Chester Holidays from £826
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Your Chester Holiday
Reserve a Chester holiday package and get set to experience the best of this city. Consider basing yourself in the neighbourhood of Kent Narrows, which is good for cycling, views and nature. If your trip to Chester includes some sightseeing, check out renowned attractions like Chesapeake Bay Environmental Centre, Eastern Neck National Wildlife Refuge and Love Point State Park. Stop daydreaming and start doing. Browse the multitude of options on Expedia today and finally put your Chester holiday plans into gear!
Top Chester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Price was £1,096, price is now £826 per person
£826
per person
7 Jul - 12 Jul
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Great staff and a he beds were very comfortable
Reviewed on 21 Apr 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was £1,177, price is now £856 per person
£856
per person
7 Jul - 12 Jul
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9/10 Wonderful! (1,165 reviews)
Staff are lovely. Room was fine. Location is nice.
Reviewed on 30 Apr 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
Price was £1,322, price is now £980 per person
£980
per person
11 Jun - 15 Jun
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
They don’t tell you that parking is not close, in a creepy parking lot, paying $45+$8 (parking tax for overnight parking)+1(parker membership)=$54 per night to park. There is a cool food hall nearby but that’s about it. The hotel accepts pets to keep that in mind.
Reviewed on 28 Apr 2026
Kimpton Banneker Hotel by IHG
Downtown Washington D.C.
Price was £1,120, price is now £849 per person
£849
per person
7 Jul - 12 Jul
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9/10 Wonderful! (790 reviews)
The room I was in was a bit weird. the bed was in the middle of the room. and the lighting was very poor in the room mostly due to the way it was set up. I'd recommend they move the furniture around again cuz this was not working for them
Reviewed on 30 Apr 2026
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Population | 4,200 |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Sandy Point State Park, Sandy Point Beach and Matapeake State Park |
Top hotels in Chester
Waterfront Sunset Bayview: sleeps 6
Chester MD
10/10 Exceptional! (26 reviews)
We loved our stay at this gorgeous waterfront property in Chester! The home is clean and bright with many gathering spaces for our group of five. We really enjoyed spending time on the back porch on the comfy couches enjoying the beautiful view or sitting around the large dining table eating and ...
Reviewed on 21 Apr 2026
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
10/10 Exceptional! (126 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..
Reviewed on 14 Sept 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is £96 per night from 31 May to 1 Jun
£96
31 May - 1 Jun
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
We were in a room directly onto of the bar you could hear the music in our room. It was very annoying also the air conditioner was very loud.
Reviewed on 27 Apr 2026
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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* 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.
