Chester Holidays

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Chester Holiday

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
The price is NZ$255 per night from 30 Aug to 31 Aug
NZ$255
30 Aug - 31 Aug
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Booking a room their was easy. Receptionist was welcoming, professional and clear. Room was clean. Staff made sure breakfast was never empty."

Reviewed on 5 Aug 2026

Holiday Inn Express Hotel & Suites Chester by IHG
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Fully refundable
The price is NZ$241 per night from 30 Aug to 31 Aug
NZ$241
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (1,025 reviews)
"I travel frequently for both business and personal reasons, and I've experienced soundproofing issues in many hotels. However, the situation at this hotel was on a completely different level. I had to listen to the man in the next room repeatedly trying to clear his throat, as well as him scolding ..."

Reviewed on 5 Aug 2026

Crowne Plaza Suffern - Mahwah 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 NZ$247 per night from 11 Aug to 12 Aug
NZ$247
11 Aug - 12 Aug
includes taxes & fees
8.8/10 Excellent! (1,118 reviews)
"I enjoyed the spacious bathroom and the wall hanging shampoo and conditioner set up. The beds were super comfortable with clean white bedding. Ann who checked me in was very professional and helpful to direct me of the property. Breakfast in the common area completed my wonderful stay. Thank you, ..."

Reviewed on 5 Aug 2026

Sleep Inn & Suites Middletown - Goshen
See all 1,069 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.

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.