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
2 Bryle Place Chester NY
Fully refundable
£96
30 Aug - 31 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The elevator was broke. Room was on top floor had to carry luggage and personals up 3 flights of stairs. Room floor was slanted. Just not a good stay."
Reviewed on 24 Aug 2026
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd Suffern NY
£108
30 Aug - 31 Aug
includes taxes & fees
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
£95
21 Sept - 22 Sept
includes taxes & fees
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.
Museum Village
9.0/10 (8 reviews)
Step back in time at Museum Village, where costumed interpreters bring 19th-century rural American life to vivid reality. Explore historic buildings and watch traditional craftspeople demonstrate forgotten skills.
Goosepond Mountain State Park
8.0/10 (5 reviews)
This 1,558-acre undeveloped park offers a tranquil escape with diverse trails through woods, fields, and wetlands. Bring binoculars to spot songbirds from the boardwalk that crosses marshy areas.
Sugar Loaf Performing Arts Center
You can make plans for a show at Sugar Loaf Performing Arts Center during your trip to Sugar Loaf. Make some time to visit the shops while you're in the area.
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.
* 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.
