Chester Holidays

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Your Chester Holiday

Take the stress out of planning your next amazing adventure with a Chester holiday package. Whether you're lured here by its food, entertainment or something else, there's an inexhaustible array of experiences to be had. LEGOLAND® New York, The Rock Sports Complex and Castle Fun Centre are just some of the many attractions worth checking out during your trip to Chester. Expedia is here to help you escape your daily routine. Tailor your holiday to Chester to suit your style of travel, whatever that may be.

Chester Holiday

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
3,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Brotherhood Winery, Warwick Valley Winery and Distillery and Mount Peter Ski Area

Our pick of the best Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Fully refundable
The price is AU$174 per night from 26 July to 27 July
AU$174
26 July - 27 July
includes taxes & fees
8.6/10 Excellent! (1,025 reviews)
"Stayed at this hotel because the reviews were promising. When I arrived, the building was a little run down and the man behind the counter was nice and inviting, however I had to ask for my room to be switched 4 times as the family above me room had their kids just running around and banging making ..."

Reviewed on 9 July 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is AU$202 per night from 26 July to 27 July
AU$202
26 July - 27 July
includes taxes & fees
8.8/10 Excellent! (1,076 reviews)
"The property is very clean and well maintained. The area around the hotel is ok. It is easy to access from the highway. The beds are on the hard side, they aren't the worst I've slept in but they did make my back hurt."

Reviewed on 10 July 2026

Sleep Inn & Suites Middletown - Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is AU$248 per night from 2 Aug to 3 Aug
AU$248
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"Friendly atmosphere and staff. Lots to see and do! A bit outdated so must be ok with a outdoorsy/rustic feel."

Reviewed on 8 July 2026

Overlook Lodge at Bear Mountain
See all 1,058 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
All Inclusive Holidays
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Beach Holidays
Beach Holidays

Stay near popular Chester attractions

The Rock Sports Complex

8.0/10 (18 reviews)
This dedicated sports venue hosts baseball and softball tournaments on well-maintained turf fields. Bring portable chairs and sun protection to enjoy the games in comfort at this local athletic hub.
See properties

Frequently asked questions

How much does a Chester holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
You can typically find lower prices and better availability in January, February and March. Browse our cheap Chester holiday packages and you could land some excellent off-season deals.
How many days is enough for Chester?
We recommend booking a Chester holiday for at least 2 days. This will allow you plenty of time to check off top sights such as Castle Fun Centre and The Rock Sports Complex, as well as explore neighbourhoods like South Blooming Grove and Walton Park. You might even be able to slot in a day trip outside of Chester.
Is it worth booking a holiday package to Chester?
Chester is a good holiday destination with attractions like The Rock Sports Complex among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Chester holiday promises a good time for everyone.
How to find the best Chester package deals?
Finding a cheap Chester package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Chester package deals. Want a simple trick to score even more savings? Be flexible 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?
An Expedia holiday package could land you great savings when compared to booking flights and accommodation separately. Better still, you can personalise your Chester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Chester?
If you have your Chester travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Chester?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the activities available will also help you decide when to holiday in Chester.
  2. Plan your budget wisely: Besides the cost of your accommodation, you should factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chester.
  3. Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Chester. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chester holiday package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.