Head Waters Vacation Packages

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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.

Top Head Waters Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Clarion Pointe Harrisonburg

Clarion Pointe Harrisonburg

2.5 out of 5
per person
Apr. 20 - Apr. 27
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Weyers Cave (SHD)
8.6/10 Excellent! (1,009 reviews)
This is a great hotel. It’s fairly quiet, and very clean. Room was a good size especially as we had our golden retriever with us. Bed is hard but we find most hotels are. There is a good free breakfast with lots of options. Lots of dining options close by as well. We appreciated them giving us a room on the main floor near an outdoor exit for taking our dog out. We have stayed here before and will continue to do so.

Reviewed on Feb. 27, 2025

Hotel 24 South

Hotel 24 South

3 out of 5
per person
Apr. 20 - Apr. 27
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,009 reviews)
The property is beautiful, excellent location.

Reviewed on Feb. 22, 2025

Wingate by Wyndham Waynesboro

Wingate by Wyndham Waynesboro

2.5 out of 5
per person
Apr. 25 - Apr. 28
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Weyers Cave (SHD)
8.6/10 Excellent! (763 reviews)
It was a great stay! Room was clean and breakfast was very good. The staff were very kind and provided us with what we needed.

Reviewed on Feb. 24, 2025

Skyline Motel By OYO Waynesboro US 250

Skyline Motel By OYO Waynesboro US 250

2 out of 5
per person
Apr. 25 - Apr. 28
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Weyers Cave (SHD)
No reviews
Super 8 by Wyndham Waynesboro

Super 8 by Wyndham Waynesboro

2 out of 5
per person
Apr. 25 - Apr. 28
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Weyers Cave (SHD)
7.4/10 Good! (841 reviews)
It’s one of the better Super 8’s that I’ve stayed in. The bed was comfy, pretty decent pillows, good size TV, and the staff was friendly and helpful.

Reviewed on Jan. 28, 2025

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Head Waters Hotel Deals

Big Spring Bed & Breakfast
Big Spring Bed & Breakfast
Williamsville
9.8/10 Exceptional! (56 reviews)
Lovely spot!
"Perfect for our needs and very clean! Really enjoyed our stay and will return."

Reviewed on Jan. 4, 2025

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Big Spring Bed & Breakfast
Simple. Rustic. Luxury.
Simple. Rustic. Luxury.
Monterey
9.8/10 Exceptional! (154 reviews)
Everything as advertised.
"Great communication and beautiful surroundings."

Reviewed on Dec. 30, 2024

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Simple. Rustic. Luxury.
Monterey Inn
Monterey Inn
4 out of 5
32 W Main St, Monterey, VA
The price is CA $270 per night from Mar. 31 to Apr. 1
CA $270
CA $298 total
includes taxes & fees
Mar 31 - Apr 1
9.6/10 Exceptional! (25 reviews)
"Clean & fresh; unique & retro; staffs very friendly & welcoming. Definitely to go back when we have chance"

Reviewed on Dec. 21, 2024

Monterey Inn
See all 93 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.

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Frequently asked questions

How much does a Head Waters vacation package cost?
You’ll find cheap prices from CA $792 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?
If you’re looking to book a cheap Head Waters vacation package, consider visiting in January, February and May. You’ll generally find lower rates on flights and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Head Waters?
With a well-organized itinerary, you can easily hit the main Head Waters sights in a handful of days. But if you prefer to discover hidden spots or take day trips, consider 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.
How to plan a trip to Head Waters?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to travel to Head Waters.
  2. Set a budget: Consider costs such as transportation, flights and meals when working out how much to set aside for your trip to Head Waters. Then, select a property that suits your budget, whether that’s an affordable stay or a lavish getaway.
  3. Set the duration of your trip: Start by listing all the sights and activities you’d like to experience in Head Waters. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Combine your airfare and accommodations: After you’ve settled on your dates and duration, book the perfect Head Waters 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.