Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Chester flight + hotel deals
- JW Marriott Essex House New York
18 Jan - 23 JanJW Marriott Essex House New York + Flight
Manhattan5 nights4.5 star property8.8/10 - Excellent (1,001 reviews)Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct€2,116€1,425found 1 day agoper traveller - The St. Regis New York
18 Jan - 23 JanThe St. Regis New York + Flight
Manhattan5 nights5.0 star property9.2/10 - Wonderful (295 reviews)"The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"Reviewed November 6, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct€4,243€2,417found 1 day agoper traveller - Hotel Riu Plaza New York Times Square
26 Dec - 31 DecHotel Riu Plaza New York Times Square + Flight
Manhattan5 nights4.0 star property9.0/10 - Wonderful (3,454 reviews)"Three of us stayed in a room and paid extra for 3 people and a pull out coach. The coach did not open all the way. We got in late and dealt with it. We told the customer service department who we also sent pictures to. She had us register a complaint with corporate customer service. They basically said it was not true (see pictures below) and that we didn't say anything at the hotel, again, which is not true. The hotel is nice, great location and a nice breakfast, but disappointed in the..."Reviewed November 11, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct€4,005€2,635found 7 hours agoper traveller - The William Hotel Midtown, New York
26 Dec - 31 DecThe William Hotel Midtown, New York + Flight
Manhattan5 nights3.5 star property9.4/10 - Exceptional (304 reviews)Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct€2,982€1,981found 1 day agoper traveller - Margaritaville Resort Times Square
26 Dec - 30 DecMargaritaville Resort Times Square + Flight
Manhattan4 nights4.0 star property9.0/10 - Wonderful (4,182 reviews)"Very clean, staff was great and everything is nearby. No need for long rides, everything is close by. I will book again"Reviewed November 12, 2026Return • Dublin (DUB) - New York (JFK)DUB - EWR • Direct EWR - DUB • Direct€2,290€1,654found 21 hours agoper traveller
Discover the most popular places to visit in Chester
Chester Hotel Deals
"It was a lovely historic property. Our suite was large and comfortable. Having an excellent restaurant is also a plus."
"Showers were outdated, tub liner pealing some what"
"It was fine"
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Extended Stay America Suites Mt Olive Budd Lake
Extended Stay America Suites Mt Olive Budd Lake
Holiday Inn Budd Lake - Rockaway Area by IHG
Holiday Inn Budd Lake - Rockaway Area by IHG"I’m"
Holiday Inn Express Hotel & Stes Mt. Arlington Rockaway Area by IHG
Holiday Inn Express Hotel & Stes Mt. Arlington Rockaway Area by IHG"The desk clerk was very considerate and gave me a room handicap accessible. The equipment in the bathroom, tub, toilet,sink very clean. Checked the bed and bedding very comfortable, I slept like a baby. The breakfast was ok here, But will recommend to friends and the handicap community as well."
Residence Inn by Marriott Mt. Olive at Intl Trade Center
Residence Inn by Marriott Mt. Olive at Intl Trade Center"Overall clean, convenient, and friendly staff."
Frequently Asked Questions
How much does a Chester holiday package cost?
Offering excellent value package deals from €1,425 on Expedia, you'll be thrilled with how little a holiday to Chester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chester?
January, February and November are the best times to look for cheap Chester holiday packages. Opting to travel in less busy months means you can typically find reduced prices on flights and hotels.
How many days is enough for Chester?
With a well-planned schedule, you can easily hit the top Chester attractions in a handful of days. But if you want to venture off the beaten track or go on day tours, consider booking your Chester holiday for longer.
Is it worth booking a holiday package to Chester?
Popular for its hiking, markets and family-friendly attractions, a Chester holiday is a hit with all kinds of travellers. Be sure to check out leading sights like Alstede Farms and Hacklebarney Farm Cider Mill, and consider renting a set of wheels for day trips to discover even more.
How to find the best Chester package deals?
Landing a cheap Chester package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most economical Chester package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester escape by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Chester?
Land amazing discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chester escape.
How to plan a trip to Chester?
- Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Chester.
- Budget wisely: In addition to the price of your accommodation, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may come up during your trip to Chester.
- Decide your trip length: Consider how long you want to spend exploring Chester. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalised Chester holiday package.