Chester Gap Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

  • Plan, book, travel with confidence

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

Your Chester Gap Holiday

Our holiday packages to Chester Gap let you customise 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 customised Chester Gap holiday on Expedia.

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

Top hotels in Chester Gap

Modern Mountain Retreat w/ Deck + Hot Tub!

Modern Mountain Retreat w/ Deck + Hot Tub!

Chester Gap, VA
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 26 Jun 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
The price is £78 per night from 7 Sept to 8 Sept
£78
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 £111 per night from 2 Sept to 3 Sept
£111
2 Sept - 3 Sept
includes taxes & 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 24 Aug 2025

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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chester Gap travel package cost?
From as low as , you can tailor make your Chester Gap package. Simply bundle hotels, flights and rental cars and be rewarded with discounts.
If I'm not able to travel, can I cancel my Chester Gap travel package?
Because we know life can throw you a few curveballs, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it without penalty. Your hotel, airline or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Chester Gap?
It's easy. Just bundle everything together. Hotels, rental cars and flights — combine whatever you need into a Chester Gap holiday package to save a ton of cash. Score even more deals when you include extras such as sightseeing tours to your booking. But that's not the only good part. You have the flexibility to customize your holiday your way. We offer over 550 air carriers and 1,000,000 properties worldwide, so that everyone has an opportunity to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Chester Gap holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a terrific getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip across multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is easier with this payment option. Put down a small deposit on your booking and then start working on your travel itinerary.

Where should I stay in Chester Gap?
If you aim to visit Rappahannock Cellars, skip commuting and find somewhere to stay nearby. It's one of the top attractions in this neighbourhood.
What are the top hotels in Chester Gap?
Get your trip off to a good start by booking a stay at White Moose Inn. It's one of most popular hotels in Chester Gap. Another top option is Belle Meade Bed And Breakfast.
How far in advance should I book my Chester Gap holiday?
While prices fluctuate, we generally recommend booking your spot as early as possible. Many international airfares become available on Expedia up to 12 months in advance. If you're booking late, you might still be in luck. Cheap journeys to Chester Gap sometimes occur just weeks before departure.
What does an Expedia Chester Gap travel package include?
It depends on what kind of trip you have in the works. Chester Gap holiday deals can include flights, hotels and car rentals. You can mix and match to find the bundle that suits your style and budget. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Chester Gap travel package?
Our prices are always low. However, you'll snap up even more savings when you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and a terrific range of choice.
Can I choose my airline with a Chester Gap Expedia travel package?
Yes — that's the beauty of an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines worldwide, so you have options galore when planning your Chester Gap adventure.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.