Chester Gap Vacations

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Photo by Brian V. Rowe

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Your Chester Gap Vacation

Our vacation packages to Chester Gap let you customize your own adventure. Tailor your getaway to suit your interests and needs and make every moment count in this interesting city. Hoping to sightsee? Spend your days enjoying major attractions like Rappahannock Cellars during your trip to Chester Gap. A couple of quick clicks is all it takes to create a customized Chester Gap vacation on Expedia.

Chester Gap Hotel Deals

Modern Mountain Retreat w/ Deck + Hot Tub!

Modern Mountain Retreat w/ Deck + Hot Tub!

Chester Gap
9.8/10 Exceptional! (60 reviews)
Overall great
"We had a wonderful long weekend at this rental with two families (4 adults, 2 toddlers, and 1 dog). The house was as described—clean, comfortable, and very well-equipped. The kitchen was impressively stocked with everything we needed to cook meals, and we especially appreciated the thoughtful extras ..."

Reviewed on Jun 26, 2025

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Modern Mountain Retreat w/ Deck + Hot Tub!
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
$97 nightly
The price is $105 total per night from Sep 7 to Sep 8
$105 total
Sep 7 - Sep 8
Total with taxes and 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
$114 nightly
The price is $127 total per night from Sep 7 to Sep 8
$127 total
Sep 7 - Sep 8
Total with taxes and 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
See all 493 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.

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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?
You can usually find lower prices and greater availability in September, October and December. Browse our cheap Chester Gap vacation packages and you could get some excellent off-season deals.
How many days is enough for Chester Gap?
The ideal duration for your Chester Gap vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to go to all the top attractions and explore 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.
Does Expedia offer Book Now, Pay Later Chester Gap vacation packages?
If you're like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Chester Gap vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.