Head Waters Vacations from $759

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Your Head Waters Vacation

Excellent adventures await when you lock in a Head Waters vacation package. Whether you're a foodie, history enthusiast or just a traveler who loves discovering new places, there's something for everyone in this lively city. Eager to sightsee? Spend your days enjoying popular attractions such as Sugar Tree Country Store during your trip to Head Waters. Whatever your travel plans or the size of your budget, putting together a tailored Head Waters vacation is a breeze with Expedia.

The Latest Head Waters vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $915, price is now $759 per person
$759
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Weyers Cave (SHD)
8.2/10 Very Good! (1,002 reviews)
Expected breakfast to be included like all the others

Reviewed on Nov 8, 2025

Waynesboro Home Near Wintergreen Charlottesville

Waynesboro Home Near Wintergreen Charlottesville

2 out of 5
Price was $2,154, price is now $1,774 per person
$1,774
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Weyers Cave (SHD)
No reviews
Iris Inn and Cabins

Iris Inn and Cabins

4 out of 5
Price was $1,838, price is now $1,526 per person
$1,526
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Weyers Cave (SHD)
9.6/10 Exceptional! (7 reviews)
Incredible Mountain View at Sunset. Extremely comfortable bed. Delicious breakfast.

Reviewed on Nov 6, 2025

Gibson's Warehouse

Gibson's Warehouse

3.5 out of 5
Price was $1,233, price is now $1,032 per person
$1,032
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Weyers Cave (SHD)
9.8/10 Exceptional! (184 reviews)
Absolutely phenomenal stay. Easy check in, clean and spacious. This will be our go to for vacation each year!!

Reviewed on Dec 8, 2025

Massanutten Resort

Massanutten Resort

2.5 out of 5
Price was $1,130, price is now $952 per person
$952
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Weyers Cave (SHD)
8/10 Very Good! (1,093 reviews)
My stay was fabulous the staff was great and my room was excellent

Reviewed on Dec 5, 2025

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Head Waters Hotel Deals

Big Spring Bed & Breakfast

Big Spring Bed & Breakfast

Williamsville VA
9.8/10 Exceptional! (59 reviews)
A perfect get away if you are in need of some peace and quiet and a break from the hustle and bustle of the city. Absolutely beautiful!!

Reviewed on Jun 18, 2025

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Big Spring Bed & Breakfast
Healing Waters Cabin

Healing Waters Cabin

Doe Hill VA
6/10 (2 reviews)
Nice quiet spot!

Reviewed on Aug 17, 2025

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Healing Waters Cabin
Simple. Rustic. Luxury.

Simple. Rustic. Luxury.

Monterey VA
9.8/10 Exceptional! (172 reviews)
Wood burning fireplace was vreat!! Loved the vibesand serenity. Thank you!

Reviewed on Nov 16, 2025

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Simple. Rustic. Luxury.
See all 96 properties in Head Waters
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.

Find the Best Head Waters Vacation Packages

Head Waters Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Head Waters vacation package cost?
You'll find cheap prices from $759 on Expedia for your Head Waters getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Head Waters costs.
What are the cheapest months to go to Head Waters?
November, December and January are great times to search for cheap Head Waters vacation packages. Traveling in quieter periods means you can typically find better prices on accommodations and flights.
How many days is enough for Head Waters?
With a well-planned schedule, you can easily hit the most popular Head Waters sights in a handful of days. But if you want to explore off the beaten track or go on day tours, think about booking your Head Waters vacation for longer.
How to find the best Head Waters package deals?
Use Expedia's filters to find some great Head Waters package deals. When you start 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 browse for Head Waters package deals in the off-season. Switch up your travel dates and you may land 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 Head Waters vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Head Waters vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Head Waters?
If you're considering a spur-of-the-moment Head Waters adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Head Waters vacation packages?
If you're like us, you love discovering new places but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Head Waters trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.