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Vacations by Zumper

Vacation Rentals in Winchester, VA

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Winchester, VA

Book a vacation rental in Winchester that has the highest visitor rating. Here are 6 of the best vacation rentals in Winchester.
Private and Spacious Vacation House on a 5acre lot 12 mins from Wichester city!!
10

Excellent

·
Winchester
·
4 br
·
Sleeps 12
·
Air Conditioning · Hardwood Floor · Wifi ·
From
$171/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Hardwood Floor
Wifi
Assigned Parking
Mountains
On Site Laundry
Oven
Fitness Center
Other spaces
Workspace, Kitchen
City Charmer near Historic OldTown Winchester.
10

Excellent

·
Winchester
·
2 br
·
Sleeps 4
·
Furnished · Kitchen · On Site Laundry ·
From
$109/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Furnished
On Site Laundry
Hardwood Floor
Wifi
Air Conditioning
Oven
Other spaces
Kitchen
Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Walk to Lake
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Fitness Center · On Site Laundry · Air Conditioning ·
From
$178/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Fitness Center
On Site Laundry
Air Conditioning
Oven
Mountains
Fireplace
Furnished
Lake
Other spaces
Kitchen
Colonial Getaway near Old Town Historic Winchester
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Outdoor Space · Air Conditioning · Furnished ·
From
$154/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Air Conditioning
Furnished
Oven
Carpet
Wifi
In Unit Laundry
Dishwasher
Other spaces
Kitchen
Affordable Winchester Get Away! Sleeps 6
10

Excellent

·
Winchester
·
1 br
·
Sleeps 6
·
In Unit Laundry · Furnished · Dishwasher ·
From
$125/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
In Unit Laundry
Furnished
Dishwasher
Air Conditioning
Mountains
Wifi
Fitness Center
Oven
Other spaces
Kitchen
Price drop
NEW! The Overlook
10

Excellent

·
Winchester
·
4 br
·
Sleeps 11
·
Kitchen · Dishwasher · Mountains ·
From
$175/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Dishwasher
Mountains
Air Conditioning
Furnished
Wifi
Residents Lounge
In Unit Laundry
Other spaces
Kitchen

Our Recommended Vacation Rentals in Winchester, VA

We analyzed vacation rentals in Winchester from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Winchester to help you find a deal for your next trip.
Historic District Downtown Winchester

No rating

·
Winchester
·
1 br
·
Sleeps 2
·
Business Center · Furnished · Kitchen ·
From
$169/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Business Center
Furnished
Other spaces
Kitchen
Price drop
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.

No rating

·
Winchester
·
2 br
·
Sleeps 6
·
Air Conditioning · Dishwasher · Fireplace ·
From
$137/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Fireplace
Furnished
Wifi
On Site Laundry
Oven
Other spaces
Kitchen
Escape to The Bird's Nest, a charming tiny home nestled on a sprawling 62-acre farm

No rating

·
Winchester
·
Studio
·
Sleeps 2
·
Kitchen · Air Conditioning · Furnished ·
From
$81/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Air Conditioning
Furnished
On Site Laundry
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Winchester, VA

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Winchester starting at $34. Use the price filter at the top of the page to search for more specific prices.
APM Inn and Suites
6.6

Good

·
Winchester
·
1 br
·
Sleeps 2
·
Kitchen · Smoking Allowed · Furnished ·
From
$34/night
Check availability
Property
Hotel · 1 Bed
Amenities
Smoking Allowed
Furnished
Hardwood Floor
On Site Laundry
Wheelchair Accessible
Elevator
Air Conditioning
Swimming Pool
Other spaces
Kitchen
44 S Loudoun St ##5

No rating

·
Winchester
·
1 br
·
Air Conditioning · Brick · Ceiling Fan ·
From
$40/night
Min stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Brick
Ceiling Fan
131 S Purcell Ave

No rating

·
Winchester
·
2 br
·
Air Conditioning ·
From
$45/night
Min stay: 30 nights
Property
Apartment · 2 Beds · 1 bath
Amenities
Air Conditioning
Price drop
Clean, neat, peace and quiet
4

Good

·
Winchester
·
1 br
·
Sleeps 2
·
Furnished · Wheelchair Accessible · Air Conditioning ·
From
$46/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Furnished
Wheelchair Accessible
Air Conditioning
On Site Laundry
Wifi
Fitness Center
In Unit Laundry
Other spaces
Workspace
Travelodge by Wyndham Winchester
7

Very good

·
Winchester
·
1 br
·
Sleeps 4
·
Free Parking · Business Center · Workspace ·
From
$51/night
Check availability
Property
Hotel · 1 Bed
Amenities
Free Parking
Business Center
Furnished
On Site Laundry
Pool
Swimming Pool
Air Conditioning
Wifi
Other spaces
Workspace
Motel 6-Winchester, VA
7.4

Very good

·
Winchester
·
2 br
·
Sleeps 4
·
Workspace · Furnished · Wheelchair Accessible ·
From
$53/night
Check availability
Property
Hotel · 2 Beds
Amenities
Furnished
Wheelchair Accessible
Wifi
Air Conditioning
Other spaces
Workspace
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Updated: September 25, 2023