Deals on vacations and trips to Head Waters

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Head Waters flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn

Comfort Inn

2.5 out of 5
Price was $353, price is now $322 per person
$322
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Weyers Cave (SHD)
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

2.5 out of 5
Price was $378, price is now $356 per person
$356
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Weyers Cave (SHD)
This hotel features an indoor pool and a gym. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $351, price is now $335 per person
$335
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Weyers Cave (SHD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $429, price is now $413 per person
$413
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Weyers Cave (SHD)
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a picnic area and multilingual staff can provide around-the-clock assistance.
Massanutten Resort

Massanutten Resort

2.5 out of 5
Price was $440, price is now $426 per person
$426
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Weyers Cave (SHD)
This hotel features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy snowboarding. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities.

Top Head Waters hotels deals

Big Spring Bed & Breakfast

Big Spring Bed & Breakfast

Williamsville VA
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Stay at this vacation home in Head Waters. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attraction Sugar Tree Country Store is located nearby.
Kitchen
Pet friendly
Healing Waters Cabin

Healing Waters Cabin

Doe Hill VA
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This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
Simple. Rustic. Luxury.

Simple. Rustic. Luxury.

Monterey VA
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A hot tub is featured at this cabin, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
~ Cabin in the Wildwoods ~ Secluded ~ Rustic ~ Family Friendly~

~ Cabin in the Wildwoods ~ Secluded ~ Rustic ~ Family Friendly~

Franklin WV
$176 nightly
The price is $196 total per night
$196 total
Dec 21 - Dec 22
Total with taxes and fees
This cabin includes a garden and barbecue grills.
Monterey Inn

Monterey Inn

4 out of 5
32 W Main St Monterey VA
$209 nightly
The price is $231 total per night
$231 total
Dec 14 - Dec 15
Total with taxes and fees
This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. Concierge services are provided for your convenience.
Parking included
Free WiFi
Dog-friendly, riverfront home with games galore, pool, & mountain view

Dog-friendly, riverfront home with games galore, pool, & mountain view

McDowell VA
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An indoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.
Don't see what you're looking for?
See all available properties in Head Waters
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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 are vacation packages to Head Waters?
You'll be pleasantly surprised — you could find yourself in Head Waters for a mere $322. At Travelocity, we save you money and stress with our vacation packages. With experiences, hotels and flights all ready to be snapped up, what's holding you back?
Where can I get the best vacation package deals for Head Waters?
It's simple — browse Travelocity. With no less than 400 partner airlines and 1,000,000 properties around the world, it's easy to craft a Head Waters package deal that satisfies your wanderlust.
Why should I purchase my Head Waters vacation package via Travelocity?
Because you'll never roam alone if you book with us, and we offer round-the-clock customer support and excellent service to boot. Add to that our Price Match Guarantee and a massive range of experiences to pick from. It's our job to make your daydreams a reality.
Can I save money on my Head Waters car rental if I combine it with a hotel or flight?
With a Head Waters vacation package, you can combine your car, flight and hotel bookings and save tons. If you want to discover the best of this wonderful area, why not make a beeline for Monticello? This popular attraction is 55 mi from Head Waters. With your own rental car, you'll be there belong long.
Which airport is best for Head Waters?
Head Waters has a couple of airports to choose from — Charlottesville-Albemarle Airport (CHO) (55 mi away from the city center) and Shenandoah Valley Regional Airport (SHD) (30 mi away from central Head Waters).
Where should I stay when visiting Head Waters?
If you're searching for somewhere to spend your nights, take a look at the Big Spring Bed & Breakfast. It's the top pick for many visitors.

Photos of local treasures

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