Hampshire County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Hampshire County

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

3 out of 5
16701 Lakeview Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,300 reviews)
"Simple nature and a beautiful surrounding with plenty to keep a weekend full or relaxed. Great quick getaway. Beauty and nature walk in the hills and around the lake were perfect."

Reviewed on 25 Sept 2025

Get rates
Rocky Gap Casino & Resort
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is 2.322.804 ₫ per night from 5 Oct to 6 Oct
2.322.804 ₫
2.631.738 ₫ total
5 Oct - 6 Oct
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"We needed a break with a long family care situation. We took a break and stayed in Winchester and relaxed. Hampton Inn was just perfect. Breakfast was great! Thank you!"

Reviewed on 28 Sept 2025

Hampton Inn Winchester-University/Mall Area
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is 2.859.709 ₫ per night from 5 Oct to 6 Oct
2.859.709 ₫
3.111.363 ₫ total
5 Oct - 6 Oct
includes taxes & fees
9.2/10 Wonderful! (2,166 reviews)
"Friendly front desk..needed additional pillow and blanket ..got immediate response"

Reviewed on 23 Sept 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 877 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.

Frequently asked questions

How much does a Hampshire County holiday package cost?
Starting from as low as , 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 1null000null000 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 cosy beds, look up Cosy 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 holiday?
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 holiday 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 holiday package?
Whether it's your hotel, flight or rental car, you can cancel or amend it. Locked in your Hampshire County holiday 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.