Glengary Holidays

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Top hotels in Glengary

Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is S$127 per night from 26 Jul to 27 Jul
S$127
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on 28 Jun, 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is S$131 per night from 19 Jul to 20 Jul
S$131
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Staff was really great!!"

Reviewed on 3 Jul, 2026

TRU By Hilton 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$130 per night from 26 Jul to 27 Jul
S$130
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Comfortable clean room. Bathroom could use an upgrade. Shower head flow could not be changed to a softer setting. Also one of the few hotel chains that doesn’t offer a free breakfast. At $10 pp, Wawa is not far and has good food and coffee."

Reviewed on 3 Jul, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 676 properties in Glengary
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 Glengary holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Glengary costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Glengary?
You can generally find lower rates and greater availability in January, February and April. Check out our cheap Glengary holiday packages and you could score some great off-season discounts.
How many days is enough for Glengary?
Usually, a handful of days is enough to explore the main sights during your Glengary holiday. But if you prefer to have some time to unwind or take day trips, consider extending your itinerary.
How to find the best Glengary package deals?
Use Expedia's filters to find some tempting Glengary package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Glengary package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Glengary holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging accommodation and flights separately. Better still, you can tailor your Glengary trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Glengary?
If you're considering a spontaneous Glengary holiday, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Glengary?

  1. Pick your dates: The things you want to do in Glengary and your preferred season will help you decide when to travel.
  2. Plan your budget wisely: In addition to the price of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that may crop up during your trip to Glengary.
  3. Decide how long to go for: Now that you know more about Glengary, you can work out the ideal length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Glengary holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* 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.