Winchester Holidays from £574

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Your Winchester Holiday

History, cuisine, art and more … There's so much to discover with a Winchester holiday package. And with the ability to customise your city break, it's guaranteed to be one you won't forget. Eager to start exploring your surroundings? Fair Hill State Natural Resources Management Area, Patriots Glen Golf Club and East Meadow Park are among the leading places to visit during your trip to Winchester. Your dream Winchester holiday is a couple of clicks away. Search accommodation, flights and more on Expedia for an adventure that's tailored to suit your style.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Days Inn & Suites by Wyndham Laurel Near Fort Meade

Days Inn & Suites by Wyndham Laurel Near Fort Meade

2 out of 5
North Laurel
Price was £631, price is now £574 per person
£574
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LHR) to Baltimore (BWI)
7/10 Good! (1,004 reviews)
Me fascinó la atención la comodidad las camas muy cómodas y todo muy cómodo para un descanso

Reviewed on 14 Aug 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Price was £853, price is now £636 per person
£636
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LHR) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
This is definitely not four stars facility. More like two and half. Our stay for one night was ok. Sheets were clean. Fridge was missing in the cabinet in our room.

Reviewed on 14 Aug 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Price was £1,052, price is now £909 per person
£909
per person
30 Oct - 2 Nov
found 13 hours ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
Every boat show this is my go to spot.

Reviewed on 17 Aug 2025

Metro Points Hotel

Metro Points Hotel

3 out of 5
Price was £751, price is now £652 per person
£652
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LHR) to Baltimore (BWI)
7.4/10 Good! (1,362 reviews)
Second time here Great bang for the buck

Reviewed on 16 Aug 2025

The Westin Annapolis

The Westin Annapolis

4 out of 5
Price was £1,000, price is now £893 per person
£893
per person
30 Oct - 2 Nov
found 13 hours ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
8.6/10 Excellent! (1,005 reviews)
Bed was extremely comfortable. The Westin had great food at very reasonable prices.

Reviewed on 18 Aug 2025

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 West Meadow Park

Top hotels in Winchester

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 £83 per night from 26 Aug to 27 Aug
£83
26 Aug - 27 Aug
includes taxes & fees
7.8/10 Good! (1,078 reviews)
"I’ve stayed here multiple times in this last time was probably the best. The staff was very helpful and courteous, and the amenities were top-notch."

Reviewed on 18 Aug 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 £70 per night from 31 Aug to 1 Sept
£70
31 Aug - 1 Sept
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"I love the location. Will definitely stay again."

Reviewed on 16 Aug 2025

DoubleTree by Hilton Downtown Wilmington - Legal District
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 £55 per night from 24 Aug to 25 Aug
£55
24 Aug - 25 Aug
includes taxes & fees
5.4/10 (1,000 reviews)
"It’s a nice place to sleep if you looking for a quiet place clean and nice staff"

Reviewed on 12 Aug 2025

Red Roof Inn & Suites Newark - University
See all 616 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
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Beach Holidays
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Family Friendly Holidays

Popular places to visit

Elkton Golf and Batting Center

You can take time to visit Elkton Golf and Batting Center during your travels to Elkton. While you're here, you can savour the top-notch restaurants.

Elkton Golf and Batting Center

Frequently asked questions

How much does a Winchester travel package cost?
Custom build your Winchester travel package from just £574. Pick from any combination of rental cars, flights and hotels to build the trip you've been dreaming of. Remember to add on a few experiences or tours!
If I'm not able to travel, can I cancel my Winchester travel package?
Because we know life can be unpredictable, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've booked your Winchester travel package in the last 24 hours, you may be able to change or cancel it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
How do I get a cheap travel package to Winchester?
Creating your own Winchester holiday package with Expedia is a smart way to save. We offer access to over 550 air carriers and 1,000,000 hotels around the globe. With such a wonderful range to choose from, you'll have no issues putting together your dream trip.
Does Expedia offer Book Now, Pay Later Winchester holidays?
We do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply choose the payment plan that suits best during checkout and take away the stress of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying bite-sized amounts each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan from Klarna.

What are the top hotels in Winchester?
Lock in a room at Motel 6 Elkton, MD. It's one of this area's most in-demand hotels. Another top-rated option in Winchester is La Quinta Inn & Suites by Wyndham Newark - Elkton.
How far in advance should I book my Winchester holiday?
It depends on the air carrier, but you can usually compare international fares on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky travellers occasionally find a cheaper ticket just weeks before departure dates.
What does an Expedia Winchester travel package include?
Flights, hotels and rental cars, or any combination of them — it's your choice. Whether you're headed to Winchester on a family road trip or travelling solo, there's a bundle to match your budget and style. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Winchester travel package?
Our prices are already low. However, you'll snap up even more savings if you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Winchester Expedia travel package?
Yes, you're in charge. We offer more than 550 partner airlines around the world, so you can customize your Winchester holiday according to your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.