Chester Gap Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

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    Save up to ₩234,741 when you book a flight and hotel together*
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Find the Best Chester Gap Vacation Packages

Chester Gap Hotel Deals

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is ₩134,644 per night from Sep 14 to Sep 15
₩134,644
₩146,492 total
Sep 14 - Sep 15
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"This location is always my overnight stop when traveling . Highly recommend."

Reviewed on Aug 20, 2025

Comfort Inn & Suites Winchester
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd, Front Royal, VA
Fully refundableReserve now, pay when you stay
The price is ₩164,171 per night from Sep 7 to Sep 8
₩164,171
₩182,722 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Excellent hotel, spotty wifi
"The employee at check-in was welcoming, friendly, and helpful; the room was clean and quiet. This was an excellent Hampton experience. The wifi with the free Hilton Honors login was sub-par, which put a damper on my ability to work during my stay."

Reviewed on Aug 24, 2025

Hampton Inn Front Royal
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
The price is ₩99,211 per night from Sep 2 to Sep 3
₩99,211
₩110,422 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"The hotel was very clean. The coffee and complimentary breakfast-very disappointing compared to what we get at the Hampton Inn. I tried to check in early (1pm) and was told I would have to pay $20… no other place we stayed has ever required an early check in fee. The place was empty."

Reviewed on Aug 25, 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
See all 497 properties in Chester Gap
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 Chester Gap vacation package cost?
You'll find cheap prices on Expedia for your Chester Gap getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Chester Gap costs.
What are the cheapest months to go to Chester Gap?
To pick up cheap Chester Gap vacation packages, plan your trip outside of peak periods such as public holidays. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Chester Gap?
The ideal length of your Chester Gap vacation depends on what you'd like to do and see. Generally, a few days to a week will give you plenty of time to check out all the major sights and discover some hidden treasures along the way.
How to find the best Chester Gap package deals?
Use Expedia's filters to help you find some terrific Chester Gap package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Chester Gap package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Chester Gap vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can customize your Chester Gap getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chester Gap?
Score incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Chester Gap escape.
How to plan a trip to Chester Gap?

  1. Choose your travel dates: What you'd like to do in Chester Gap and your favorite season will help you decide when to get away.
  2. Set a budget: Factor in costs such as flights, meals and transportation when working out how much to set aside for your trip to Chester Gap. Then, choose a property that matches your budget, whether that's a low-cost option or a more luxurious retreat.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you'd like to get to in Chester Gap. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Chester Gap vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.