Chester Gap Holidays

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Photo by Brian V. Rowe

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Your Chester Gap Holiday

When a city adventure is calling your name, answer it with a Chester Gap holiday package. With all your travel needs taken care of before you leave, all you have to do here is focus on having fun. Want to see the sights but don't know where to begin? Every trip to Chester Gap should include Rappahannock Cellars. Browse Expedia's extensive range of travel options and start organising your perfect holiday to Chester Gap now.

Chester Gap Holiday

Chester Gap Essential Information

Language
English
Currency
U.S dollars
Population
840
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Skyline Caverns, Shenandoah River State Park and Linden Vineyards

Our pick of the best Chester Gap Hotel Deals

Modern Mountain Retreat w/ Deck + Hot Tub!

Modern Mountain Retreat w/ Deck + Hot Tub!

Chester Gap
Get rates
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
The price is AU$162 per night from 7 Sept to 8 Sept
AU$162
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"This location is always my overnight stop when traveling . Highly recommend."

Reviewed on 20 Aug. 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 AU$195 per night from 21 Sept to 22 Sept
AU$195
21 Sept - 22 Sept
includes taxes & fees
Hampton Inn Front Royal
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chester Gap holiday 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 holiday to Chester Gap costs.
What are the cheapest months to go to Chester Gap?
To pick up cheap Chester Gap holiday 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Chester Gap holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and accommodation separately. Better still, you can customise 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 holiday 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 favourite 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 accommodation and airfare: After you've nailed down your trip dates and duration, book the right Chester Gap holiday package for you.

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