Chester Trip

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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 ₹12,115 per night from 26 Jul to 27 Jul
₹12,115
₹14,917 total
26 Jul - 27 Jul
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Big spacious room that actually fit all five of us and was super clean. The beds were so comfortable I slept like a baby. Microwave and fridge. The pool is very nice. Would highly recommend and will definitely be staying here again when we go out this way."

Reviewed on 3 Jul 2026

Holiday Inn Express Hotel & Suites Chester by IHG
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 ₹13,019 per night from 5 Jul to 6 Jul
₹13,019
₹16,029 total
5 Jul - 6 Jul
includes taxes & fees
8.4/10 Very good! (1,002 reviews)
"Fabulous stay on our way to Maine!"

Reviewed on 2 Jul 2026

Overlook Lodge at Bear Mountain
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is ₹9,566 per night from 12 Jul to 13 Jul
₹9,566
₹11,061 total
12 Jul - 13 Jul
includes taxes & fees
8.2/10 Very good! (152 reviews)
"Reasonable hotel for a short stay, we were flying from Newburgh airport which is only 15 mins away. The communal areas are in need of a refurb and had a bleach smell but the room was fairly modern and clean. Breakfast is very basic. Good number of restaurants within a 5 minute walk. Overall, I would ..."

Reviewed on 3 Jul 2026

Spark by Hilton Fishkill
See all 1,073 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.
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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.