Cheap flights to Hampshire County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Loading

Deals For This Weekend's Flights

Find The Perfect Hotel For After Your Flight

Score Epic Hampshire County Accommodation 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
$140 nightly
The price is $160 total per night from Aug 30 to Aug 31
$160 total
Aug 30 - Aug 31
Total with taxes and 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 ...
9/10 Wonderful! (1,645 reviews)
"The staff was knowledgeable and respectful. Kind and Helpful."

Reviewed on Jul 31, 2026

Opens in a new windowRocky Gap Casino & Resort
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Fully refundable
$90 nightly
The price is $100 total per night from Aug 30 to Aug 31
$100 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Opens in a new windowHoliday Inn Winchester Se-Historic Gateway by IHG
Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

3 out of 5
100 South George Street Cumberland MD
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $96 total per night from Aug 3 to Aug 4
$96 total
Aug 3 - Aug 4
Total with taxes and 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 ...
Opens in a new windowRamada by Wyndham Cumberland Downtown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from Aug 9 to Aug 10
$138 total
Aug 9 - Aug 10
Total with taxes and 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 ...
Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Hampshire County

Start your search for cheap flights to Hampshire County on Orbitz. Orbitz is where you will discover guaranteed low prices on Hampshire County flights, as well as all of the following conveniences:

Travel Updates on Your Mobile Device

Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Hampshire County flights. You can also review and reserve hotel rooms for when your Hampshire County flights land and see other special offers.

Low Prices Guaranteed on Flights to Hampshire County

Orbitz offers large discounts on a wide range of Hampshire County flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Hampshire County while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Hampshire County to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Hampshire County. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

Frequently asked questions

Which airlines fly to Hampshire County?
Have a look at the deals from the airlines that offer flights to Hampshire County. Whether you'd like to sip Champagne in first class or save cash in economy, there'll be a seat for you. Make your way to Washington Dulles Intl. Airport (IAD) with one of these reputable carriers:

  • United Airlines - 442 flights to Hampshire County per month
  • Air Canada - 86 flights to Hampshire County per month
  • Avianca - 73 flights to Hampshire County per month

How much is a flight to Hampshire County?
Plenty of fabulous deals were up for grabs this week, with round-trip flights to Hampshire County ranging from to . But it was passengers flying in from () who landed the best bargains. One-way flights to Hampshire County started from a low .
How to book the cheapest flight to Hampshire County?
Picking up cheap flights to Hampshire County is as easy as booking your ticket with Orbitz. But if you'd like to make sure you're grabbing the best flight deals around, here are some suggestions to follow:

  • Consider taking off from or landing at alternative airports for a cheaper fare. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will list your options, if any.
  • If your travel plans aren't cast in stone, click on the 'Show flexible dates' link to scan the flight deals for a range of departure dates. Go with any suitable cheaper fare that pops up.
  • Select 'Show options' to fine tune your search results. You can choose your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you want to fly in the morning, afternoon or evening.
  • Reserve your fare as soon as you've worked out your travel dates. While it does happen on occasion, tickets rarely get cheaper as your departure date gets closer.
  • Think about bundling your flights, hotels and car rental into a package deal to make your dollar go further.
  • Flying during the busy season means expensive airfares. Try to avoid traveling over popular dates, such as Easter, Thanksgiving and school breaks.

What is the best time to book a flight to Hampshire County?
On average, the cheapest month to purchase a plane ticket is in January. This is closely followed by February then August. When looking for a cheap flight to Hampshire County, it always pays to be ready to book. Cheap deals appear suddenly and don't hang around!
What day of the week is the cheapest to book a flight to Hampshire County?
When it comes to cheap fares to Hampshire County, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. A rewarding flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Hampshire County?
Based on Orbitz data from 2020, Monday is usually the best day to get cheap flights to Hampshire County. Tuesday also offers wallet-friendly fares, whereas Saturday has the most expensive ticket prices. Even though leaving at the weekend is often more convenient, you'll have more cash to play with if you set off at the start of the week.
What is the cheapest month to fly to Hampshire County?
Fly sometime in August if you're on a tight budget. Orbitz data has found that it's generally the best month for cheap flights to Hampshire County. June is when prices really go up.
Which airlines allow free cancellation?
We know that plans change and flexibility is important. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll find you fares more flexible than candy in a car on a hot day!
What do I need for the flight to Hampshire County?
Whether you're accustomed to flying or you're new to the skies, it helps to be organized when you travel. Here are several things to take into consideration:

  • Make sure you've packed your travel documents and some identification. For overseas trips, you'll need to take your passport. When purchasing your seats, always use the same name, gender and birth date as stated on your current ID.
  • A properly packed carry-on bag is the key to a comfortable flight experience. Given your flight to Hampshire County is no quick hop, take some snacks and activities to keep you happy. Something to read or listen to will help pass the time.
  • Aircraft cabins can get quite cold. Even if you're flying during the peak of summer, make sure you bring an extra warm layer with you.

How do I get cheap first-class/business deals to Hampshire County?
If you think a business or first-class fare is out of your reach, you may want to think again. Here are just a few tips to help you find a premium flight to Hampshire County for a whole lot less:

  • Flexibility isn't just a yoga thing. Have some room to move around your travel dates so you can pick up cheaper airfares when a big sale comes along.
  • Budget airlines offer business-class seating at more affordable prices. Ditch the full-service carriers and go with one of these cheaper options.
  • Make the most of your airline's flight rewards program and upgrade your seat. You can also bid for an upgrade in an online auction if available.

What is the best time to go to Hampshire County?
If you want to immerse yourself in the culture of Hampshire County in the busy season, April, May and September are the best months to visit. June 20 marks the onset of summer in the Northern Hemisphere and is a fantastic time to travel if you're fond of being outside. At this time of the year, average daily temperatures range from 55 ºF to 85 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.