Winchester Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Winchester

Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is S$96 per night from 20 Jul to 21 Jul
S$96
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (1,099 reviews)
"Staff friendly and helpful.. room was clean and bed very comfortable."

Reviewed on 9 Jul, 2025

Travelodge by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is S$161 per night from 22 Jul to 23 Jul
S$161
22 Jul - 23 Jul
includes taxes & fees
9/10 Wonderful! (2,078 reviews)
"Walk in shower convenient. The pillows are uncomfortable, lumpy."

Reviewed on 10 Jul, 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is S$128 per night from 27 Jul to 28 Jul
S$128
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Staff was courteous and helpful."

Reviewed on 9 Jul, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 1,996 properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What to do in Winchester

Shenandoah National Park Self-Driving Audio Tour

Shenandoah Tour: Self-Guided Drive

S$22
per traveller
96% of travellers recommend
Shenandoah Tour: Self-Guided Drive
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchester?
If you'd like to score a cheap Winchester holiday package, consider travelling in December, January and February. You're likely to find better prices on flights and accommodation during these months --- perfect for travellers wishing to save money.
How many days is enough for Winchester?
Allow around 2 days for your Winchester holiday in order to enjoy everything that makes this place unique. Wander around key areas, including Old Town Winchester and College Park. Then check out major sights like Abram's Delight and Museum of the Shenandoah Valley. With a clever itinerary, you can keep busy with room for some rest time too. Want to go beyond Winchester? Consider fitting in an excursion or two.
Is it worth booking a holiday package to Winchester?
It's easy to see why a Winchester holiday is on the to-do list of many travellers. Top attractions like Shenandoah Valley Discovery Museum are just the start of what you can explore here.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester escape underway.
Is it cheaper to book a Winchester holiday as a package?
You can enjoy significant savings on your next Winchester retreat by booking a tailored holiday package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Winchester?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winchester trip.
How to plan a trip to Winchester?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the activities available will also help you decide when to holiday in Winchester.
  2. Set a budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Winchester. Then, pick a property that fits your budget, whether that's a wallet-friendly option or a more luxurious retreat.
  3. Decide how long to go for: Now that you know more about Winchester, you can figure out the perfect length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Winchester holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.