Outdoor Space · Kitchen ·
From
$60/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
In Unit Laundry
Wifi
Furnished
Other spaces
Kitchen
Colonial Getaway Near Old Town Historic Winchester
9.9

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · Carpet ·
From
$148/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Dishwasher
Oven
Carpet
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
City Charmer near Historic OldTown Winchester.
10

Excellent

·
Winchester
·
2 br
·
Sleeps 4
·
Hardwood Floor · Oven · In Unit Laundry ·
From
$111/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Hardwood Floor
Oven
In Unit Laundry
On Site Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Showing 1 - 26 of 26 results
Home > Virginia Vacation Rentals > Winchester Vacation Rentals
Updated: March 21, 2023

Learn about vacation rentals in

Winchester

Explore 27 vacation rentals near Winchester, Virginia. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winchester, you can see photos of Winchester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winchester vacation rentals in specific areas. Whether you’re looking for a Winchester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winchester is $34 per night and the highest price is $304 per night.
2 of the vacation rentals near Winchester are apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation units is $90 per night. There are currently 1 vacation units under this price. 6 of the vacation rentals near Winchester are houses. The average bathroom count for a vacation house near Winchester is 2. The average price for vacation houses near Winchester is $129 per night. There are 3 vacation homes under this price. The most common amenities for vacation rentals near Winchester are: furnished, air conditioning, and wifi. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

18 available

2 bed rentals

4 available

3 bed rentals

4 available

4+ bed rentals

1 available

Vacation Rentals in Winchester, VA FAQ

How many vacation rentals in Winchester are available?

There are currently 27 vacation rentals in Winchester available. Our vacation rentals in Winchester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Winchester?

Yes, right now there are 12 pet friendly vacation rentals in Winchester. A pet friendly vacation rental in Winchester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Winchester with a pool?

Yes there are vacation rentals with a pool available in Winchester, VA. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Winchester with internet access?

As of March 21, 2023, there are vacation rentals with internet access available in Winchester, Virginia. Check out more enjoyable destinations on Vacations by Zumper.

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