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Tonight
Check prices in Chester for tonight, Oct 3 - Oct 4
Oct 3 - Oct 4
Tomorrow night
Check prices in Chester for tomorrow night, Oct 4 - Oct 5
Oct 4 - Oct 5
Next weekend
Check prices in Chester for next weekend, Oct 9 - Oct 11
Oct 9 - Oct 11

Most frequently booked Chester hotels

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
1.33 km from city centre
The price is CA $186 per night
CA $186
CA $229 total
Oct 19 - Oct 20
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
23.83 km from city centre
The price is CA $124 per night
CA $124
CA $153 total
Nov 3 - Nov 4
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
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Free cancellation
30.11 km from city centre
The price is CA $174 per night
CA $174
CA $202 total
Oct 6 - Oct 7
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
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
Free cancellation
Reserve now, pay when you stay
14.21 km from city centre
The price is CA $171 per night
CA $171
CA $202 total
Nov 2 - Nov 3
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 helpful staff and the clean rooms in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
Pool
Breakfast included
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Free cancellation
34.52 km from city centre
The price is CA $139 per night
CA $139
CA $161 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Blodgett Memorial Library and Fishkill Ridge are located nearby.
Pool
Breakfast included
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Free cancellation
14.63 km from city centre
The price is CA $154 per night
CA $154
CA $182 total
Nov 1 - Nov 2
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
29.73 km from city centre
The price is CA $148 per night
CA $148
CA $170 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
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
Free cancellation
Reserve now, pay when you stay
21.71 km from city centre
The price is CA $127 per night
CA $127
CA $150 total
Oct 18 - Oct 19
includes taxes & fees
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 clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and New Windsor Cantonment State Historic Site are located nearby.
Pool
Pet-friendly
Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

3 out of 5
270 W Route 59 Nanuet NY
Free cancellation
Reserve now, pay when you stay
35.8 km from city centre
The price is CA $175 per night
CA $175
CA $204 total
Oct 11 - Oct 12
includes taxes & fees
Book a stay at this business-friendly hotel in Nanuet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Shops at Nanuet and Regal Nanuet are located nearby.
Hot tub
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.

Top family friendly Chester hotel deals

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY
The price is CA $186 per night from Oct 19 to Oct 20
CA $186
CA $229 total
Oct 19 - Oct 20
includes taxes & fees

Top hotels in Chester for Extended Stay

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY

Greenwood Lake NY
The price is CA $314 per night from Nov 1 to Nov 2
CA $314
CA $400 total
Nov 1 - Nov 2
includes taxes & fees
10/10 Exceptional! (13 reviews)
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.

Chester hotels essential information

Accommodation
1,079 hotels
Lowest Price
CA $150
Highest Price
CA $400
Popular hotels
Holiday Inn Express Hotel & Suites Chester by IHG, Overlook Lodge at Bear Mountain, Crowne Plaza Suffern - Mahwah by IHG, La Quinta Inn & Suites by Wyndham Middletown-Goshen, Comfort Suites Fishkill near Interstate 84, Sleep Inn & Suites Middletown - Goshen, Inn on the Hudson, Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point, Hilton Garden Inn Nanuet

Frequently asked questions

What are the top kid-friendly hotels in Chester?
Family vacations are where the best memories are made, but it's no secret that traveling with little ones can be challenging. These kid-friendly Chester hotels offer perks designed to keep guests of all ages comfortable and happy: Your entourage will love staying at 6 bedroom colonial house. A playground and free WiFi are a few of the things that help make this property a favorite. Alternatively, spend your Chester break at Holiday Inn Express Hotel & Suites Chester, an IHG Hotel. Take advantage of a swimming pool, complimentary breakfast and more here.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is CA $150 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 1,079 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during January, February and March. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

4 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Good hotel for the price, breakfast very good"
A verified traveller stayed at Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen