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Top Chester hotels deals

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
Free cancellation
The price is CA $152 per night
CA $152
CA $187 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Castle Fun Center are located nearby.
Pool
Breakfast included
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $174 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Monteverde at Oldstone are located nearby.
Pool
Spa
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
1289 Route 300 Newburgh NY
Free cancellation
Reserve now, pay when you stay
The price is CA $91 per night
CA $91
CA $107 total
Oct 28 - Oct 29
includes taxes & fees
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Parking included
Free WiFi
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Free cancellation
The price is CA $174 per night
CA $174
CA $202 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lower Hudson Valley Challenger Learning Center and Spook Rock Golf Course are located nearby.
Pet-friendly
Free WiFi
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Free cancellation
The price is CA $144 per night
CA $144
CA $170 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orange County Community College and Paramount Theatre are located nearby.
Pool
Breakfast included
Inn on the Hudson

Inn on the Hudson

2 out of 5
634 Main Street Peekskill NY
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $169 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Peekskill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bear Mountain State Park and Peekskill Landing Park are located nearby.
Breakfast included
Pet-friendly
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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)
Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.
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Chester Vacations

Got your plane ticket in your hand and your luggage all packed? Read on for a few basic Chester tips before you set your foot out the door.

You'll discover this Newburgh neighborhood 16 miles (26 kilometers) southwest of the center of the city.

The population of Newburgh is roughly 29,000.

Hotels in Chester

Unpack your gear and hit the hay at one of the 3 properties just a quick commute from the middle of Chester. Unfortunately, places to stay are few and far between in the center, but a comfortable bed isn't all that far away!

Not sure where to lay your head? The Holiday Inn Express Hotel & Suites Chester (2 Bryle Place) and the Comfort Inn & Suites Goshen - Middletown (20 Hatfield Ln) are a hit with many visitors. Whether you opt for the first property or the second, you'll get a comfortable night's sleep.

Places to visit in Chester

Whether you're a pinball wizard or a compete newbie, Castle Fun Center has an awesome selection of arcade machines to suit all skill levels. And that's not all. Have you ever wondered how generations before us lived without the conveniences we have today? Stroll the time-worn streets of Museum Village and explore life as it was long ago.

Where do you fly into for Chester?

Stow your tray table, switch off the in-flight movie and get ready to touch down at LaGuardia Airport (LGA). Best part? You'll be only 45 miles (72 kilometers) to the southeast of Chester.

Frequently asked questions

How much are vacation packages to Chester?
Travelocity provides package deals to Chester, including hotels and flights, from an impressive . With the cash you save, you could purchase some cool tours or maybe also tack on some extra days to your exciting adventure.
How long should my Chester vacation be?
Around 2 nights is what many visitors book for their Chester trip. That's a handy guide, but there's loads more to explore if you allow yourself a couple of extra days.
Where can I get the best vacation package deals for Chester?
For an excellent package deal to Chester, book with Travelocity. Take your pick of 400 airlines and 1,000,000 properties across the globe to create your dream escape — it's really that easy.
Why should I book my Chester vacation package via Travelocity?
Whether you're planning a weeks-long vacation or a last-minute weekend escape, we have loads of amazing destinations to choose from at an affordable price. What's more, we provide 24/7 assistance, excellent service and a Price Match Guarantee. Save yourself the effort and time and secure your dream vacation now.
Can I save money on my Chester car rental if I bundle it with a hotel or flight?
With a Chester vacation package, you can combine your flight, hotel and car bookings and save tons. If you can't wait to uncover the best of this wonderful region, why not start with Times Square? This well-known attraction is 72 kilometers from Chester. With your own rental car, you'll be there in no time.
Which airport is best for Chester?
John F. Kennedy Intl. Airport (JFK) is popular. You'll find it around 88 kilometers southeast of Chester. Other options worth considering are Liberty Intl. Airport (EWR) (72 kilometers away from central Chester) and LaGuardia Airport (LGA) (72 kilometers away from central Chester).
What is there to do in Chester?
Chester is brimming with sights to explore, like The Rock Sports Complex and Museum Village. These well-known attractions are at the top of most travelers' itineraries.
Where should I stay when visiting Chester?
The Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is the number one choice of many visitors. Book now before it's too late.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.
A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".