Chester Holidays

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Your Chester Holiday

The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester holiday package that's customised to you. If taking in sights is on the agenda during your trip to Chester, swing by leading attractions like LEGOLAND® New York, The Rock Sports Complex and Goshen Historic Track. Don't delay visiting this destination any longer. Your ultimate Chester holiday is a couple of clicks away with Expedia.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
3,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Brotherhood Winery, Warwick Valley Winery and Distillery and Mount Peter Ski Area

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 £90 per night from 26 Jul to 27 Jul
£90
26 Jul - 27 Jul
includes taxes & fees
8.6/10 Excellent! (1,021 reviews)
"The Family got in the car n took a road trip they were they accommodated us for a short last minute reservation the price was reasonable the room had enough space for us it was clean the pool was open we enjoyed our night there we will do it again in"

Reviewed on 8 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 £132 per night from 21 Jul to 22 Jul
£132
21 Jul - 22 Jul
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"Friendly atmosphere and staff. Lots to see and do! A bit outdated so must be ok with a outdoorsy/rustic feel."

Reviewed on 8 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 £87 per night from 9 Aug to 10 Aug
£87
9 Aug - 10 Aug
includes taxes & fees
8.4/10 Very good! (159 reviews)
"Room is clean, which is important to me. Staff is friendly, breakfast, ok."

Reviewed on 6 Jul 2026

Spark by Hilton Fishkill
See all 1,059 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.
All Inclusive Holidays
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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 travel package cost?
Discover the best of Chester from just . We offer a great selection of rental cars, hotels and flights to suit every budget. You can score even better deals when you add some tours or activities to your travel package.
If I'm not able to travel, can I cancel my Chester travel package?
It's impossible to predict what tomorrow might bring, so it's good to know that you can cancel or change your Chester travel package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.
How do I get a cheap travel package to Chester?
If you love amazing deals, bundle your bookings into a Chester travel package. Whether you're looking for hotels, flights, tours or rental cars, you can browse and book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotels throughout the world to choose from. Fly with who you want, stay wherever you like and save a bundle — now that's the ideal escape!
Does Expedia offer Book Now, Pay Later Chester holidays?
We do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that suits best during the checkout process and take away the stress of budgeting for your next trip. Remember to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your holiday buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all types of budgets, so you can have that well-deserved holiday sooner.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Hitting the "book now" button is easier with this option. Just put down a small deposit on your holiday and then start packing your suitcase.

Where should I stay in Chester?
With fascinating attractions like LEGOLAND® New York and Castle Fun Centre in this neighbourhood, try to find a hotel near them. Museum Village is another sight in Chester that draws the crowds.
What are the top hotels in Chester?
Get your trip off to an excellent start by locking in a room at Super 8 by Wyndham Newburgh/West Point Near Stewart Airport. It's one of most popular hotels in Chester. Another option is Hampton Inn Harriman Woodbury.
How far in advance should I book my Chester holiday?
Savvy travellers book early. Airlines usually advertise flights around a year ahead of departure, and this is a fantastic opportunity to score some rock-bottom prices. Boss just told you to use up all your holiday days next week? That's fine too — Expedia are never short of fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Chester travel package include?
Flights, rental cars and hotels, or any combination of the three — the choice is all yours! Whether you're exploring Chester on a family road trip or travelling with your friends, there's a package to suit your style and budget. Once you've made your booking, why not add on one or two tours or activities?
What should I know before booking a Chester travel package?
When you book your flights, hotels and car rentals together, you'll pick up incredible discounts. Whether you're planning an island getaway in a villa or prefer to stay in a luxurious city hotel, Expedia will make it happen for less.
Can I choose my airline with a Chester Expedia travel package?
With a travel package, you're the boss. Whether you're hoping to fly to Chester in business or coach, simply pick from the available airline options. Expedia has access to more than 550 airline partners across the world.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.