Chester Gap Vacations

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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

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 Feb 8 to Feb 9
$105 total
Feb 8 - Feb 9
Total with taxes and fees
9.4/10 Exceptional! (1,092 reviews)
Clean room

Reviewed on Jan 9, 2026

Comfort Inn & Suites Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $81 total per night from Jan 19 to Jan 20
$81 total
Jan 19 - Jan 20
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Breakfast fresh, good coffee, enough healthy variety

Reviewed on Jan 6, 2026

Ramada by Wyndham Strasburg/Shenandoah Valley
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
Fully refundable
$83 nightly
The price is $90 total per night from Jan 25 to Jan 26
$90 total
Jan 25 - Jan 26
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
It was all totally smooth

Reviewed on Jan 7, 2026

Country Inn & Suites by Radisson, Winchester, VA
See all 514 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.

Find the Best Chester Gap Vacation Packages

Chester Gap Essential Information

Language
English
Currency
U.S dollars
Population
840

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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.