Hampshire County Vacation Packages

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Your Hampshire County Vacation

Book a vacation package to Hampshire County and make planning your adventure quick and easy. With the finer details taken care of before you leave, you can focus on enjoying every moment in this destination. If you're putting together a schedule of where to go during your trip to Hampshire County, top cities like Romney and Paw Paw should be included. Expedia has everything you need for planning your Hampshire County vacation. From hotels and flights, to activities and more, we know how to create a travel experience like no other.

Top vacation destinations in Hampshire County

WV Tunnel
FlightsFlightsHotelsHotels

Paw Paw

Paw Paw

Top Hampshire County Vacation Deals

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
just found
Roundtrip non-stop flight included
Montreal (YUL) to Martinsburg (MRB)
5.8/10 (306 reviews)
A bit pricey for the quality

Reviewed on Mar 24, 2026

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
just found
Roundtrip non-stop flight included
Montreal (YUL) to Martinsburg (MRB)
9.2/10 Wonderful! (430 reviews)
The history surrounding this place is fascinating. It was such a charming historic inn.

Reviewed on May 16, 2026

Hampshire County Hotel Deals

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

4 out of 5
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from May 25 to May 26
CA $123
CA $189 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,568 reviews)
"The spa was absolutely wonderful! I felt very pampered. The pool is wheelchair accessible and the pool area was very clean. The Lakeview Grille did a fabulous job serving our party of 11. Food was delicious and our server was top tier. The kids loved the cornhole and beach. We will absolutely go ..."

Reviewed on May 23, 2026

Rocky Gap Casino & Resort
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Jun 21 to Jun 22
CA $117
CA $133 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Everything was perfect. Easy to book, friendly staff , very clean and comfortable stay."

Reviewed on May 23, 2026

Spark by Hilton Winchester
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs WV
10/10 Exceptional! (62 reviews)
"Loved this cabin. Absolutely gorgeous area. Highly recommend."

Reviewed on Apr 13, 2026

Get rates
Dreamtime - Modern A-frame Cabin w/ Hot tub
See all 916 properties in Hampshire County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Frequently asked questions

How much does a Hampshire County vacation package cost?
Starting from as low as CA $817, a package is your ticket to cheaper travel. Put together your Hampshire County escape by choosing from our extensive range of hotels, airfares and rental cars.
How do I get a cheap travel package to Hampshire County?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Pick a combination that best fits you and watch your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotels from all over the world, which lets you customize your Hampshire County adventure.
What are the top hotels in Hampshire County?
For hotels in Romney with friendly service and cozy beds, look up Cozy Family Home With Kayaks, Dock And Fire Pit and Run Away To The Mountains Of Wv Peaceful Country Home Is Waiting For You. If you plan to explore Capon Bridge as well, you can look forward to a relaxing night's sleep at Glenstone Lodge or Country Inn & Suites by Radisson, Asheville Downtown Tunnel Road, NC.
How far in advance should I book my Hampshire County vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to 12 months prior to take off. This is typically the cheapest time to book. If circumstances have left you booking late, discount tickets to Hampshire County sometimes occur just a few weeks before departure.
What does an Expedia Hampshire County travel package include?
It comes down to what kind of trip you want to have. Hampshire County travel deals can include car rentals, flights and hotels. You can mix and match to find the travel package that suits your style and budget. You can also add on activities and experiences after you've booked to land even bigger discounts.
What should I know before booking a Hampshire County travel package?
A travel package can be customized for your circumstances and is a great way to make your money go further. How much you include is your call. Hotels, rental cars and flights — choose any combination that works with your plans.
Can I choose my airline with a Hampshire County Expedia vacation package?
You certainly can. We offer more than 550 airline partners worldwide, so choose the carrier that best suits your travel preferences.
If I'm not able to travel, can I cancel my Hampshire County vacation package?
Whether it's your hotel, flight or rental car, you can cancel or amend it. Locked in your Hampshire County vacation package in the last 24 hours? You may be able to make any changes for free. For bookings older than that, you may incur a fee from your hotel, airline or car rental company. For more information, browse our Customer Service Portal. We're here to help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.