COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Chester Gap, VA Vacation Packages

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Chester Gap Vacation: Coronavirus Information

Most Chester Gap hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Chester Gap trip, please visit our Coronavirus Information page (opens in new window).

Top Chester Gap Flight + Hotel Deals

The Westin Alexandria Old Town
WhyHotel Tysons Corner Greensboro Drive
Residence Inn by Marriott Washington, DC Downtown
Residence Inn by Marriott Washington Downtown/Convention Center
DC The Wharf Waterfront View Rentals

Top Hotels in Chester Gap

A mountain retreat, solitude for singles, a romantic getaway for couples...
A mountain retreat, solitude for singles, a romantic getaway for couples...
Front Royal, VA
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4.8/5Exceptional! (109 reviews)
Great weekend getaway
"Cozy cabin set on a wooded lot within a short walk to the AT. Stayed over during winter months. There was several inches of new snow on the ground, walkways and porch were clean and treated for ice when we arrived (thank you). No bugs or undesirables to worry about with a child wanting to play outdoors. ..."

Reviewed on Mar 31, 2021

A mountain retreat, solitude for singles, a romantic getaway for couples...
The Nest in Chester Gap
The Nest in Chester Gap
Front Royal, VA
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5/5Exceptional! (58 reviews)
We will be back!
"It was so beautiful and incredibly relaxing! We will definitely be back!"

Reviewed on Mar 12, 2021

The Nest in Chester Gap
New! Modern Mountain Retreat w/ Deck + Hot Tub!
New! Modern Mountain Retreat w/ Deck + Hot Tub!
Front Royal, VA
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5/5Exceptional! (3 reviews)
Cozy mountain house within walking distance of the AT
"I came here during the week to get out of the city for a few days. Bedrooms and bathrooms were all clean and appeared recently renovated. The coded door locks made it easy to get in when I arrived and was simpler than having to deal with keys and lockboxes. Great communication from the owners and ..."

Reviewed on Mar 17, 2021

New! Modern Mountain Retreat w/ Deck + Hot Tub!
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.

Top things to do in Chester Gap

Frequently asked questions

How much does a Chester Gap vacation package cost?
From as little as $656. Yes, you read that correctly. Our Chester Gap vacation packages are an awesome way to make your dollars go much further. Bundle your preferred hotels, flights and car rentals and get out and explore this lively destination.
If I'm not able to travel, can I cancel my Chester Gap vacation package?
You sure can, and we’re here to help. You may be able to amend or cancel your Chester Gap vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company for older bookings. If life gets in the way of your vacation, look up our Customer Service Portal for further information.
How do I get a cheap travel package to Chester Gap?
You can save as much as $583 if you bundle your hotels, car rentals and flights into a Chester Gap vacation package. Sometimes cheap packages mean fewer options. But that’s not the case with Expedia. We offer more than 550 air carriers and 1,000,000 properties all over the world, which means you’ll always have plenty of variety to choose from. Like to save even more? Add some exciting activities to your package deal and unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Chester Gap?
There’s so much to explore in Chester Gap, so spend your evenings close to its top sights and allow yourself more time sightseeing. Chester Gap Cellars is one place to add to your to-do list.
When is the best time of year to visit Chester Gap?
If saving on expenses is a priority, is the best time to take a break in Chester Gap. is typically the priciest month, so you’ll need a bigger travel budget if you visit then. are the high season months and when this destination is often at its most exciting. Alternatively, consider if you’d prefer a quieter vacation.
How far in advance should I book my Chester Gap vacation?
It’s difficult to pick the best time for airfares, but we usually say the earlier, the better. Many international journeys on Expedia become available to compare up to a year in advance. If you can’t book early, don’t fret. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Chester Gap travel package include?
Hotels, flights and a cool car for your road trip adventures. Simply choose your preferred bundle and get access to incredible deals. Once you’ve made your booking, add on some sightseeing tours and watch your savings grow. When it comes to planning your Chester Gap trip, you’re in charge!
What should I know before booking a Chester Gap travel package?
Find deals to match your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your escape. You’ll save precious dollars just by bundling your bookings. Whether you’re embarking on a skiing adventure or relaxing on a sunny beach, your dream vacation is only clicks away.
Does Expedia offer Book Now, Pay Later Chester Gap vacation packages?
If you’d rather split the cost of your hotel and activities over several payments, Expedia can help you out. Paying the total cost of your travel upfront isn’t always the best way to budget for your break, so we’ve teamed up with online lender Affirm to give you financial flexibility. Book Now, Pay Later and remove the stress of saving to travel.
Can I choose my airline with a Chester Gap Expedia vacation package?
Yes — that’s one of the best things about an Expedia package. You’re in control. We have access to more than 550 airline partners around the world, so you have lots of choice when putting together your Chester Gap adventure.