The average price of a 7-day trip to Winchester is $1,607 for a solo traveler, $2,886 for a couple, and $5,411 for a family of 4. Winchester hotels range from $58 to $264 per night with an average of $82, while most vacation rentals will cost $180 to $1000 per night for the entire home. Average worldwide flight costs to Blue Grass Airport (LEX) are between $671 and $947 per person for economy flights and $2,106 to $2,972 for first class. Depending on activities, we recommend budgeting $39 to $86 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, KY, US
On average, these will be the cheapest dates to fly to LEX and stay in a Winchester hotel:
- January 8th to March 11th
- May 28th to June 10th
- August 13th to December 9th (except the weeks of October 15th, October 22nd and November 26th)
The absolute cheapest time to take a vacation in Winchester is usually early September.
Average Winchester Trip Costs
Average Solo Traveler
The average cost for one person to visit Winchester for a week is $1,199-$2,331($171-$333 per day)
Food, Travel, and Sightseeing: $39 to $86 per day for one person’s daily expenses
Flights: $434 to $805 for economy
Lodging: $82 to $97 per night for one 2 or 3-star hotel room
or $126 to $154 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 $2,380-$4,022($340-$575 per day)
Food, Travel, and Sightseeing: $78 to $172 per day for two people’s daily expenses
Flights: $868 to $1,610 for economy
Lodging: $82 to $97 per night for one 2 or 3-star hotel room
or $126 to $154 per night for a 1-bed vacation rental
Average Family Vacation
The average cost for 4 people to visit Winchester for a week is $3,812-$7,014($545-$1,002 per day)
Food, Travel, and Sightseeing: $156 to $344 per day for four people’s daily expenses
Flights: $1,736 to $3,220 for economy
Lodging: $164 to $194 per night for two 2 or 3-star hotel rooms
or $189 to $231 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 $126 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 $160 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 $49.
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 $882-$2,193($126-$313 per day)
Food, Travel, and Sightseeing: $22 to $44 per day for one person’s daily expenses
Flights: $434 to $805 for economy
Lodging: $49 to $58 per night for one 1-star hotel room
or $160 to $180 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 $1,470-$3,306($210-$472 per day)
Food, Travel, and Sightseeing: $44 to $88 per day for two people’s daily expenses
Flights: $868 to $1,610 for economy
Lodging: $49 to $58 per night for one 1-star hotel room
or $160 to $180 per night for a 1-bed vacation rental
Budget Family Vacation
The lowest cost for 4 people to visit Winchester for a week is $2,940-$6,180($420-$883 per day)
Food, Travel, and Sightseeing: $88 to $176 per day for four people’s daily expenses
Flights: $1,736 to $3,220 for economy
Lodging: $98 to $116 per night for two 1-star hotel rooms
or $224 to $288 per night for a 2-bed vacation rental
Overall it is harder 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 $2,274-$16,230($325-$2,319 per day)
Food, Travel, and Sightseeing: $70 to $181 per day for one person’s daily expenses
Flights: $998 to $1,763 for first class
Lodging: $131 to $264 per night for one 4 or 5-star hotel room
or $1,000 to $2,200 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 $3,762-$19,260($537-$2,751 per day)
Food, Travel, and Sightseeing: $140 to $362 per day for two people’s daily expenses
Flights: $1,996 to $3,526 for first class
Lodging: $131 to $264 per night for one 4 or 5-star hotel room
or $1,000 to $2,200 per night for a preferred vacation rental
Luxury Family Vacation
The high-end price for 4 people to visit Winchester for a week is $7,524-$33,240($1,075-$4,749 per day)
Food, Travel, and Sightseeing: $280 to $724 per day for four people’s daily expenses
Flights: $3,992 to $7,052 for first class
Lodging: $262 to $528 per night for two 4 or 5-star hotel rooms
or $1,600 to $3,520 per night for a preferred vacation rental
Winchester Hotel Prices
The cost of staying in Winchester is higher 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 a healthy amount of vacation rentals serving all budgets in Winchester.
Flight Costs to Winchester
Averaging flights around the world, prices go from a high of $947 average in late July to a low of $671 in early September. Median flight price is $654. These prices are based on millions of flights. For Winchester our data includes 514 originating airports, and 108 airlines. The area has average variance in price compared with other locations. Flying to Winchester from an airport like Shevchenko (SCO) in Aktau (Kazakhstan) for an average $6,106 trip fare will obviously cost a lot more than from an airport like St Pete Clearwater International (PIE) in St. Petersburg, FL (the United States) at an average of just $196.
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 $276, so you can easily save about 41% 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 $330 per person or more, while a standard nice meal might be about $22 per person. Private tours can cost $659 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.