Head Waters Vacations from $280
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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.
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View all tripsHead Waters Hotel Deals
Big Spring Bed & Breakfast
Williamsville VA
10/10 Exceptional! (64 reviews)
"This is a great place to stay. House was clean and had everything we needed for our stay. The owners are very nice and even gave us tomatoes from their garden!I would definitely recommend this property to anyone looking for a place to stay in Highland County. The view from the front porch is ..."
Reviewed on Sep 1, 2026
Monterey Inn
32 W Main St Monterey VA
$195 nightly
$215 total
Sep 8 - Sep 9
Total with taxes and fees
9.4/10 Exceptional! (50 reviews)
"super friendly staff. whole experience was very chill."
Reviewed on Aug 25, 2026
Cabin By The Creek! Inground Pool! Spa!
Dayton VA
10/10 Exceptional! (34 reviews)
"What an amazing place! We really enjoyed our stay, even though it rained almost every day. The hot tub and the pool with the slide was the highlight, the Home was very warm and inviting, and the location was perfect."
Reviewed on Aug 19, 2026
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 $280 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.
