Chester Holidays

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Top hotels in Chester

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 S$189 per night from 22 Jun to 23 Jun
S$189
22 Jun - 23 Jun
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Carpet in hallway needed vacuuming, carpet in my room (200) may have been vacuumed but needes shampooing or spot cleaning. But check in staff was great,Dev. I think was his name."

Reviewed on 5 Jun, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is S$161 per night from 6 Jul to 7 Jul
S$161
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"I really liked the location. So close to highway exit, easy to park. Close to shops and resturants and they even have a bar with snack (finger food)."

Reviewed on 12 Jun, 2025

HYATT house Fishkill/Poughkeepsie
Extended Stay America Suites Ramsey Upper Saddle River
Extended Stay America Suites Ramsey Upper Saddle River
2.5 out of 5
112 State Hwy. 17, Ramsey, NJ
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 17 Jun to 18 Jun
S$149
17 Jun - 18 Jun
includes taxes & fees
6.6/10 (974 reviews)
"This extended stay in New Jersey had construction on either side, so there was a lot of construction noise and I think most of the clients are people coming in for work to New Jersey or in and out of there we were there as a pitstop on the way to some somewhere else. It is a very basic room there’s ..."

Reviewed on 14 Jun, 2025

Extended Stay America Suites Ramsey Upper Saddle River
See all 993 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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.