Chester Gap Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

Top hotels in Chester Gap

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 2.555.544 ₫ per night from 14 Sept to 15 Sept
2.555.544 ₫
2.780.431 ₫ total
14 Sept - 15 Sept
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"The employees were friendly and courteous. Check in and check out went smoothly. The room was large and clean."

Reviewed on 17 Aug 2025

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, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
The price is 1.878.748 ₫ per night from 1 Sept to 2 Sept
1.878.748 ₫
2.091.046 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"Great location, clean, comfortable."

Reviewed on 13 Aug 2025

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
The price is 2.504.998 ₫ per night from 26 Aug to 27 Aug
2.504.998 ₫
2.725.438 ₫ total
26 Aug - 27 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"This is our 4th time staying here. Comfortable and ConvenientandAffordable"

Reviewed on 19 Aug 2025

Country Inn & Suites by Radisson, Winchester, VA
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 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.