Chester Hotels

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Fast facts

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Highest rated hotelThe Inn at Stony Creek – 5
Cheapest month to bookMarch

Your guide to finding the best hotels in Chester, New York

Make the most of your time in Chester by booking a hotel that suits your style. Discover our favorite hotels that cater to every taste and budget, from luxurious to modest hotels.

Best time to visit Chester

The best time of year to visit Chester depends on what you’re looking for (or hoping to avoid) during your travels in terms of things like weather and price.

Low and high season in Chester

Busiest month(s): Chester experiences its peak season in July, leading to a higher average nightly rate. Those planning to travel during this period should be prepared for increased costs compared to the quieter times of year, when average nightly prices dip.

Quietest month(s): Save on hotel rooms and avoid peak season prices by taking your trip during July, when the average cost per night is $378.

July is the most expensive month to stay in Chester, so plan accordingly. When prices peak, you should be prepared to spend an average of $378 per night on a hotel stay. Prices are usually highest on Saturday. No matter the time of year, Monday is generally the cheapest day to make a reservation.

Where to stay in Chester, New York

With Skyscanner, it's easy to find the best Chester hotels at a rate you want. The best-rated hotels in Chester

If you want to experience the best of what the city has to offer, book a room in one of its top-rated hotels.

The Glenmere Mansion offers a great stay with its 5-star rating and range of services. The hotel offers an excellent retreat in the heart of Chester. You can enjoy the pool, restaurant, spa, and gym.

Popular hotels in Chester

With a pool, gym, restaurant and free Wi-Fi on site, the 2-star hotel Holiday Inn Express & Suites Chester-Monroe-Goshen, an IHG Hotel offers comfort and value.

Things to do in Chester

Visit well-known attractions and things to do like Long Lot Farm Brewery, The Castle Fun Center, and Sugar Loaf Performing Arts Center. If you love food, you'll find delicious local cuisine, creative spins on classics, and flavors from around the world at Glenmere Mansion, Allan's Falafel, Christopher's Bistro, Rustic Wheelhouse Restaurant, and The New Chester Diner.

Finding cheap hotels in Chester: FAQs

You can always cancel or amend your hotel reservation if you need to, but look out for hotels in Chester with free cancellation or flexible booking options if you want to protect your money. Some hotels allow you to cancel and get your money back if your plans change.
Of course - the cheapest hotel deal we found within the next seven days is $144 per night. If you need somewhere in the next 24 hours, we've found you somewhere to stay for $223 per night.
The average price of a hotel during the week is $187 per night, and the average price on weekends is $203. Overall, it looks like the cheapest day to stay in Chester could be Sunday.
We crunched some numbers on our calendar and found that Sunday is the cheapest day to stay in Chester. And the most expensive day seems to be Saturday
If you're hitting up Chester with kids in tow, try Fairfield Inn & Suites Goshen Middletown, or Home2 Suites by Hilton Middletown.