The average price of a 7-day trip to Winchester is $1,675 for a solo traveler, $3,008 for a couple, and $5,640 for a family of 4. Winchester hotels range from $53 to $240 per night with an average of $83, while most vacation rentals will cost $160 to $520 per night for the entire home. Average worldwide flight costs to Washington Dulles International Airport (IAD) are between $774 and $1,296 per person for economy flights and $2,429 to $4,067 for first class. Depending on activities, we recommend budgeting $42 to $85 per person per day for transportation and enjoying local restaurants.
See below for average, budget, and luxury trip costs. You can also look up flight costs from your airport for more tailored flight pricing.
The Cheapest Times to Visit Winchester, VA, US
On average, these will be the cheapest dates to fly to IAD and stay in a Winchester hotel:
- January 15th to March 11th (except the week of February 26th)
- April 23rd to June 3rd (except the week of May 7th)
- August 6th to November 18th (except the week of October 15th)
The absolute cheapest time to take a vacation in Winchester is usually mid to late September.
Average Winchester Trip Costs
Average Solo Traveler
The average cost for one person to visit Winchester for a week is $1,243-$2,489($178-$356 per day)
Food, Travel, and Sightseeing: $42 to $85 per day for one person’s daily expenses
Flights: $463 to $1,102 for economy
Lodging: $81 to $94 per night for one 2 or 3-star hotel room
or $108 to $132 per night for a 1-bed vacation rental
Average Couple’s Trip
The average cost for a couple to visit Winchester for a week is $2,622-$4,574($375-$653 per day)
Food, Travel, and Sightseeing: $84 to $170 per day for two people’s daily expenses
Flights: $926 to $2,204 for economy
Lodging: $81 to $94 per night for one 2 or 3-star hotel room
or $108 to $132 per night for a 1-bed vacation rental
Average Family Vacation
The average cost for 4 people to visit Winchester for a week is $4,000-$8,054($571-$1,151 per day)
Food, Travel, and Sightseeing: $168 to $340 per day for four people’s daily expenses
Flights: $1,852 to $4,408 for economy
Lodging: $162 to $188 per night for two 2 or 3-star hotel rooms
or $162 to $211 per night for a 2-bed vacation rental
Traveling Cheap to Winchester
How cheap can you make a vacation to Winchester? The cheapest trip to Winchester is about $123 per person per day for travelers willing to take standby flights, deal with inconvenience, and otherwise limit travel expenses. About 0% of rentals are available in the $0 to $100 range for an entire place, and vacation rentals can be booked for as low as $140 per night. These inexpensive rentals must be booked as early as possible and may not be in the most desirable areas. 1-star hotels are more likely to be available, with rooms starting at around $43.
Even cheaper trips are possible depending on where you live and whether you can drive. Check the cheapest times to fly for more saving ideas.
Budget Solo Traveler
The lowest cost for one person to visit Winchester for a week is $861-$2,402($123-$343 per day)
Food, Travel, and Sightseeing: $20 to $40 per day for one person’s daily expenses
Flights: $463 to $1,102 for economy
Lodging: $43 to $53 per night for one 1-star hotel room
or $140 to $170 per night for a 1-bed vacation rental
Budget Couple’s Trip
The lowest cost for a couple to visit Winchester for a week is $1,464-$3,784($209-$541 per day)
Food, Travel, and Sightseeing: $40 to $80 per day for two people’s daily expenses
Flights: $926 to $2,204 for economy
Lodging: $43 to $53 per night for one 1-star hotel room
or $140 to $170 per night for a 1-bed vacation rental
Budget Family Vacation
The lowest cost for 4 people to visit Winchester for a week is $2,928-$6,956($418-$994 per day)
Food, Travel, and Sightseeing: $80 to $160 per day for four people’s daily expenses
Flights: $1,852 to $4,408 for economy
Lodging: $86 to $106 per night for two 1-star hotel rooms
or $224 to $238 per night for a 2-bed vacation rental
Overall it is possible but not easy to travel to Winchester cheaply.
The Cost of a Luxury Winchester Trip
There is no true ceiling on the cost of a luxury trip, so our estimates are based on what most people do in Winchester.
Luxury Solo Traveler
The high-end price for one person to visit Winchester for a week is $2,191-$10,022($313-$1,432 per day)
Food, Travel, and Sightseeing: $76 to $153 per day for one person’s daily expenses
Flights: $945 to $2,711 for first class
Lodging: $119 to $240 per night for one 4 or 5-star hotel room
or $520 to $1,040 per night for a preferred vacation rental
Luxury Couple’s Trip
The high-end price for a couple to visit Winchester for a week is $3,668-$13,804($524-$1,972 per day)
Food, Travel, and Sightseeing: $152 to $306 per day for two people’s daily expenses
Flights: $1,890 to $5,422 for first class
Lodging: $119 to $240 per night for one 4 or 5-star hotel room
or $520 to $1,040 per night for a preferred vacation rental
Luxury Family Vacation
The high-end price for 4 people to visit Winchester for a week is $7,336-$23,864($1,048-$3,409 per day)
Food, Travel, and Sightseeing: $304 to $612 per day for four people’s daily expenses
Flights: $3,780 to $10,844 for first class
Lodging: $238 to $480 per night for two 4 or 5-star hotel rooms
or $728 to $1,456 per night for a preferred vacation rental
Winchester Hotel Prices
The cost of staying in Winchester is about average than the average city. On average hotels are less expensive than vacation rentals. Luxury vacation rentals are more expensive in Winchester due to very high property costs. The graphs below show how much cost can vary depending on the type of experience you’re looking for.
Winchester Lodging Cost by Star Status
The average price for the class of hotel is on the (y) axis. The hotel class (out of 5 stars) is on the (x) axis.
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Prices are based on Winchester hotel averages and may not reflect current prices. In some cases, we extrapolate prices to estimate costs, and hotels with your desired star rating may not be available.
Vacation Rental Prices
The percent of vacation rentals in the price range is on the left (y) axis. Price range is on the bottom (x) axis.
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There are many options for vacation rentals across many price ranges in Winchester.
Flight Costs to Winchester
Averaging flights around the world, prices go from a high of $1,296 average in early January to a low of $774 in mid to late September. Median flight price is $819. These prices are based on millions of flights. For Winchester our data includes 1,471 originating airports, and 190 airlines. The area has more variance in price compared with other locations. Flying to Winchester from an airport like Savannakhet (ZYL) in Sylhet (Bangladesh) for an average $9,851 trip fare will obviously cost a lot more than from an airport like Shenandoah Valley Regional (SHD) in Staunton, VA (the United States) at an average of just $151.
Average Flight Cost by Season
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Average Flight Cost by Day of Week
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The cheapest day to fly in is typically Tuesday, and the cheapest day to fly back is usually Tuesday. Click here to see data for the cost of flights from your airport. In Winchester, the difference between the cheapest and the most expensive week is about $522, so you can easily save about 67% simply by using our free flight guides and booking in advance.
Daily Expenses Budget
Daily vacation expenses vary more based on what you’re interested in doing. A fine dining restaurant with drinks around Winchester can easily cost $300 per person or more, while a standard nice meal might be about $20 per person. Private tours can cost $597 per day, but self-guided tours to see the outdoor sights can be free. Costs vary wildly, so recommendations are made based on the cost of living and averages we see for this type of vacation.