Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Winchester Holiday

The lively city of Winchester is calling. Delve into everything from its highlights to its hidden gems with a Winchester holiday package that's customised to you. A trip to Winchester is a terrific opportunity to take in the sights. Check out well-known attractions like Fair Hill State Natural Resources Management Area, Historical Society of Cecil County and East Meadow Park. A few quick clicks is all it takes to craft your perfect Winchester holiday on Expedia.

Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Wilmington, DE (ILG-New Castle)
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Historical Society of Cecil County, Fair Hill State Natural Resources Management Area and East Meadow Park

Our pick of the best Winchester Hotel Deals

Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

2 out of 5
1119 S College Avenue, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$131 per night from 20 July to 21 July
AU$131
20 July - 21 July
includes taxes & fees
5.4/10 (1,011 reviews)
"Good stop over a little construction"

Reviewed on 5 Jul. 2025

Red Roof Inn & Suites Newark - University
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 3 Aug to 4 Aug
AU$172
3 Aug - 4 Aug
includes taxes & fees
7.8/10 Good! (1,031 reviews)
"Very friendly and helpful staff!"

Reviewed on 14 Jul. 2025

Sonesta Select Newark Christiana Mall
DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

4 out of 5
700 N King St, Wilmington, DE
Fully refundableReserve now, pay when you stay
The price is AU$165 per night from 30 July to 31 July
AU$165
30 July - 31 July
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"Had a great stay! The room was clean and comfortable, the staff were friendly, and the location was perfect. Would definitely stay here again!"

Reviewed on 11 Jul. 2025

DoubleTree by Hilton Downtown Wilmington - Legal District
See all 613 properties in Winchester
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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Discover the most popular places to visit in Winchester

Historical Society of Cecil County

You can spend time exploring the galleries in Historical Society of Cecil County during your travels in Elkton. While you're here, you can savour the top-notch restaurants.

Historical Society of Cecil County

West Meadow Park

Explore the great outdoors at West Meadow Park, a lovely green space in Elkton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

West Meadow Park

Frequently asked questions

How much does a Winchester holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchester?
You're likely to find lower prices and greater availability in January, February and November. Browse our cheap Winchester holiday packages and you could land some great off-season discounts.
How many days is enough for Winchester?
Usually, a handful of days is enough to tick off the top attractions during your Winchester holiday. However, if you prefer to have more time to rest or go on day trips, think about extending your itinerary.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester escape underway.
Is it cheaper to book a Winchester holiday as a package?
You can enjoy significant savings on your Winchester break by booking a tailored holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Winchester?
If you have your Winchester holiday dates confirmed, book as early as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Winchester?

  1. Choose your dates: What you plan to do in Winchester and your favourite season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Winchester.
  3. Decide how long to go for: Now that you know more about Winchester, you can work out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Winchester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.