Chester Holidays from £960

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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!

The Latest Chester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
Clean and convenient

Reviewed on 24 Jun 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
3 Sept - 9 Sept
found 18 hours ago
Return flight included
Glasgow (GLA) to Washington (DCA)
No reviews
My husband and I stayed here for our anniversary and it did not disappoint. We will definitely be coming back. The staff, the hotel, the restaurants- all absolutely amazing.

Reviewed on 22 Jun 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
1 Aug - 8 Aug
found 11 hours ago
Return direct flight included
London (LHR) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
The property was beautiful and centrally located to attractions.

Reviewed on 24 Jun 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.2/10 Wonderful! (598 reviews)
It’s a nice looking hotel & they have friendly, helpful staff. Location is convenient & near the metro. BUT the rooftop bar parties are loud & occupy ALL the elevators all evening. Even on Sunday night. It’s also hot in lobby where you wait in line on the elevators as drunk party goers are stuffed into the elevators like sardines on their way down from the roof. Perhaps Arlo should just designate one or two elevators specifically for the roof bar!! Can hear roof bar dj music 3 blocks away - so easy to locate the Arlo coming back in the dark from metro, lol. Never got to use the pool in evening as next to the loud packed bar - pool is small. They charge a fee for amenities & you don’t really get to use. In our two queens room it was actually fairly quiet & comfy but very crowded in all the public spaces over the 3 nights we stayed. Mini fridge was convenient - tho hard to find any ice. I’d stay again if i knew for sure it was not a rooftop dj night. Shower worked great & bed was comfy.

Reviewed on 25 Jun 2025

Hilton Garden Inn Washington DC Downtown

Hilton Garden Inn Washington DC Downtown

3 out of 5
Downtown Washington D.C.
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
8.6/10 Excellent! (1,006 reviews)
The hotel location is great for my business trips.

Reviewed on 24 Jun 2025

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
1 Aug - 8 Aug
found 11 hours ago
Return direct flight included
London (LHR) to Washington (DCA)
8.8/10 Excellent! (2,464 reviews)
Clean, excellent quality, friendly stuff. Restaurant is of an excellent quality, although maybe a little more expensive that I would expect. Good location for the purpose of my visit. Relatively far from the subway stations though; however buses are coming near.

Reviewed on 19 Jun 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

Our pick of the best Chester Hotel Deals

Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,792 reviews)
"Close to shops, restaurants , water front, and nightlife"

Reviewed on 23 Jun 2025

Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful ...
8.4/10 Very Good! (1,001 reviews)
"It was very nice and comfortable"

Reviewed on 22 Jun 2025

Hilton Garden Inn Annapolis Downtown
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3 out of 5
2600 Housley Road, Annapolis, MD
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,006 reviews)
"Great accommodations"

Reviewed on 20 Jun 2025

Country Inn & Suites by Radisson, Annapolis, MD
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 £960, 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.