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
The price is €136 per night from 8 Apr to 9 Apr
€136
includes taxes & fees
8 Apr - 9 Apr
8.4/10 Very Good! (1,001 reviews)
"It was nice, clean. My only disappointment was that the pool was closed for maintenance. Had i known, I would"

Reviewed on 30 Mar 2025

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 State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is €152 per night from 10 Apr to 11 Apr
€152
includes taxes & fees
10 Apr - 11 Apr
8/10 Very Good! (1,004 reviews)
"Very nice seasonal outdoor hotel. Great views. Not too much activities outside od seasonal time, but still have wonderful views"

Reviewed on 3 Apr 2025

Overlook Lodge at Bear Mountain
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is €129 per night from 20 Apr to 21 Apr
€129
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (1,002 reviews)
"Easy on off access to 84"

Reviewed on 31 Mar 2025

Sleep Inn & Suites Middletown - Goshen
See all 984 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.