Winchester Holidays from £678

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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.
Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Mount Vernon
per person
23 Sept - 29 Sept
found 24 hours ago
Return flight included
Glasgow (GLA) to Baltimore (BWI)
9.2/10 Wonderful! (864 reviews)
Room is a bit small not gonna lie, but the interior is very cool.

Reviewed on 2 Jul 2025

Canopy by Hilton Baltimore Harbor Point

Canopy by Hilton Baltimore Harbor Point

4 out of 5
Fells Point
per person
23 Sept - 29 Sept
found 24 hours ago
Return flight included
Glasgow (GLA) to Baltimore (BWI)
9/10 Wonderful! (1,005 reviews)
Nice property close to tons of stuff!

Reviewed on 4 Jul 2025

Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor

4 out of 5
Downtown West
per person
23 Sept - 29 Sept
found 24 hours ago
Return flight included
Glasgow (GLA) to Baltimore (BWI)
8.4/10 Very Good! (1,003 reviews)
Great amenities, huge pool, sauna and hot tub.

Reviewed on 23 Jun 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
per person
23 Sept - 29 Sept
found 24 hours ago
Return flight included
Glasgow (GLA) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
Terrible staff. So rude. I saw how they respond people and also their actitud terrible.

Reviewed on 30 Jun 2025

Baltimore Marriott Waterfront

Baltimore Marriott Waterfront

3.5 out of 5
Harbor East
per person
23 Sept - 29 Sept
found 24 hours ago
Return flight included
Glasgow (GLA) to Baltimore (BWI)
9.2/10 Wonderful! (1,009 reviews)
The worst Valet parking ever !! I needed to go get my car after 40 minutes waiting for it!

Reviewed on 2 Jul 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

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 £63 per night from 9 Jul to 10 Jul
£63
9 Jul - 10 Jul
includes taxes & fees
5.4/10 (1,000 reviews)
"Good environment and nice customer services"

Reviewed on 25 Jun 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 £82 per night from 3 Aug to 4 Aug
£82
3 Aug - 4 Aug
includes taxes & fees
7.8/10 Good! (1,011 reviews)
"Nice and friendly"

Reviewed on 2 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 £79 per night from 21 Jul to 22 Jul
£79
21 Jul - 22 Jul
includes taxes & fees
7.4/10 Good! (1,004 reviews)
"This hotel is very convenient if you are seeing a show at the Grand Ballroom which is right across the street. It was comfortable and clean and also affordable. The staff was friendly. Would recommend for a quick stopover in the downtown Wilmington area."

Reviewed on 2 Jul 2025

DoubleTree by Hilton Downtown Wilmington - Legal District
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

Beach Holidays

Beach Holidays

Family Friendly Holidays

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 £678. 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.