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

Top hotels in Gerrardstown

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$145 per night from 6 Jul to 7 Jul
S$145
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (2,058 reviews)
"Very good!"

Reviewed on 21 Jun, 2025

La Quinta 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 S$97 per night from 3 Jul to 4 Jul
S$97
3 Jul - 4 Jul
includes taxes & fees
8.2/10 Very Good! (1,102 reviews)
"This is a great place to stop if you are going north or south on 81. Easy off and easy on. Good renovations and lots of places to eat and shop. We will definitely consider staying again here!"

Reviewed on 19 Jun, 2025

Travelodge 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$134 per night from 29 Jun to 30 Jun
S$134
29 Jun - 30 Jun
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Great location,the hotel was very nice and the breakfast was great."

Reviewed on 20 Jun, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 905 properties in Gerrardstown
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.

Frequently asked questions

How much does a Gerrardstown holiday package cost?
You'll find cheap prices on Expedia for your Gerrardstown break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Gerrardstown costs.
What are the cheapest months to go to Gerrardstown?
To score cheap Gerrardstown holiday packages, plan your trip outside of peak times such as school holidays. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Gerrardstown?
Generally, a handful of days is enough to explore the major sights during your Gerrardstown holiday. But if you'd like to have some time to unwind or take day tours, think about extending your itinerary.
How to find the best Gerrardstown package deals?
Start your search for a Gerrardstown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Gerrardstown package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gerrardstown escape underway.
Is it cheaper to book a Gerrardstown holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a customised Gerrardstown holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Gerrardstown?
Secure amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Gerrardstown trip.
How to plan a trip to Gerrardstown?

  1. Choose when to get away: Check your schedule and pack your bags. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Gerrardstown.
  2. Plan your budget wisely: On top of the cost of your accommodation, you should consider other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Gerrardstown.
  3. Work out your trip length: Think about how much time you want to spend discovering Gerrardstown. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Gerrardstown holiday package.

* 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.