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, Motels & Accommodations

Holiday Inn Express Hotel & Suites Chester by IHG 2 Bryle Pl, Chester, NY 10918 Call
  • Mid-scale Rural hotel
  • 27 suites in hotel
From£82
Very good 4.0 /5 Read Reviews Call BookMore Details
Sleep Inn & Suites Monroe - Woodbury 1 Sleep Way, Monroe, NY 10950 Call ~3.81 miles east of Chester
  • Mid-scale Suburban property
  • Fitness + Health Center
From£67
Very good 4.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott Goshen Middletown 20 Hatfield Lane, Goshen, NY 10924 Call ~4.69 miles northwest of Chester
  • 3 star Suburban property
  • Gym is available on property
From£56
Very good 4.0 /5 Reviews Call BookMore Details
Arrow Park in Monroe 1061 Orange Turnpike, Monroe, NY 10950 Call ~6.40 miles southeast of Chester
  • Cheap Lake hotel
  • Hotel has 11 rooms
From£284
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Harriman Woodbury in Central Valley 60 Centre Dr., Central Valley, NY 10917 Call ~7.61 miles east of Chester
  • 3-star Mountain property
  • Check-in: 3:00pm
From£60
Very good 4.0 /5 Reviews Call BookMore Details
Americas Best Value Inn at Central Valley-Woodbury : 139 Route 32 139 Route 32, Central Valley, NY 10917 Call ~7.62 miles east of Chester
  • Low-priced Suburban property
  • 45 rooms in hotel
From£51
Average 3.0 /5 Guest Reviews Call BookMore Details
Comfort Suites : 100 Estrada Rd. 100 Estrada Rd., Woodbury, NY 10917 Call ~8.10 miles east of Chester
  • Three Star Suburban property
  • Free breakfast
From£109
Average 3.0 /5 Read Reviews Call BookMore Details
Microtel Inn & Suites by Wyndham Middletown 19 Crystal Run Crossing, Middletown, NY 10941 Call ~8.13 miles northwest of Chester
  • Cheap Highway property
  • 3 floors in property
From£54
Very good 4.0 /5 Review Score Call BookMore Details
Courtyard by Marriott 24 Crystal Run Crossing, Middletown, NY 10941 Call ~8.15 miles northwest of Chester
  • Three Star Suburban hotel
  • Hotel has 134 rooms
From£79
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Hampton Inn Middletown Ny - Middletown 20 Crystal Run Crossing, Middletown, NY 10941 Call ~8.18 miles northwest of Chester
  • Cheap Suburban hotel
  • Hotel has 6 suites
From£45
Very good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen - Middletown 20 Med Parc Rd., Middletown, NY 10940 Call ~8.38 miles northwest of Chester
  • Affordable Downtown property
  • 19 suites in property
From£60
Average 3.0 /5 Reviews Call BookMore Details
Days Inn by Wyndham Middletown in New Hampton 4939 Route 17 M, New Hampton, NY 10958 Call ~8.43 miles west of Chester
  • Cheap Suburban property
  • Hotel has 39 rooms
TRU by Hilton Middletown 41 Dunning Rd., Middletown, NY 10940 Call ~8.75 miles northwest of Chester
  • 2 star hotel
  • 104 rooms in hotel
From£78
Average 3.0 /5 Review Score Call BookMore Details
Home2 Suites by Hilton Middletown - Middletown 600 Route 211 East, Middletown, NY 10941 Call ~9.17 miles northwest of Chester
  • Mid-scale Suburban hotel
  • Hotel has 5 floors
From£82
Very good 4.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Middletown : 563 Route 211 East 563 Route 211 East, Middletown, NY 10940 Call ~9.33 miles northwest of Chester
  • Two-star Highway property
  • Comp. Breakfast
From£45
Average 3.0 /5 Hotel Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Middletown : 551 Route 211 East 551 Route 211 East, Middletown, NY 10941 Call ~9.34 miles northwest of Chester
  • Two-star Suburban property
  • 3 suites in property
From£36
Very good 4.0 /5 Reviews Call BookMore Details
Residence Inn Middletown Goshen in Middletown 57 Tower Dr., Middletown, NY 10941 Call ~9.43 miles northwest of Chester
  • Affordable Suburban property
  • Check in: 3:00PM
From£60
Average 3.0 /5 Reviews Call BookMore Details
Sleep Inn & Suites Middletown Goshen 3491 Route 6, Middletown, NY 10940 Call ~9.60 miles west of Chester
  • Cheap Highway hotel
  • 34 suites in property
From£67
Very good 4.5 /5 Read Reviews Call BookMore Details
Super 8 by Wyndham Montgomery Maybrook in Montgomery 207 Montgomery Rd., Montgomery, NY 12549 Call ~10.77 miles north of Chester
  • Low-priced Airport property
  • Check in: 3:00pm
From£45
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery, an IHG Hotel 2105 Ny 208, Montgomery, NY 12549 Call ~11.40 miles north of Chester
  • Midscale hotel
From£60
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery by IHG 2105 State Route 208, Montgomery, NY 12549 Call ~11.41 miles north of Chester
  • 3-star Highway property
  • Free comp. breakfast
From£72
Very good 4.0 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Newburgh Stewart Airport 180 Breunig Rd., New Windsor, NY 12553 Website Call ~12.66 miles northeast of Chester
  • Four star Rural hotel
  • Fitness + Health Center
From£59
Average 3.0 /5 Guest Reviews Call BookMore Details
Countryside Inn & Suites : 310 Windsor Highway 310 Windsor Highway, New Windsor, NY 12553 Call ~13.41 miles northeast of Chester
  • Cheap Rural hotel
  • Check in: 3:00pm
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point : 915 Union Ave. I 84 915 Union Ave. I 84, New Windsor, NY 12553 Call ~13.60 miles northeast of Chester
  • 2 star Airport hotel
  • Check-in: 3:00 PM
From£75
Very good 4.0 /5 Read Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport 4 Governor Dr., Newburgh, NY 12550 Call ~13.84 miles northeast of Chester
  • Midscale Rural property
  • 78 rooms in hotel
From£86
Average 3.0 /5 Reviews Call BookMore Details
The Crossroads Hotel, Newburgh 5 Lakeside Rd., Newburgh, NY 12550 Call ~14.06 miles northeast of Chester
  • Mid-scale Airport hotel
  • Hotel has 124 rooms
From£82
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport 1 Crossroads Court, Newburgh, NY 12550 Call ~14.18 miles northeast of Chester
  • Affordable Suburban hotel
  • Free comp. breakfast
From£105
Very good 4.0 /5 Guest Reviews Call BookMore Details
Overlook Lodge at Bear Mountain - Bear Mountain 55 Hessian Dr., Bear Mountain, NY 10911 Call ~14.25 miles east of Chester
  • 3-star Mountain property
  • 2 conference rooms in property
From£30
Average 3.5 /5 Latest Reviews Call BookMore Details
Hudson Valley Hotel and Conference Center by Fairbridge 90 Rt. 17k, Newburgh, NY 12550 Call ~14.33 miles northeast of Chester
  • Two star Highway property
  • Hotel has 80 rooms
From£64
Poor 2.0 /5 Read Reviews Call BookMore Details
Howard Johnson by Wyndham Newburgh / West Point 95 State Route 17k, Newburgh, NY 12550 Call ~14.37 miles northeast of Chester
  • Two-star Highway property
  • Free breakfast available
Bear Mountain Inn in Bear Mountain 3020 Seven Lakes Dr., Bear Mountain, NY 10911 Call ~14.43 miles east of Chester
  • 3-star Mountain property
  • 3 suites in property
From£112
Very good 4.0 /5 Latest Reviews Call BookMore Details
Ramada by Wyndham Newburgh / West Point 1289 Route 300, Newburgh, NY 12550 Call ~14.55 miles northeast of Chester
  • 2-star Airport hotel
  • Gym / Fitness Center Available
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport in Newburgh 1287 Route 300, Newburgh, NY 12550 Call ~14.55 miles northeast of Chester
  • Low-priced Airport property
  • Check-in time: 3:00PM
Windsor Motel 2976 Us Route 9w, New Windsor, NY 12553 Call ~14.88 miles northeast of Chester
  • Two-star property
  • Hotel has 28 rooms
Holiday Inn Express West Point by IHG : 1106 Rte 9w 1106 Rte 9w, Fort Montgomery, NY 10922 Call ~14.96 miles east of Chester
  • Midscale property
  • Check in time: 3:00 PM
From£128
Very good 4.0 /5 Recent Reviews Call BookMore Details
Fairbridge Inn & Suites at West Point 17 Main St., Highland Falls, NY 10928 Call ~15.17 miles east of Chester
  • Low Cost Suburban hotel
  • Free breakfast
From£39
Average 3.0 /5 Read Reviews Call BookMore Details
The Thayer Hotel at West Point in West Point 674 Thayer Rd., West Point, NY 10996 Call ~15.80 miles east of Chester
  • Three Star Suburban property
  • Check in: 4:00 PM
From£81
Very good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill 2 John Walsh Blvd., Peekskill, NY 10566 Call ~17.74 miles east of Chester
  • Mid-scale Riverfront hotel
  • Fitness / Gym is on-site
From£73
Average 3.0 /5 Hotel Reviews Call BookMore Details
Inn on the Hudson - Peekskill 634 Main St., Peekskill, NY 10566 Call ~18.02 miles east of Chester
  • Cheap Riverfront property
  • Free breakfast
From£82
Average 3.0 /5 Recent Reviews Call BookMore Details
The Abbey Inn & Spa 900 Fort Hill Rd., Peekskill, NY 10566 Call ~18.02 miles east of Chester
  • 4 star Riverfront property
  • 42 rooms in hotel
From£378
Average 3.0 /5 Reviews Call BookMore Details
Sheraton Mahwah 1 International Blvd., Mahwah, NJ 07495 Call ~18.10 miles south of Chester
  • High-end Suburban hotel
  • 17 meeting rooms in hotel
From£97
Average 3.5 /5 Hotel Reviews Call BookMore Details
Crowne Plaza Suffern Mahwah by Ihg Three Executive Blvd., Suffern, NY 10901 Call ~18.13 miles southeast of Chester
  • 3-star Suburban hotel
  • Hotel has 243 rooms
From£49
Very good 4.0 /5 Read Reviews Call BookMore Details
Howard Johnson by Wyndham Suffern 17 North Airmont Rd., Suffern, NY 10901 Call ~18.36 miles southeast of Chester
  • 2-star Highway hotel
  • Hotel has 4 floors
From£45
Average 3.5 /5 Guest Reviews Call BookMore Details
Courtyard by Marriott Mahwah in Mahwah 140 Nj 17, Mahwah, NJ 07430 Call ~18.42 miles south of Chester
  • Three Star Suburban hotel
  • 2 meeting rooms in hotel
From£60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Super 8 Mahwah in Mahwah 160 State Rt 17 South, Mahwah, NJ 07430 Call ~18.61 miles south of Chester
  • Cheap Highway property
  • Check in: 3:00pm
From£35
Average 3.5 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites Mahwah : 225 Ramapo Valley Rd. 225 Ramapo Valley Rd., Mahwah, NJ 07430 Call ~18.61 miles south of Chester
  • 3-star Suburban hotel
  • Free comp. breakfast
From£67
Average 3.0 /5 Recent Reviews Call BookMore Details
Super 8 by Wyndham Mahwah 160 Nj 17 South, Mahwah, NJ 07430 Call ~18.62 miles south of Chester
  • Economical Highway hotel
  • Hotel has 3 suites
From£49
Average 3.0 /5 Recent Reviews Call BookMore Details
Doubletree by Hilton Mahwah 180 Route 17 South, Mahwah, NJ 07430 Call ~18.66 miles south of Chester
  • Three Star Suburban property
  • Hotel has an eco-friendly policy See policy
From£79
Average 3.0 /5 Guest Reviews Call BookMore Details
The Roundhouse 2 East Main St., Beacon, NY 12508 Call ~18.67 miles northeast of Chester
  • Midscale property
  • Hotel has 3 suites
From£68
Very good 4.0 /5 Reviews Call BookMore Details
Doubletree 180 Nj 17, Mahwah, NJ 07430 Call ~18.68 miles south of Chester
  • Inexpensive property
  • 5 meeting rooms in property
From£45
Average 3.0 /5 Review Score Call BookMore Details

Next: See My Chester Hotels with Pricing

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.

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.

Recent traveler guest reviews of Chester, NY

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

"Tin barn brewery"
Score 4.0 / 5

Erney M., from 03-Mar-2026
"Proximity to Campbell Hall."
Score 5.0 / 5

I was in Campbell Hall for a communion.

Steven L., from 08-May-2025
"SLPAC and WOODBURY COMMONS"
Score 4.0 / 5

SLPAC and WOODBURY COMMONS

Joann H., from 29-Mar-2025
"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
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