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Hotels in Chester

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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
  • 8 min walk from Castle Fun Center
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 ...
8.6/10 Excellent! (1,001 reviews)
"Excellent breakfast. Very clean rooms. Bathrooms/shower needs to be updated."

Reviewed on Jun 30, 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
  • 44 min drive from Castle Fun Center
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 ...
8.4/10 Very Good! (1,009 reviews)
"Eh… understaffed, depressing. loud rooms (stone cottages) - could hear other rooms’ conversations and snoring and doors SLAMMING… as well as LOUD vehicles on adjacent road continuously.. we are learning where to stay for our kid at West Point …. This was trial 1 at a local “hotel”"

Reviewed on Jun 30, 2026

Overlook Lodge at Bear Mountain
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
  • 1 hour drive from Castle Fun Center
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (148 reviews)
"No cups in the room. Ants in the breakfast area."

Reviewed on Jun 30, 2026

Spark by Hilton Fishkill
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
  • 23 min drive from Castle Fun Center
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 ...
8.8/10 Excellent! (1,046 reviews)
"Rooms were clean. Pool was great. Breakfast was nice variety. Only thing there was bridal or wedding party going on all night across the hall way. People were very loud and disrespectful. Even staff had to warn them several times. That was only frustrating part, I couldn’t truly enjoy my stay with ..."

Reviewed on Jul 1, 2026

Sleep Inn & Suites Middletown - Goshen
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
  • 1 hour drive from Castle Fun Center
Book a stay at this golf hotel in Nanuet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,160 reviews)
"Parfait"

Reviewed on Jun 28, 2026

DoubleTree by Hilton Hotel Nanuet
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
  • 48 min drive from Castle Fun Center
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,005 reviews)
"The hotel was updated and clean and perfect to accompany a small dog. They can have more electric chargers."

Reviewed on Jun 30, 2026

Crowne Plaza Suffern - Mahwah by IHG
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
  • 21 min drive from Castle Fun Center
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (1,007 reviews)
"My family and I had a wonderful stay here! It was conveniently located close to LEGOLAND, which made our trip so much easier. The boys absolutely loved the pool, and the complimentary breakfast was surprisingly phenomenal with plenty of great options. The gym was perfect for me to do a bit of strength ..."

Reviewed on Jun 30, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Days Inn by Wyndham Nanuet / Spring Valley

Days Inn by Wyndham Nanuet / Spring Valley

2 out of 5
367 W Route 59 Nanuet NY
  • 59 min drive from Castle Fun Center
Book a stay at this business-friendly motel in Nanuet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
7/10 Good! (1,004 reviews)
"Friendly staff. Clean room."

Reviewed on Jun 28, 2026

Days Inn by Wyndham Nanuet / Spring Valley
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
1289 Route 300 Newburgh NY
  • 39 min drive from Castle Fun Center
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 ...
4.8/10 (1,002 reviews)
"This is a bait and switch.the rooms posted are for"

Reviewed on Jul 1, 2026

Ramada by Wyndham Newburgh/West Point
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
  • 36 min drive from Castle Fun Center
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,006 reviews)
"No coffee pot in room. No clock in room. Only one suitcase stand for two people"

Reviewed on Jun 29, 2026

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Inn on the Hudson

Inn on the Hudson

2 out of 5
634 Main Street Peekskill NY
  • 54 min drive from Castle Fun Center
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 ...
7.2/10 Good! (1,000 reviews)
"Like: convenient to train station and walking distance to downtown for dining, nice view of the river. Good shower water pressure and temperature. Dislike: property is old and needs updating. Rooms need renovation, including new mattresses and bedding, room darkening window shades/treatments. Closet ..."

Reviewed on Jun 30, 2026

Inn on the Hudson
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
1 Sleep Way Monroe NY
  • 14 min drive from Castle Fun Center
Book a stay at this business-friendly hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,094 reviews)
"Room was clean, Staff was friendly."

Reviewed on Jun 30, 2026

Sleep Inn & Suites Monroe - Woodbury
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.

Find cheap hotels in Chester

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How many hotels are there in Chester?

With over 1,082 hotels in Chester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $85.

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Finding a cheap car rental deal in Chester is as easy as scoring cheap hotels in Chester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.