Winchester Holidays

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Top hotels in 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 Rp1.692.384 per night from 30 Jul to 31 Jul
Rp1.692.384
Rp1.841.386 total
30 Jul - 31 Jul
includes taxes & fees
9.2/10 Wonderful! (2,091 reviews)
"Good overnight stop. Clean"

Reviewed on 25 Jul 2025

La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is Rp1.335.302 per night from 17 Aug to 18 Aug
Rp1.335.302
Rp1.452.809 total
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,321 reviews)
"Nice hotel. The dog fee is a bit high."

Reviewed on 27 Jul 2025

Microtel Inn & Suites by Wyndham 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 Rp1.142.400 per night from 30 Jul to 31 Jul
Rp1.142.400
Rp1.242.931 total
30 Jul - 31 Jul
includes taxes & fees
8.4/10 Very Good! (1,096 reviews)
"Hotel was right off highway, very inexpensive, unexpectedly provided light breakfast (waffles, cereal, toast, coffee, juice). Would stay there again."

Reviewed on 23 Jul 2025

Travelodge by Wyndham Winchester
See all 2,001 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.

Popular places to visit

Old Court House Civil War Museum

You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Old Court House Civil War Museum

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.