Chester Gap Vacations

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Photo by Brian V. Rowe

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Find the Best Chester Gap Vacation Packages

Chester Gap Hotel Deals

Modern Mountain Retreat w/ Deck + Hot Tub!
Modern Mountain Retreat w/ Deck + Hot Tub!
Chester Gap
9.8/10 Exceptional! (57 reviews)
Wonderful home-quiet yet convenient!
"My husband and I stayed in this home for our annual anniversary trip. We love hiking and brought our dog with us for some active relaxation. This home was one of the best we have stayed in. It had everything we needed, and was clean and comfortable. Conveniently located about 15 minutes from Front ..."

Reviewed on 13 May 2025

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Modern Mountain Retreat w/ Deck + Hot Tub!
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 AED 262 per night from Jun 9 to Jun 10
AED 262
AED 292 total
includes taxes & fees
9 Jun - 10 Jun
8/10 Very Good! (1,007 reviews)
"T"

Reviewed on 2 June 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AED 356 per night from Jun 11 to Jun 12
AED 356
AED 387 total
includes taxes & fees
11 Jun - 12 Jun
9.2/10 Wonderful! (1,004 reviews)
"A little off the beaten path but near enough to dining and shopping."

Reviewed on 30 May 2025

Comfort Inn & Suites
See all 485 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 vacation 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 vacation to Chester Gap costs.
What are the cheapest months to go to Chester Gap?
To pick up cheap Chester Gap vacation 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 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 vacation package as early as possible.
Is it cheaper to book a Chester Gap vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can customize 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 vacation 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 favorite 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 accommodations and airfare: After you’ve nailed down your trip dates and duration, book the right Chester Gap vacation package for you.