Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

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 3.632.209 ₫ per night from 14 Jul to 15 Jul
3.632.209 ₫
4.290.547 ₫ total
14 Jul - 15 Jul
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Helpful staff"

Reviewed on 20 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 2.900.541 ₫ per night from 6 Jul to 7 Jul
2.900.541 ₫
3.281.236 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Very nice, updated, clean and price was great. Pool and hot tub were also great."

Reviewed on 18 Jun 2025

HYATT house Fishkill/Poughkeepsie
Best Western The Inn At Ramsey
Best Western The Inn At Ramsey
3 out of 5
1315 Route 17 South, Ramsey, NJ
Fully refundableReserve now, pay when you stay
The price is 2.442.987 ₫ per night from 29 Jun to 30 Jun
2.442.987 ₫
2.800.275 ₫ total
29 Jun - 30 Jun
includes taxes & fees
7.2/10 Good! (1,002 reviews)
"N/A"

Reviewed on 14 Jun 2025

Best Western The Inn At Ramsey
See all 995 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.

Popular places to visit

Museum Village

You can spend an afternoon studying the exhibits at Museum Village in Chester. While in this family-friendly area, find time to visit its shops.

Museum Village

Goosepond Mountain State Park

You can take time to visit Goosepond Mountain State Park during your travels to Chester. Visit the shops in this family-friendly area or simply enjoy its restaurants.

Goosepond Mountain State Park