Chester Holidays from £507

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    Save up to £335 when you book a flight and hotel together*
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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
26 Sept - 1 Oct
found 1 day ago
Return direct flight included
London (LGW) to Washington (DCA)
8/10 Very Good! (968 reviews)
Staff was nice. Hotel is in deperate need of an upgrade

Reviewed on 10 Aug 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
26 Sept - 1 Oct
found 1 day ago
Return direct flight included
London (LGW) to Washington (DCA)
9.8/10 Exceptional! (28 reviews)
Beautiful lobby and bars, quiet and stellar staff!

Reviewed on 9 Aug 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
26 Sept - 1 Oct
found 1 day ago
Return direct flight included
London (LGW) to Washington (DCA)
9/10 Wonderful! (1,010 reviews)
Breakfast options were fantastic. Staff was friendly. Location was ideal for tourists.

Reviewed on 10 Aug 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
per person
26 Sept - 1 Oct
found 1 day ago
Return direct flight included
London (LGW) to Washington (DCA)
9.4/10 Exceptional! (1,012 reviews)
The property is beautifully designed and in a very nice area of DC - The Wharf has come a long way. I loved being on the water. The amenities were great. Pool is a bit small and was filled with kids but still enjoyed it. Very nice gym and on site bar and restaurant. The price is pretty high but not surprising being at the location its at. The parking is 65 a night so heads up. Dont know if id return but id recommend checking it out.

Reviewed on 10 Aug 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
per person
26 Sept - 1 Oct
found 1 day ago
Return direct flight included
London (LGW) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful facility inside Galludet University. Allowable price and free parking in the middle of Washington DC. Thoroughly enjoyed my stay. The room was large and had many amenities. My stay was quiet and peaceful. I will definitely be back!

Reviewed on 21 Jul 2025

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 Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester, MD
9.8/10 Exceptional! (91 reviews)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"

Reviewed on 27 Jul 2025

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Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
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
8.8/10 Excellent! (1,817 reviews)
"Liked the historic feel and the archeological dig site located just off the lobby (and still inside the hotel)! Tahina gave excellent customer support"

Reviewed on 8 Aug 2025

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Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is £132 per night from 17 Aug to 18 Aug
£132
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"This hotel is great. Good location accommodations are beautiful. The only thing they lack is a coffee maker in the room."

Reviewed on 7 Aug 2025

Graduate by Hilton Annapolis
See all 1,239 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chester travel package cost?
Starting from a low £507, 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.

* 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.