Glengary Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Ready to book your vacation to Glengary?

 

Choose your dates

Glengary Hotel Deals

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 CA $141 per night from Sep 1 to Sep 2
CA $141
CA $154 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,137 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."

Reviewed on Aug. 25, 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 CA $109 per night from Sep 15 to Sep 16
CA $109
CA $119 total
Sep 15 - Sep 16
includes taxes & fees
9/10 Wonderful! (1,326 reviews)
"It was a great experiencia. It was really clean and the staff was exactly friendly and accommodated"

Reviewed on Aug. 24, 2025

Microtel 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 CA $113 per night from Sep 1 to Sep 2
CA $113
CA $127 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Clean and staff was great."

Reviewed on Aug. 23, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 627 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Glengary vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation to Glengary costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Glengary?
January, February and April are the best times to search for cheap Glengary vacation packages. Opting to travel in quieter periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Glengary?
With a well-planned itinerary, you can easily tick off the most popular Glengary attractions in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Glengary vacation for longer.
How to find the best Glengary package deals?
Use Expedia's filter tool to find some fabulous Glengary package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Glengary package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Glengary vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Glengary vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Glengary?
If you're planning an impromptu Glengary adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Glengary?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Glengary.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Glengary.
  3. Work out your trip length: Consider how long you want to spend exploring Glengary. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Glengary vacation 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.