Winchester Holidays from £1,024

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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.
The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
Price was £1,366, price is now £1,024 per person
£1,024
per person
3 Jul - 10 Jul
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
great facility and location in the heart of AdamsMorgan! Love the spacious and comfy coffee shop, perfect for working or socializing! Staff were helpful and professional!

Reviewed on 15 Apr 2026

The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
Price was £1,610, price is now £1,121 per person
£1,121
per person
3 Jul - 10 Jul
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
8.8/10 Excellent! (1,341 reviews)
The stuffs are very friendly and helpful. The gym is great.

Reviewed on 14 Apr 2026

The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Northwest
Price was £1,591, price is now £1,140 per person
£1,140
per person
18 May - 25 May
found 1 day ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
8.6/10 Excellent! (1,458 reviews)
Staff as very helpful. There was some refurbishments happening during our stay and they were very accommodating. Room was spacious. Bed was very comfortable.

Reviewed on 13 Apr 2026

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Price was £1,869, price is now £1,340 per person
£1,340
per person
23 May - 28 May
found 1 day ago
Return direct flight included
London (LHR) to Baltimore (BWI)
9.4/10 Exceptional! (1,094 reviews)
Room and bathroom lovely. But dining is limited. No true dining area. off the lobby

Reviewed on 4 Apr 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was £1,427, price is now £1,074 per person
£1,074
per person
23 Jun - 28 Jun
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.4/10 Exceptional! (1,417 reviews)
Great historic property with a very helpful, friendly, and professional staff. Well done!

Reviewed on 15 Apr 2026

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

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
Fully refundableReserve now, pay when you stay
The price is £57 per night from 24 Apr to 25 Apr
£57
24 Apr - 25 Apr
includes taxes & fees
5.6/10 (1,001 reviews)
There’s black mold all over the windowsills and I even took pictures. The card keys don’t work so every time you need to go up in the elevator and every time you need to get in your room, you have to go to the front desk and physically have the person from the front desk. Let you up the elevator ...

Reviewed on 15 Apr 2026

Quality Inn Newark - Wilmington
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
Fully refundableReserve now, pay when you stay
The price is £164 per night from 22 Apr to 23 Apr
£164
22 Apr - 23 Apr
includes taxes & fees
8.8/10 Excellent! (201 reviews)
Oh yea !, had a amazing stay I’ll be back verybsoon

Reviewed on 12 Apr 2026

Great Wolf Lodge Perryville
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 £76 per night from 19 Apr to 20 Apr
£76
19 Apr - 20 Apr
includes taxes & fees
7.6/10 Good! (1,237 reviews)
Yes yes very clean

Reviewed on 11 Apr 2026

Sonesta Select Newark Christiana Mall
See all 578 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.
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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

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* 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.