Head Waters Vacations from $741

Book a Hotel + Flight or Car together to unlock savings

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 $792, price is now $741 per person
$741
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Weyers Cave (SHD)
8.2/10 Very Good! (983 reviews)
Great staff. Food in the restaurant was a great. We were able to check in early since our room was already available, although when we came down for breakfast we found out that their cook didn't show up so no breakfast. It happens, we did ask if we can get something from their store instead in lieu of the missing breakfast and they agreed.

Reviewed on Sep 29, 2025

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth

3.5 out of 5
Price was $1,025, price is now $921 per person
$921
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Weyers Cave (SHD)
9/10 Wonderful! (330 reviews)
Simply amazing definitely doing this again.

Reviewed on Sep 2, 2025

Iris Inn and Cabins

Iris Inn and Cabins

4 out of 5
Price was $1,069, price is now $986 per person
$986
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Weyers Cave (SHD)
8.8/10 Excellent! (3 reviews)
Every thing , extraordinary place .

Reviewed on Jul 22, 2025

Gibson's Warehouse

Gibson's Warehouse

3.5 out of 5
Price was $871, price is now $813 per person
$813
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Weyers Cave (SHD)
10/10 Exceptional! (177 reviews)
Amazing place to stay in Staunton. You will not be disappointed. Clean and comfortable with an amazing location.

Reviewed on Oct 10, 2025

Comfort Inn & Suites Harrisonburg

Comfort Inn & Suites Harrisonburg

2.5 out of 5
Price was $812, price is now $766 per person
$766
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,204 reviews)
On arrival at the Comfort Inn parking right in front of the hotel was available. Lobby was clean and tidy, gentleman behind the desk was friendly - girl was not. She looked up, we said hello and then proceeded to carry on looking at her phone. The gentleman checked us in and lwt us know about the amenities and where our room was. Room was clean, tidy and had a fridge, microwave and great tea and coffee facilities. A good stay overall.

Reviewed on Oct 12, 2025

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Head Waters Hotel Deals

Big Spring Bed & Breakfast

Big Spring Bed & Breakfast

Williamsville
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
2/10 (1 review)
"Nice quiet spot!"

Reviewed on Aug 17, 2025

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Healing Waters Cabin
Monterey Inn

Monterey Inn

4 out of 5
32 W Main St, Monterey, VA
$209 nightly
The price is $231 total per night from Nov 2 to Nov 3
$231 total
Nov 2 - Nov 3
Total with taxes and fees
9.4/10 Exceptional! (36 reviews)
"Terrific place Spotless comfortable lovely owners"

Reviewed on Sep 28, 2025

Monterey Inn
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.

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 $741 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.