Chester Holidays from £1,008

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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.
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Price was £1,397, price is now £1,008 per person
£1,008
per person
9 Sept - 16 Sept
found 9 hours ago
Return direct flight included
London (LON) to Baltimore (BWI)
8.4/10 Very good! (1,002 reviews)
Expected better from crown plaza

Reviewed on 30 Jun 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £2,496, price is now £1,661 per person
£1,661
per person
14 Sept - 21 Sept
found 1 day ago
Return direct flight included
London (LGW) to Baltimore (BWI)
9/10 Wonderful! (1,199 reviews)
Definitely think this hotel should be labeled 3 or 4 stars instead of 5. How wore down it looks in like the elevators and certain places. Staff super friendly though! Love free the coffee and unique selection of teas but that area was always quite messy and no trash can to throw away items in that area even though I brought it to their attention prior that the trash can was missing.. not sure if its worth 40 dollar a day amenity fee prob wont stay at this location in the future

Reviewed on 1 Jul 2026

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
Price was £2,587, price is now £1,750 per person
£1,750
per person
2 Aug - 9 Aug
found 2 hours ago
Return direct flight included
Edinburgh (EDI) to Baltimore (BWI)
9.4/10 Exceptional! (1,106 reviews)
My stay was everything I could have imagined. The staff were extremely friendly and attentive. Hospitality was 10 out of 10. The spa services were amazing. Would definitely stay here again.

Reviewed on 2 Jul 2026

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Price was £1,568, price is now £1,106 per person
£1,106
per person
14 Sept - 21 Sept
found 1 day ago
Return direct flight included
London (LGW) to Baltimore (BWI)
8.8/10 Excellent! (1,901 reviews)
It was a good stay, parking around the corner and breakfast at a restaurant across the street

Reviewed on 2 Jul 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was £1,510, price is now £1,120 per person
£1,120
per person
14 Sept - 21 Sept
found 1 day ago
Return direct flight included
London (LGW) to Baltimore (BWI)
8.8/10 Excellent! (1,001 reviews)
The air-conditioning was very loud. There is no central airflow. The indoor unit is very loud, it is very difficult to sleep next to it. Also we were on the top floor near the elevator, it was very noisy, there was constant noise.

Reviewed on 28 Jun 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

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is £103 per night from 14 Jul to 15 Jul
£103
14 Jul - 15 Jul
includes taxes & fees
9/10 Wonderful! (1,866 reviews)
"The staff was very friendly. The room was clean."

Reviewed on 2 Jul 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is £82 per night from 5 Jul to 6 Jul
£82
5 Jul - 6 Jul
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Check in was smooth, typical. Room was located on a wing away from the lobby which we liked b/c we could access directly from the parking lot. We were in and out a lot during our stay so that was nice. Room was clean with your usual amenities nothing outstanding. Bathroom again fairly clean but the ..."

Reviewed on 1 Jul 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is £98 per night from 12 Jul to 13 Jul
£98
12 Jul - 13 Jul
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"This hotel was full for our 4 night stay, but the staff was on top of everything. Excellent housekeeping services, great location for purposes of our trip. Good food close by."

Reviewed on 2 Jul 2026

Crowne Plaza Annapolis by IHG
See all 1,190 properties in Chester
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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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
See properties

Frequently asked questions

How much does a Chester travel package cost?
Starting from a low £1,008, a package is your gateway to low-cost travel. Customize your Chester getaway by selecting from our extensive range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Chester travel package?
Yes, you can. We totally understand that things don't always go to plan, so we're here to help if you need to make changes to your Chester travel package. You may be able to change or cancel your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Chester?
Our Chester travel packages offer plenty of savings for the savvy traveller. For the best deal, simply combine your hotel, flights and extras (including tours) into a neat and tidy package. But cheap prices are just the beginning of your next memorable adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 properties across the globe to select from. Whatever your style, there's a package with your name on it.
Does Expedia offer Book Now, Pay Later Chester holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on your wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more cash to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that suits your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your trip over multiple transactions.
  • Low deposit holidays: Clicking on the "book now" button is easier with this option. Put down a small deposit on your escape and then get on your way.

Where should I stay in Chester?
If you hope to check out Chesapeake Exploration Centre, give commuting a miss and book a hotel close by. It's one of the top attractions in this area.
What are the top hotels in Chester?
Renaissance Baltimore Harborplace Hotel and Hyatt Regency Baltimore Inner Harbour are two of the most popular properties in Chester. Why not look up the rates and facilities at each and then make a decision?
How far in advance should I book my Chester holiday?
Your best bet is to book early. Air carriers usually release flight tickets up to 12 months ahead of departure, and this is a fantastic opportunity to land some rock-bottom prices. Just been told you should take your holiday time in a few weeks? That's alright! Expedia are never short on fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Chester travel package include?
Expedia has everything you need to arrange your Chester escape, but how you structure your package is entirely up to you. Select from a combination of rental cars, hotels and flights. Searching for some tours or experiences to keep you on the go? Once you've made your booking, you can add them too. No matter your budget or style, there's a package deal to match your needs.
What should I know before booking a Chester travel package?
Whether it's adventure or relaxation you're craving, a Chester travel package lets you organise your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Chester Expedia travel package?
Yes, you sure can. We have more than 550 partner airlines across the globe, so opt for the carrier that fits your budget and travelling style.

Explore a world of travel with Expedia

* 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.