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Chester New York Accommodations

Find accommodations in Chester with the hotel list provided below. Find discounted hotel accommodations in or close to Chester, NY for your upcoming individual or group travel. Discover the most favored Chester New York hotel/motel rooms. Review the Chester hotel list below to find the perfect lodging. We also have a map of the Chester hotels. Planning a group? Lock in Chester Group Hotel Discounts

The Chester center point is around 2 miles northeast of The Rock Sports Park/Frozen Ropes and 7 miles southwest of Brotherhood Winery.

Located in the state of New York, Chester is a captivating destination that effortlessly combines the charm of small-town America with a dash of cosmopolitan allure. Steeped in history and culture, it is a colorful tapestry of scenic natural beauty, historic landmarks, and unique attractions that beckon visitors from far and wide. From the captivating Heritage Trail offering breathtaking views and leisurely strolls to the fascinating 1915 Erie Station, which takes you back in time, Chester is an unexplored gem teeming with exciting sights. The town also hosts a variety of events throughout the year, including the Chester Fall Festival, providing a glimpse into the area's rich culture and artisanal heritage. Foodies will delight in Chester's culinary scene, which ranges from lovely cafes to gourmet restaurants, where local produce takes center stage. Moreover, the town is well-equipped to welcome visitors, boasting a range of lodgings to suit all budgets and preferences. From cozy motels and inns to modern hotels and suites with all the conveniences, you'll find plenty of options available in and around the area. These accommodations provide not only comfortable and well-appointed rooms but also excellent amenities such as free Wi-Fi, complimentary breakfast, fitness centers, and more. This makes the destination not just an intriguing place to visit but a convenient one as well. More from this guide...

Chester Hotels/Accommodations

Holiday Inn Express & Suites
+1-888-389-4121
2 Bryle Pl, Chester, NY 10918
  • 3 star Rural property
  • Check in time: 3:00pm
From$109
Very Good 4.0 /5 Read Reviews Call BookMore Details
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Sleep Inn & Suites Monroe - Woodbury : 1 Sleep Way
+1-888-675-2083
1 Sleep Way, Monroe, NY 10950 ~3.82 miles east of Chester
  • Three Star Suburban hotel
  • Fitness + Health Center
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Goshen Middletown in Goshen
+1-800-716-8490
20 Hatfield Lane, Goshen, NY 10924 ~4.70 miles northwest of Chester
  • Affordable Suburban property
  • 3 conference rooms in property
From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Arrow Park
+1-800-805-5223
1061 Orange Turnpike, Monroe, NY 10950 ~6.41 miles southeast of Chester
  • Economical Lake property
  • 4 suites in hotel
From$375
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn Harriman Woodbury
+1-888-965-1860
60 Centre Dr., Central Valley, NY 10917 ~7.62 miles east of Chester
  • 3-star Mountain hotel
  • Free complimentary breakfast
From$80
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Americas Best Value Inn Central Valley in Central Valley
+1-888-788-5576
139 Route 32, Central Valley, NY 10917 ~7.64 miles east of Chester
  • 2-star Suburban hotel
  • 45 rooms in property
From$68
Average 3.0 /5 Guest Reviews Call BookMore Details
Microtel Inn & Suites by Wyndham Middletown
+1-888-897-9207
19 Crystal Run Crossing, Middletown, NY 10941 ~8.14 miles northwest of Chester
  • 2-star Highway property
  • 3 floors in hotel
From$72
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Courtyard by Marriott
+1-888-311-4278
24 Crystal Run Crossing, Middletown, NY 10941 ~8.15 miles northwest of Chester
  • Three Star Suburban property
  • 4 suites in hotel
From$105
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Hampton Inn Middletown Ny
+1-888-469-4795
20 Crystal Run Crossing, Middletown, NY 10941 Website ~8.19 miles northwest of Chester
  • Low Cost Suburban hotel
  • Hotel has 6 suites
From$60
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen in Middletown
+1-888-734-9421
20 Med Parc Rd., Middletown, NY 10940 ~8.39 miles northwest of Chester
  • Mid-scale Downtown hotel
  • 93 sleeping rooms in hotel
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Days Inn by Wyndham Middletown
+1-888-841-5292
4939 Route 17 M, New Hampton, NY 10958 ~8.44 miles west of Chester
  • Cheap Suburban property
  • Check in time: 1pm
TRU by Hilton Middletown
+1-888-455-5160
41 Dunning Rd., Middletown, NY 10940 ~8.76 miles northwest of Chester
  • 2 star hotel
  • Hotel has 104 rooms
From$104
Average 3.0 /5 Read Reviews Call BookMore Details
Home2 Suites by Hilton Middletown
+1-888-965-8297
600 Route 211 East, Middletown, NY 10941 ~9.18 miles northwest of Chester
  • Affordable Suburban property
  • 95 sleeping rooms in hotel
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Super 8 by Wyndham Middletown
+1-888-906-6358
563 Route 211 East, Middletown, NY 10940 ~9.34 miles northwest of Chester
  • 2-star Highway property
  • Check in time: 3:00pm
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Middletown in Middletown
+1-888-749-6785
551 Route 211 East, Middletown, NY 10941 ~9.36 miles northwest of Chester
  • 2-star Suburban property
  • Check in time: 4:00 PM
From$48
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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Residence Inn Middletown Goshen - Middletown
+1-888-878-9982
57 Tower Dr., Middletown, NY 10941 ~9.45 miles northwest of Chester
  • Midscale Suburban hotel
  • Hotel has 125 suites
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Sleep Inn & Suites Middletown Goshen
+1-888-389-4485
3491 Route 6, Middletown, NY 10940 ~9.61 miles west of Chester
  • Inexpensive Highway hotel
  • Free breakfast available
From$89
Very Good 4.5 /5 Read Reviews Call BookMore Details
Super 8 by Wyndham Montgomery Maybrook : 207 Montgomery Rd.
+1-888-389-4121
207 Montgomery Rd., Montgomery, NY 12549 ~10.78 miles north of Chester
  • Low-priced Airport property
  • Check-in: 3:00pm
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery, an IHG Hotel
+1-888-675-2083
2105 Ny 208, Montgomery, NY 12549 ~11.42 miles north of Chester
  • Three Star property
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery, an IHG Hotel - Montgomery
+1-800-716-8490
2105 State Route 208, Montgomery, NY 12549 ~11.43 miles north of Chester
  • 3-star Highway property
  • Free breakfast available
From$96
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites Stewart Airport in New Windsor
+1-800-805-5223
180 Breunig Rd., New Windsor, NY 12553 ~12.67 miles northeast of Chester
  • High end Rural property
  • 125 rooms in hotel
From$79
Average 3.0 /5 Read Reviews Call BookMore Details
Econo Lodge Near Stewart Inter
+1-888-965-1860
310 Windsor Highway, New Windsor, NY 12553 ~13.42 miles northeast of Chester
  • Inexpensive Rural hotel
  • Hotel has 7 suites
From$60
Poor 2.0 /5 Reviews Call BookMore Details
Econo Lodge Near Stewart Inter in New Windsor
+1-888-788-5576
310 Windsor Highway Sr 32, New Windsor, NY 12550 ~13.44 miles northeast of Chester
  • Cheap hotel
  • Hotel has 38 rooms
From$60
Poor 2.0 /5 Reviews Call BookMore Details
Red Roof Inn & Suites Newburgh – Stewart Airport - New Windsor
+1-888-897-9207
915 Union Ave. I 84, New Windsor, NY 12553 ~13.61 miles northeast of Chester
  • Economy Airport property
  • 97 rooms in hotel
From$100
Very Good 4.0 /5 Read Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport : 4 Governor Dr.
+1-888-311-4278
4 Governor Dr., Newburgh, NY 12550 ~13.85 miles northeast of Chester
  • 3 star Rural hotel
  • Fitness + Health Center
From$114
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Crossroads Hotel - Newburgh, Ascend Hotel Collection in Newburgh
+1-888-469-4795
5 Lakeside Rd., Newburgh, NY 12550 ~14.07 miles northeast of Chester
  • 3-star Airport property
  • Gym / Fitness Center Available
From$109
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport
+1-888-734-9421
1 Crossroads Court, Newburgh, NY 12550 ~14.20 miles northeast of Chester
  • 3 star Suburban property
  • Check in time: 3:00pm
From$139
Very Good 4.0 /5 Review Score Call BookMore Details
Hudson Valley Hotel and Conference Center by Fairbridge
+1-888-841-5292
90 Rt. 17k, Newburgh, NY 12550 ~14.35 miles northeast of Chester
  • Economy Highway property
  • Check in time: 3pm
Howard Johnson by Wyndham Newburgh / West Point : 95 State Route 17k
+1-888-455-5160
95 State Route 17k, Newburgh, NY 12550 ~14.38 miles northeast of Chester
  • Two star Highway property
  • 74 rooms in hotel
Bear Mountain Inn : 3020 Seven Lakes Dr.
+1-888-965-8297
3020 Seven Lakes Dr., Bear Mountain, NY 10911 ~14.46 miles east of Chester
  • Affordable Mountain hotel
  • Check-in time: 3:00pm
From$149
Very Good 4.0 /5 Reviews Call BookMore Details
Ramada by Wyndham Newburgh/West Point
+1-888-906-6358
1289 Route 300, Newburgh, NY 12550 ~14.57 miles northeast of Chester
  • Cheap Airport property
  • 2 floors in hotel
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport - Newburgh
+1-888-749-6785
1287 Route 300, Newburgh, NY 12550 ~14.57 miles northeast of Chester
  • Low Cost Airport hotel
  • Comp. Breakfast
Windsor Motel
+1-888-878-9982
2976 Us Route 9w, New Windsor, NY 12553 ~14.90 miles northeast of Chester
  • Cheap property
  • Check-in time: 2:00 P.M
Holiday Inn Express West Point, an IHG Hotel in Fort Montgomery
+1-888-389-4485
1106 Rt. 9w, Fort Montgomery, NY 10922 ~14.98 miles east of Chester
  • Mid-scale hotel
  • Check in: 3:00 PM
From$170
Very Good 4.0 /5 Guest Reviews Call BookMore Details
FairBridge Inn & Suites at West Point
+1-888-389-4121
17 Main St., Highland Falls, NY 10928 ~15.20 miles east of Chester
  • Two star Suburban hotel
  • 2 floors in hotel
From$52
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Thayer Hotel : 674 Thayer Rd.
+1-888-675-2083
674 Thayer Rd., West Point, NY 10996 ~16.18 miles east of Chester
  • 3-star Suburban hotel
  • 151 rooms in property
From$108
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill : 2 John Walsh Blvd.
+1-800-716-8490
2 John Walsh Blvd., Peekskill, NY 10566 ~17.78 miles east of Chester
  • 3 star Riverfront hotel
  • Comp. Breakfast
From$97
Average 3.0 /5 Recent Reviews Call BookMore Details
Inn on the Hudson in Peekskill
+1-800-805-5223
634 Main St., Peekskill, NY 10566 ~18.05 miles east of Chester
  • 2-star Riverfront property
  • Hotel has an eco-friendly policy See policy
From$109
Average 3.0 /5 Read Reviews Call BookMore Details
The Abbey Inn & Spa : 900 Fort Hill Rd.
+1-888-965-1860
900 Fort Hill Rd., Peekskill, NY 10566 ~18.06 miles east of Chester
  • Four-star Riverfront hotel
  • 6 suites in hotel
From$500
Average 3.0 /5 Recent Reviews Call BookMore Details
Crowne Plaza Suffern - Mahwah, an IHG Hotel : 3 Executive Blvd.
+1-888-788-5576
3 Executive Blvd., Suffern, NY 10901 ~18.12 miles southeast of Chester
  • 3-star Suburban property
  • Gym is available on property
From$149
Very Good 4.0 /5 Review Score Call BookMore Details
Sheraton Mahwah
+1-888-897-9207
1 International Blvd., Mahwah, NJ 07495 ~18.13 miles south of Chester
  • High end Suburban property
  • 22 floors in hotel
From$129
Average 3.5 /5 Latest Reviews Call BookMore Details
Howard Johnson by Wyndham Suffern in Suffern
+1-888-311-4278
17 North Airmont Rd., Suffern, NY 10901 ~18.39 miles southeast of Chester
  • 2-star Highway hotel
  • 4 floors in hotel
From$60
Average 3.5 /5 Read Reviews Call BookMore Details
Courtyard by Marriott Mahwah - Mahwah
+1-888-469-4795
140 Nj 17, Mahwah, NJ 07430 ~18.45 miles south of Chester
  • Three Star Suburban hotel
  • Gym / Fitness Center Available
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Super 8 Mahwah
+1-888-734-9421
160 State Rt 17 South, Mahwah, NJ 07430 ~18.64 miles south of Chester
  • Economy Highway property
  • Free breakfast available
From$47
Average 3.5 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites Mahwah
+1-888-841-5292
225 Ramapo Valley Rd., Mahwah, NJ 07430 ~18.64 miles south of Chester
  • Affordable Suburban property
  • 86 sleeping rooms in hotel
From$89
Average 3.0 /5 Review Score Call BookMore Details
Super 8 by Wyndham Mahwah in Mahwah
+1-888-455-5160
160 Nj 17 South, Mahwah, NJ 07430 ~18.65 miles south of Chester
  • Inexpensive Highway hotel
  • 3 suites in property
From$65
Average 3.0 /5 Latest Reviews Call BookMore Details
The Roundhouse : 2 East Main St.
+1-888-965-8297
2 East Main St., Beacon, NY 12508 ~18.68 miles northeast of Chester
  • Three Star hotel
  • Hotel has 3 suites
From$90
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
DoubleTree by Hilton Mahwah - Mahwah
+1-888-906-6358
180 Route 17 South, Mahwah, NJ 07430 ~18.69 miles south of Chester
  • Mid-scale Suburban hotel
  • Check in: 3:00 PM
From$105
Average 3.0 /5 Latest Reviews Call BookMore Details
Days Inn by Wyndham Wurtsboro
+1-888-749-6785
21 Perron Dr., Wurtsboro, NY 12790 ~19.05 miles northwest of Chester
  • Inexpensive hotel
  • 32 rooms in property
From$57
Average 3.5 /5 Latest Reviews Call BookMore Details
Days Inn - Mcafee
+1-888-878-9982
15 Rt 94, Mcafee, NJ 07428 ~19.10 miles southwest of Chester
  • Midscale hotel
From$50
Average 3.0 /5 Reviews Call BookMore Details

Next: See My Chester Hotels with Pricing

Bar Chart: Upcoming 20 Days of Chester Hotel Rates

Rates shown are nightly rates before taxes and do not necessarily reflect all Chester, NY discounts available. The chart reflects the cheapest Chester hotel for each day and each star rating category.

When to Go: Harnessing the Best of Chester, NY

Chester, NY boasts a unique blend of weather patterns that make it a destination worth visiting year-round. During the warm summer months, temperatures typically reach up to 83°F, creating perfect conditions for open-air activities and exploration. Visitors can enjoy hiking, biking, or picnicking in the picturesque Goosepond Mountain State Park, or indulge in water sports at nearby lakes. Winter can be quite chilly, with temperatures dipping to as low as 16°F. However, this opens up opportunities for winter sports enthusiasts, with nearby ski resorts offering thrilling slopes and cozy lodges. As fall arrives, the area transforms into a breathtaking palette of colors, making it an ideal season for scenic drives along the Hudson Valley or attending Sugar Loaf Fall Festival. Spring brings mild weather and is the perfect time to explore the charming town. Given its diverse climate patterns, there's no definitive 'best' time to visit Chester. However, if you're keen on experiencing the town's outdoor attractions in their full glory, late spring to early fall would be the most favorable.

Below is a chart of the current pricing seasonality of hotels and motels in Chester, NY:

seasonality of hotel rates in Chester

Averate Rates by Star Rating

Below are 3 charts displaying average price trends by star rating class in Chester, NY. Analyze these illustrations to evaluate the cheapest dates to stay in Chester throughout the year.

Experience Opulence: Luxury and 4-Star Hotels in Chester, NY

If you're looking for somewhere to stay in Chester, NY, there's no shortage of great places that vary from cozy inns to swanky suites. You'll find comfort at every turn, with rooms designed not just for their looks, but also for a good night's sleep. Modern essentials mix with cool conveniences to make staying indoors almost as much fun as going out. Exercise fanatics can hit the gym, food lovers can try out the in-house restaurants, and those in the mood for a pamper can book a spa treatment. During the warmer months, an outdoor pool could be just what you need after a day of exploring. These places don't just promise a comfy bed, they promise a memorable stay in Chester, NY.

Discovering Affordable Comfort: Low-Budget Hotels in Chester

3 Star Average Prices: $112.43

The lovely town of Chester, NY welcomes travelers with a variety of affordable accommodations that cater to all budgetary requirements. From budget-friendly hotels to cozy motels, charming inns, and comfortable suites, Chester offers a range of options for those looking for a low-cost stay. These wallet-friendly lodgings do not compromise on comfort and convenience. Guests can expect essential amenities such as free Wi-Fi, clean and cozy rooms, friendly service, and, often, complimentary breakfast. Some establishments even go the extra mile, boasting additional facilities such as on-site laundry, fitness centers, and shuttle services to major sights. Moreover, these affordable properties are strategically located in close proximity to the major landmarks, trails, and dining spots, ensuring that you're never too far from the action. With a little research, you can find a place that not only fits your budget but also enhances your trip experience.

2 Star Average Prices: $92.57

2 Star Hotel Prices in Chester

Chester's Best Hotel Discounts: Making Your Stay More Affordable

Whatever brings you to this area, you can enjoy significant savings on your accommodation through lodging discounts. For big groups, hotels in Chester, NY offer special group rates and discounted room blocks, ensuring that everyone can stay together and enjoy their time in the town. These deals often come with extra perks such as personalized event planning assistance, dedicated event spaces, and discounted catering options, making group gatherings seamless. Solo travelers can also take advantage of exclusive deals and discounts, allowing them to have a budget-friendly stay without compromising on comfort or quality. In addition to reduced rates, solo travelers may receive additional benefits such as complimentary breakfast, access to onsite fitness centers or pools, and price cuts for local attractions or dining options. These special offers and added benefits make Chester, NY an even more welcoming destination.

Uncover the Fun Side of Chester: Top Activities to Try

Chester, NY is replete with a myriad of attractions that cater to a wide spectrum of interests, promising a memorable experience for every visitor.  Nature lovers will love Goose Pond Mountain. This state park, spread over 1,700 acres, is a lush and pristine natural haven. Its gentle rolling terrain and diverse wildlife make it a favorite among hikers, cyclists, bird watchers, and nature photographers. During fall, the park transforms into a vivid canvas of reds, yellows, and oranges, while winter covers it in snow, making Goose Pond Mountain a year-round destination. Recreational fun awaits at The Castle Fun Center, a family-friendly place that ensures hours of entertainment for kids and adults alike. This sprawling amusement center features a variety of indoor and outdoor activities. From mini-golf and go-karts to roller skating and a state-of-the-art arcade, there is no end to the fun to be had. The Castle Fun Center also houses a thrilling aerial adventure park and a laser maze, adding to the excitement. Each of these attractions, unique in its own right, contributes to the character of Chester, NY and is an indispensable stop on any itinerary to New York's Hudson Valley.

FAQs about hotels in Chester

What are the most favored hotels in Chester?

Courtyard by Marriott, Sleep Inn & Suites Middletown Goshen and Holiday Inn Express & Suites are the best rated hotels based on customer reviews in the last 365 days.

What are the most luxurious hotels in Chester?

Homewood Suites Stewart Airport, The Abbey Inn & Spa and Sheraton Mahwah are the top 3 luxury hotels near Chester city center.

What hotels are closest to the city center of Chester?

Holiday Inn Express & Suites, Sleep Inn & Suites Monroe - Woodbury, and Fairfield Inn & Suites by Marriott Goshen Middletown are the properties closest to Chester city center.

How much does a cheap hotel in Chester cost per night?

In the last year, a 2 star hotel in Chester can be as cheap as $92.57 per night. (based on HotelPlanner prices)

How much does a 3 star hotel in Chester cost per night?

In the last year, the average 3 star hotel in Chester has been $112.43 per night. (based on HotelPlanner prices)

What are the most popular independent hotels in Chester?

Bear Mountain Inn, The Thayer Hotel and The Roundhouse are the best rated independent hotels (not part of a big brand).

What are the best Marriott hotels in Chester?

Courtyard by Marriott, Fairfield Inn & Suites by Marriott Goshen Middletown and Sheraton Mahwah are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

What are the best Choice Hotels branded hotels in Chester?

Sleep Inn & Suites Middletown Goshen, Sleep Inn & Suites Monroe - Woodbury and The Crossroads Hotel - Newburgh, Ascend Hotel Collection are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the most popular IHG hotels in Chester?

Holiday Inn Express & Suites, Holiday Inn Express & Suites Montgomery, an IHG Hotel and Holiday Inn Express West Point, an IHG Hotel are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

Recent traveler guest reviews of Chester, NY

Below are reviews of the city of Chester, NY from an actual visitor's perspective.

"Travel"
Score 5.0 / 5

City of Chester Lots of places to shop , food, clean and all around nice community.

Edward L., from 17-Oct-2019
The average traveler rating of the city of Chester, NY shown above is 5.0 out of 5 based on 1 reviews
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