Chester hotels

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Best Chester hotels

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Most recommended Chester hotels

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Holiday Inn Express & Suites Chester-Monroe-Goshen - Chester - Building
Holiday Inn Express & Suites Chester-Monroe-Goshen
Chester, NY
8.3Very good(775)
Parking
Free Wi-Fi
Pool
Spa
$167+
Check availability
Glenmere Mansion - Chester - Bedroom
Glenmere Mansion
Chester, NY
$427+
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Howard Johnson by Wyndham Newburgh/West Point - Newburgh - Building
Howard Johnson by Wyndham Newburgh/West Point
Newburgh, NY
6.0Okay(1106)
Parking
Free Wi-Fi
$104+
Check availability
Orange Inn Boutique Hotel - Goshen - Living room
Orange Inn Boutique Hotel
Goshen, NY
9.1Wonderful(29)
$269+
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Ramada by Wyndham Newburgh/West Point - Newburgh - Lobby
Ramada by Wyndham Newburgh/West Point
Newburgh, NY
3.6Poor(1024)
Parking
Free Wi-Fi
Pool
$106+
Check availability
Courtyard by Marriott Newburgh Stewart Airport - Newburgh - Lounge
Courtyard by Marriott Newburgh Stewart Airport
Newburgh, NY
8.0Very good(158)
Parking
Free Wi-Fi
Pool
$144+
Check availability
Newburgh Inn - Newburgh - Lobby
Newburgh Inn
Newburgh, NY
4.6Mediocre(394)
Parking
Free Wi-Fi
Pet friendly
$116+
Check availability
Hampton Inn & Suites Newburgh - Stewart Airport - Newburgh - Building
Hampton Inn & Suites Newburgh - Stewart Airport
Newburgh, NY
8.9Very good(441)
Parking
Airport shuttle
Free Wi-Fi
Pool
$150+
Check availability
Sleep Inn and Suites Monroe - Woodbury - Monroe - Patio
Sleep Inn and Suites Monroe - Woodbury
Monroe, NY
8.9Very good(818)
Free Wi-Fi
$120+
Check availability
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport - Newburgh - Building
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
Newburgh, NY
5.2Fair(1281)
Free Wi-Fi
Pet friendly
$87+
Check availability
Fairfield Inn & Suites by Marriott Goshen Middletown - Goshen - Bedroom
Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen, NY
8.7Very good(275)
Parking
Free Wi-Fi
Pool
$140+
Check availability
Homewood Suites by Hilton Newburgh-Stewart Airport - New Windsor - Living room
Homewood Suites by Hilton Newburgh-Stewart Airport
New Windsor, NY
8.6Very good(382)
Parking
Free Wi-Fi
Pool
Pet friendly
$155+
Check availability
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point - New Windsor - Building
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
New Windsor, NY
8.0Very good(1096)
Parking
Free Wi-Fi
Pool
Pet friendly
$116+
Check availability
Legoland New York Resort - Goshen - Bedroom
Legoland New York Resort
Goshen, NY
8.2Very good(143)
Free Wi-Fi
Pool
$340+
Check availability
Economy Inn - Newburgh
Economy Inn
Newburgh, NY
10Wonderful(1)
Free Wi-Fi
$265+
Check availability
Windsor Motel - New Windsor
Windsor Motel
New Windsor, NY
4.6Mediocre(151)
Free Wi-Fi
$95+
Check availability

Popular filters in Chester hotels

Hotels with parking
Holiday Inn Express & Suites Chester-Monroe-Goshen, Howard Johnson by Wyndham Newburgh/West Point and others
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$87 - $172$172 - $257$257 - $342$342 - $427$427+ per night

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KAYAK’s insights for hotels in Chester

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chester with confidence.

Which month has the cheapest hotel rates in Chester?

Hotels are cheapest in Chester in January, with average rates of $101. In comparison, February is the most expensive month, with prices at $453.

What is the cheapest day of the week to book a hotel in Chester?

Tuesday offers the lowest rates in Chester, with an average nightly price of $118. The highest prices are found on Monday, with average rates at $340.
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Good to know

Low season

January

High season

August

Average price (weeknight)

$145

Average price (weekend night)

$224
Cheapest month to stay with an average 40% drop in price.
Most expensive month to stay with an average 125% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chester hotel deals

  • If you’re looking for a cheap hotel in New York, you should consider visiting during the low season. You'll find cheaper hotels in New York in January and April.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in New York if you stay on a Thursday. The opposite is true for, Friday, which is usually the most expensive day.
  • How long should you stay? KAYAK users usually book their hotel in New York for 2 days.

FAQs when booking a hotel in Chester

Where to stay in Chester?

Our map will help you find the perfect place to stay in Chester by showing you the exact location of each hotel.

Everything you need to know for your stay in Chester

Chester Hotel Deals. Search and compare hotels in Chester. Find cheap hotel rooms in Chester. KAYAK searches hundreds of travel sites to help you find cheap hotels and book the room that suits you best.

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