Chester Holidays from £1,001
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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.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was £1,308, price is now £1,001 per person
£1,001
per person
4 Aug - 9 Aug
found 22 hours ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
9/10 Wonderful! (1,177 reviews)
Everything was perfect, a very nice surprise.
Reviewed on 8 May 2026
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Price was £1,785, price is now £1,273 per person
£1,273
per person
18 Jun - 25 Jun
found 1 day ago
Return direct flight included
Birmingham (BHX) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Great staff and a he beds were very comfortable
Reviewed on 21 Apr 2026
Lyle Washington D.C.
Northwest
Price was £1,554, price is now £1,174 per person
£1,174
per person
18 Jun - 25 Jun
found 1 day ago
Return direct flight included
Birmingham (BHX) to Baltimore (BWI)
9.4/10 Exceptional! (1,682 reviews)
We absolutely loved the Lyle Hotel. Our room was very comfortable with so many well thought out details. The interior design was unique and beautiful. We also loved the neighborhood and location. This is definitely the place to stay in DC!
Reviewed on 10 May 2026
Riggs Washington DC
Downtown Washington D.C.
Price was £2,160, price is now £1,672 per person
£1,672
per person
18 Jun - 25 Jun
found 1 day ago
Return direct flight included
Birmingham (BHX) to Baltimore (BWI)
9.4/10 Exceptional! (1,442 reviews)
We were welcomed with a glass of champagne or rose. Our room was comfortable and delightfully decorated, including thoughtful and useful items like an umbrella and tote bag. We ordered a quick dinner in Cafe Riggs. The portions were generous and the food was delicious. Staff was attentive and very friendly.
Reviewed on 10 May 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
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is £129 per night from 31 May to 1 Jun
£129
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (1,858 reviews)
The staff were fabulous and our room was wonderful.
Reviewed on 12 May 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.
