Chester Holidays from £954

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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.
The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Price was £1,168, price is now £954 per person
£954
per person
12 Jan - 15 Jan
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9.8/10 Exceptional! (1,001 reviews)
Already spoke to manager about shower grab bars- young designers aren't aware of everyone's needs. Loved the TV in bathroom. There was no daily freshening up service??? Great food! VERY friendly! When we return to DC we will come back!

Reviewed on 24 Oct 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £1,921, price is now £1,323 per person
£1,323
per person
11 Dec - 18 Dec
found 1 day ago
Return flight included
London (LGW) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)
Great restaurant and fantastic location

Reviewed on 29 Oct 2026

The Potomac Hotel, Autograph Collection

The Potomac Hotel, Autograph Collection

5 out of 5
Southwest
Price was £1,865, price is now £1,438 per person
£1,438
per person
11 Dec - 18 Dec
found 1 day ago
Return flight included
London (LGW) to Baltimore (BWI)
9.4/10 Exceptional! (1,072 reviews)

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was £1,773, price is now £1,411 per person
£1,411
per person
11 Dec - 18 Dec
found 1 day ago
Return flight included
London (LGW) to Baltimore (BWI)
9.4/10 Exceptional! (1,629 reviews)

Hilton Club The District Washington D.C.

Hilton Club The District Washington D.C.

3.5 out of 5
Downtown Washington D.C.
Price was £1,549, price is now £1,269 per person
£1,269
per person
11 Dec - 18 Dec
found 1 day ago
Return flight included
London (LGW) to Baltimore (BWI)
9.4/10 Exceptional! (672 reviews)
Shared space with Embassy Suites. Lovely apartment type room and bedroom.

Reviewed on 30 Oct 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 £108 per night from 30 Nov to 1 Dec
£108
30 Nov - 1 Dec
includes taxes & fees
Historic Inns of 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 £86 per night from 10 Nov to 11 Nov
£86
10 Nov - 11 Nov
includes taxes & fees
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
The price is £73 per night from 29 Nov to 30 Nov
£73
29 Nov - 30 Nov
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"No airport shuttle, beware. Closing the hotel in November......."

Reviewed on 28 Oct 2026

Sonesta ES Suites Annapolis
See all 1,210 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
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Family Friendly Holidays

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

What to do in Chester

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

£119
per adult
100% of travellers recommend
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

£183
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

£202
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
See all activities in Chester

Frequently asked questions

How much does a Chester travel package cost?
Starting from a low £954, 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.