Deals on vacations and trips to Head Waters

Save when you book Head Waters package deals

Choose two or more items and save on your trip:

Head Waters flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Massanutten Resort by Tripforth

Massanutten Resort by Tripforth

3 out of 5
Price was $557, price is now $526 per person
$526
per person
Apr 4 - Apr 7
found 14 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Weyers Cave (SHD)
A full-service spa and an outdoor pool are featured at this smoke-free vacation home. Enjoy the indoor pool and perks like free self parking and free WiFi. There's a gym and multilingual staff can provide around-the-clock assistance.
Waynesboro Home Near Wintergreen Charlottesville

Waynesboro Home Near Wintergreen Charlottesville

2 out of 5
Price was $1,702, price is now $1,561 per person
$1,561
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Weyers Cave (SHD)
This vacation home features free WiFi in public areas, a garden, and barbecue grills.
Massanutten's Regal Vistas by Tripforth

Massanutten's Regal Vistas by Tripforth

3.5 out of 5
Price was $1,081, price is now $1,010 per person
$1,010
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Weyers Cave (SHD)
This vacation home features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Multilingual staff can provide around-the-clock assistance and barbecue grills are on offer.
The Summit at Massanutten Resort by Tripforth

The Summit at Massanutten Resort by Tripforth

3.5 out of 5
Price was $900, price is now $850 per person
$850
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) to Weyers Cave (SHD)
An outdoor pool is featured at this vacation home, along with free self parking. Enjoy the indoor pool and perks like free WiFi. A gym is also provided.
Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $885, price is now $836 per person
$836
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Portland (PWM) 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.

Top Head Waters hotels deals

Big Spring Bed & Breakfast

Big Spring Bed & Breakfast

Williamsville VA
Get rates
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.
Healing Waters Cabin

Healing Waters Cabin

Doe Hill VA
Get rates
This cabin featured laundry facilities 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
Feb 19 - Feb 20
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.
Simple. Rustic. Luxury.

Simple. Rustic. Luxury.

Monterey VA
Get rates
A hot tub is featured at this cabin, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
Hot Tub
Kitchen
On farm cottage with mountain views.

On farm cottage with mountain views.

Bridgewater VA
$163 nightly
The price is $181 total per night
$181 total
Feb 19 - Feb 20
Total with taxes and fees
This cottage features a garden, laundry facilities, and barbecue grills.
~ Cabin in the Wildwoods ~ Secluded ~ Rustic ~ Family Friendly~

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

Franklin WV
$181 nightly
The price is $201 total per night
$201 total
Feb 19 - Feb 20
Total with taxes and fees
This cabin includes a garden and barbecue grills.
Don't see what you're looking for?
See all available properties in Head Waters
View all properties
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 $526. 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

Browse Head Waters vacation photos for more inspiration