Book Exclusive Hampshire County Vacation Packages

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Hampshire County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
Price was CA $883, price is now CA $817 per person
CA $817
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Martinsburg (MRB)
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Cedar Creek and Belle Grove National Historical Park and Belle Grove Plantation are located nearby.
Wayside Inn

Wayside Inn

3.5 out of 5
Price was CA $1,149, price is now CA $1,055 per person
CA $1,055
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Martinsburg (MRB)
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Cedar Creek and Belle Grove National Historical Park and Cedar Creek Battlefield Foundation are located nearby.

Top Hampshire County hotels deals

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

4 out of 5
16701 Lakeview Road NE Cumberland MD
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
CA $189 total
May 26 - May 27
includes taxes & fees
Book a stay at this spa hotel in Cumberland. Enjoy free parking, an outdoor pool, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rocky Gap Casino and Golf Course and Lake Habeeb Beaches are located nearby.
Pool
Hot tub
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $105 per night
CA $105
CA $119 total
Jun 21 - Jun 22
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Abram's Delight and Apple Blossom Mall are located nearby.
Breakfast included
Pet-friendly
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs WV
Get rates
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa are located nearby.
Hot tub
Kitchen
Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

3 out of 5
100 South George Street Cumberland MD
Free cancellation
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
CA $133 total
May 27 - May 28
includes taxes & fees
Book a stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Downtown Cumberland Historic District and Allegany Museum are located nearby.
Breakfast included
Pet-friendly
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $146 per night
CA $146
CA $159 total
Jun 2 - Jun 3
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rutherford Crossing and Star Fort Civil War Battlefield are located nearby.
Pool
Breakfast included
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $169 per night
CA $169
CA $191 total
Jun 7 - Jun 8
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Court House Civil War Museum and Bright Box Theater are located nearby.
Pool
Spa
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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.

Photos of local treasures

Browse Hampshire County vacation photos for more inspiration

An old vintage train with thick black smoke making its way through the forest in West Virginia, with beautiful fall colors and foliage. Shot near Cass, WV, USA.

Frequently asked questions

How much are vacation packages to Hampshire County?
Travelocity offers flight and hotel vacation packages from just CA $817. With such amazing bargains, you'll be exploring all of Hampshire County before long.
Where can I get the best vacation package deals for Hampshire County?
No matter what you enjoy doing, Travelocity can help you find a great Hampshire County package deal. All you have to do is select a combination from our 400 airlines and 1,000,000 properties across the globe.
Why should I purchase my Hampshire County vacation bundle with Travelocity?
With our Price Match Guarantee, we'll match any cheaper price you're able to find. Add to that our 24/7 customer support and top-quality service and your dream vacation is well within reach.
Can I save on my Hampshire County car rental if I book it with my hotel or flight?
Combining your bookings into a Hampshire County vacation package will save you some serious money. You can book a flight and car; a flight, hotel and car; or a hotel and car. You won't find a better way to discover the greater Hampshire County area than with your own set of wheels. You can also add activities and experiences to your Travelocity package.
Which airport is best for Hampshire County?
Most Hampshire County travelers land at Hagerstown Regional Airport (HGR).
What is there to do in Hampshire County?
A well-known attraction you won't want to miss in Hampshire County is Potomac Eagle Scenic Railroad. After you've crossed that off, spend time meeting the locals and discovering the character of this exciting destination.