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
  • Affordable Rural hotel
  • Hotel has 3 floors
From$109
Very Good 4.0 /5 Review Score Call BookMore Details
Sleep Inn & Suites Monroe - Woodbury 1 Sleep Way, Monroe, NY 10950 Call ~3.81 miles east of Chester
  • Midscale Suburban property
  • 6 suites in hotel
From$89
Very Good 4.0 /5 Hotel Reviews 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 hotel
  • 3 floors in hotel
From$75
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
  • Economy Lake property
  • Hotel has 11 rooms
From$375
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn Harriman Woodbury 60 Centre Dr., Central Valley, NY 10917 Call ~7.61 miles east of Chester
  • Midscale Mountain hotel
  • 136 rooms in hotel
From$80
Very Good 4.0 /5 Review Score Call BookMore Details
Americas Best Value Inn at Central Valley-Woodbury 139 Route 32, Central Valley, NY 10917 Call ~7.62 miles east of Chester
  • Inexpensive Suburban property
  • Check-in time: 01.00 PM
From$68
Average 3.0 /5 Hotel Reviews Call BookMore Details
Comfort Suites 100 Estrada Rd., Woodbury, NY 10917 Call ~8.10 miles east of Chester
  • 3-star Suburban property
  • Free breakfast
From$145
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 hotel
  • 3 floors in hotel
From$72
Very Good 4.0 /5 Read Reviews Call BookMore Details
Courtyard by Marriott in Middletown 24 Crystal Run Crossing, Middletown, NY 10941 Call ~8.15 miles northwest of Chester
  • 3 star Suburban hotel
  • Check in time: 3:00pm
From$105
Very Good 4.5 /5 Reviews Call BookMore Details
Hampton Inn Middletown Ny in Middletown 20 Crystal Run Crossing, Middletown, NY 10941 Call ~8.18 miles northwest of Chester
  • Cheap Suburban property
  • Hotel has 4 floors
From$60
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen 20 Med Parc Rd., Middletown, NY 10940 Call ~8.38 miles northwest of Chester
  • 3-star Downtown hotel
  • 93 rooms in hotel
From$80
Average 3.0 /5 Reviews Call BookMore Details
Days Inn by Wyndham Middletown 4939 Route 17 M, New Hampton, NY 10958 Call ~8.43 miles west of Chester
  • Two star Suburban property
  • Check-in time: 1pm
TRU by Hilton Middletown - Middletown 41 Dunning Rd., Middletown, NY 10940 Call ~8.75 miles northwest of Chester
  • 2-star hotel
  • 4 floors in property
From$104
Average 3.0 /5 Read Reviews Call BookMore Details
Home2 Suites by Hilton Middletown 600 Route 211 East, Middletown, NY 10941 Call ~9.17 miles northwest of Chester
  • Midscale Suburban property
  • Check in time: 15:00
From$109
Very Good 4.0 /5 Recent 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
  • 2-star Highway property
  • 82 rooms in hotel
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Middletown 551 Route 211 East, Middletown, NY 10941 Call ~9.34 miles northwest of Chester
  • Cheap Suburban hotel
  • 3 suites in hotel
From$48
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn Middletown Goshen in Middletown 57 Tower Dr., Middletown, NY 10941 Call ~9.43 miles northwest of Chester
  • 3 star Suburban hotel
  • Access to gym on-site
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Sleep Inn & Suites Middletown Goshen 3491 Route 6, Middletown, NY 10940 Call ~9.60 miles west of Chester
  • 2 star Highway property
  • Complimentary breakfast is offered
From$89
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Super 8 by Wyndham Montgomery Maybrook 207 Montgomery Rd., Montgomery, NY 12549 Call ~10.77 miles north of Chester
  • Two-star Airport hotel
  • Complimentary breakfast is offered
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery, an IHG Hotel - Montgomery 2105 Ny 208, Montgomery, NY 12549 Call ~11.40 miles north of Chester
  • Midscale property
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery by IHG : 2105 State Route 208 2105 State Route 208, Montgomery, NY 12549 Call ~11.41 miles north of Chester
  • 3 star Highway property
  • Check-in time: 03:00 PM
From$96
Very Good 4.0 /5 Recent 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
  • High-end Rural hotel
  • Comp. Breakfast
From$79
Average 3.0 /5 Review Score Call BookMore Details
Countryside Inn & Suites 310 Windsor Highway, New Windsor, NY 12553 Call ~13.41 miles northeast of Chester
  • 2-star Rural property
  • 2 floors in property
From$60
Poor 2.0 /5 Reviews Call BookMore Details
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 915 Union Ave. I 84, New Windsor, NY 12553 Call ~13.60 miles northeast of Chester
  • Two-star Airport property
  • Shuttle from airport available
From$100
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport 4 Governor Dr., Newburgh, NY 12550 Call ~13.84 miles northeast of Chester
  • Affordable Rural property
  • Shuttle to airport available
From$114
Average 3.0 /5 Review Score Call BookMore Details
The Crossroads Hotel, Newburgh 5 Lakeside Rd., Newburgh, NY 12550 Call ~14.06 miles northeast of Chester
  • Midscale Airport hotel
  • Airport shuttle provided
From$109
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport 1 Crossroads Court, Newburgh, NY 12550 Call ~14.18 miles northeast of Chester
  • Midscale Suburban property
  • Shuttle to airport available
From$139
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Overlook Lodge at Bear Mountain : 55 Hessian Dr. 55 Hessian Dr., Bear Mountain, NY 10911 Call ~14.25 miles east of Chester
  • Midscale Mountain hotel
  • Check in time: 1:00 PM
From$40
Average 3.5 /5 Guest Reviews Call BookMore Details
Hudson Valley Hotel and Conference Center by Fairbridge - Newburgh 90 Rt. 17k, Newburgh, NY 12550 Call ~14.33 miles northeast of Chester
  • Low-priced Highway hotel
  • 2 floors in property
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 comp. breakfast
Bear Mountain Inn : 3020 Seven Lakes Dr. 3020 Seven Lakes Dr., Bear Mountain, NY 10911 Call ~14.43 miles east of Chester
  • Affordable Mountain hotel
  • Hotel has 3 suites
From$149
Very Good 4.0 /5 Review Score Call BookMore Details
Ramada by Wyndham Newburgh / West Point - Newburgh 1289 Route 300, Newburgh, NY 12550 Call ~14.55 miles northeast of Chester
  • Low-priced Airport hotel
  • Hotel has a green policy Learn more
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
  • Two-star Airport property
  • Airport shuttle available
From$60
Poor 2.0 /5 Reviews Call BookMore Details
Windsor Motel - New Windsor 2976 Us Route 9w, New Windsor, NY 12553 Call ~14.88 miles northeast of Chester
  • Low priced property
  • Check-in: 2:00 P.M
Holiday Inn Express West Point by IHG in Fort Montgomery 1106 Rte 9w, Fort Montgomery, NY 10922 Call ~14.96 miles east of Chester
  • 3 star property
From$170
Very Good 4.0 /5 Review Score Call BookMore Details
FairBridge Inn & Suites at West Point 17 Main St., Highland Falls, NY 10928 Call ~15.17 miles east of Chester
  • Cheap Suburban property
  • 2 floors in property
From$52
Average 3.0 /5 Latest Reviews Call BookMore Details
The Thayer Hotel at West Point 674 Thayer Rd., West Point, NY 10996 Call ~15.80 miles east of Chester
  • Mid-scale Suburban hotel
  • Hotel has 5 floors
From$108
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill 2 John Walsh Blvd., Peekskill, NY 10566 Call ~17.74 miles east of Chester
  • Three Star Riverfront hotel
  • Access to gym on-site
From$97
Average 3.0 /5 Recent Reviews Call BookMore Details
Inn on the Hudson 634 Main St., Peekskill, NY 10566 Call ~18.02 miles east of Chester
  • Low priced Riverfront hotel
  • 53 rooms in hotel
From$109
Average 3.0 /5 Reviews Call BookMore Details
The Abbey Inn & Spa 900 Fort Hill Rd., Peekskill, NY 10566 Call ~18.02 miles east of Chester
  • Four star Riverfront property
  • Check in: 3:00 PM
From$500
Average 3.0 /5 Reviews Call BookMore Details
Sheraton Mahwah 1 International Blvd., Mahwah, NJ 07495 Call ~18.10 miles south of Chester
  • Four-star Suburban hotel
  • Has environment-friendly policy Read more
From$129
Average 3.5 /5 Latest Reviews Call BookMore Details
Crowne Plaza Suffern Mahwah by Ihg - Suffern Three Executive Blvd., Suffern, NY 10901 Call ~18.13 miles southeast of Chester
  • Mid-scale Suburban property
  • Check-in time: 3:00 pm
From$65
Very Good 4.0 /5 Read Reviews Call BookMore Details
Howard Johnson by Wyndham Suffern in Suffern 17 North Airmont Rd., Suffern, NY 10901 Call ~18.36 miles southeast of Chester
  • Low-priced Highway hotel
  • Fitness + Health Center
From$60
Average 3.5 /5 Reviews Call BookMore Details
Courtyard by Marriott Mahwah 140 Nj 17, Mahwah, NJ 07430 Call ~18.42 miles south of Chester
  • Midscale Suburban property
  • 12 suites in hotel
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Super 8 Mahwah in Mahwah 160 State Rt 17 South, Mahwah, NJ 07430 Call ~18.61 miles south of Chester
  • Low priced Highway hotel
  • 78 rooms in hotel
From$47
Average 3.5 /5 Read Reviews Call BookMore Details
Fairfield Inn & Suites Mahwah in Mahwah 225 Ramapo Valley Rd., Mahwah, NJ 07430 Call ~18.61 miles south of Chester
  • Affordable Suburban hotel
  • 86 rooms in hotel
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Mahwah 160 Nj 17 South, Mahwah, NJ 07430 Call ~18.62 miles south of Chester
  • 2-star Highway hotel
  • Check-in time: 3pm
From$65
Average 3.0 /5 Hotel Reviews Call BookMore Details
Doubletree by Hilton Mahwah : 180 Route 17 South 180 Route 17 South, Mahwah, NJ 07430 Call ~18.66 miles south of Chester
  • 3-star Suburban hotel
  • 12 suites in property
From$105
Average 3.0 /5 Guest Reviews Call BookMore Details
The Roundhouse - Beacon 2 East Main St., Beacon, NY 12508 Call ~18.67 miles northeast of Chester
  • Affordable hotel
  • 3 floors in property
From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Doubletree 180 Nj 17, Mahwah, NJ 07430 Call ~18.68 miles south of Chester
  • Low Cost hotel
  • Fitness + Health Center
From$60
Average 3.0 /5 Latest Reviews 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.

"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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