Chester Gap Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

Ready to book your vacation to Chester Gap?

 

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Chester Gap Hotel Deals

Modern Mountain Retreat w/ Deck + Hot Tub!

Modern Mountain Retreat w/ Deck + Hot Tub!

Chester Gap
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 Jun. 26, 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 CA $135 per night from Sep 14 to Sep 15
CA $135
CA $147 total
Sep 14 - Sep 15
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"This location is always my overnight stop when traveling . Highly recommend."

Reviewed on Aug. 20, 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 CA $99 per night from Sep 1 to Sep 2
CA $99
CA $111 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
A night in Virginia
"Room was comfortable. The breakfast was decent. The Mexican restaurant attached is AMAZING. No conditioner and body wash was super low. I’m sure I could have gotten more if I asked but it was not a big deal. I did ask for more towels and they were quickly accommodating."

Reviewed on Aug. 19, 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chester Gap vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Chester Gap costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chester Gap?
To score cheap Chester Gap vacation packages, plan your trip outside of busy periods like public holidays and major events. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Chester Gap?
The ideal length for your Chester Gap vacation depends on what you'd like to do. Usually, a few days to a week will give you plenty of time to go to all the top attractions and explore some hidden gems along the way.
How to find the best Chester Gap package deals?
Use Expedia's filter tool to help you find some unbeatable Chester Gap package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Chester Gap package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Chester Gap vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a personalized Chester Gap vacation by choosing your preferred type of stay, airline and car class.
How to plan a trip to Chester Gap?

  1. Choose when to go: Check your diary and pack your bags. Your favourite time of year and the activities available will also help you decide when to escape to Chester Gap.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected costs that could arise during your trip to Chester Gap.
  3. Determine how many days away: Start by compiling a list of the sights and activities you'd like to get to in Chester Gap. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your dates and duration, lock in the right Chester Gap vacation package for you.

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