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 & Suites
+1-888-389-4121
2 Bryle Pl, Chester, NY 10918 +1-888-389-4121
  • Midscale Rural hotel
  • Hotel has an eco-friendly policy See policy
From£81
Very good 4.0 /5 Recent Reviews Call BookMore Details
Sleep Inn & Suites Monroe - Woodbury : 1 Sleep Way
+1-888-675-2083
1 Sleep Way, Monroe, NY 10950 +1-888-675-2083 ~3.82 miles east of Chester
  • Three Star Suburban hotel
  • 64 sleeping rooms in hotel
From£66
Very good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Goshen Middletown : 20 Hatfield Lane
+1-800-716-8490
20 Hatfield Lane, Goshen, NY 10924 +1-800-716-8490 ~4.70 miles northwest of Chester
  • 3 star Suburban hotel
  • 95 rooms in property
From£56
Very good 4.0 /5 Latest Reviews Call BookMore Details
Arrow Park - Monroe
+1-800-805-5223
1061 Orange Turnpike, Monroe, NY 10950 +1-800-805-5223 ~6.41 miles southeast of Chester
  • Low Cost Lake property
  • Hotel has 11 rooms
From£280
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Harriman Woodbury
+1-888-965-1860
60 Centre Dr., Central Valley, NY 10917 +1-888-965-1860 ~7.62 miles east of Chester
  • Midscale Mountain property
  • Fitness / Gym is on-site
From£59
Very good 4.0 /5 Recent Reviews Call BookMore Details
Americas Best Value Inn at Central Valley-Woodbury in Central Valley
+1-888-788-5576
139 Route 32, Central Valley, NY 10917 +1-888-788-5576 ~7.64 miles east of Chester
  • Low priced Suburban hotel
  • Check in time: 01.00 PM
From£50
Average 3.0 /5 Guest Reviews Call BookMore Details
Comfort Suites
+1-888-897-9207
100 Estrada Rd., Woodbury, NY 10917 +1-888-897-9207 ~8.11 miles east of Chester
  • 3 star Suburban property
  • 85 rooms in property
From£108
Average 3.0 /5 Hotel Reviews Call BookMore Details
Microtel Inn & Suites by Wyndham Middletown - Middletown
+1-888-311-4278
19 Crystal Run Crossing, Middletown, NY 10941 +1-888-311-4278 ~8.14 miles northwest of Chester
  • Low-priced Highway hotel
  • Hotel has 3 floors
From£53
Very good 4.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott in Middletown
+1-888-469-4795
24 Crystal Run Crossing, Middletown, NY 10941 +1-888-469-4795 ~8.15 miles northwest of Chester
  • Mid-scale Suburban property
  • 134 rooms in property
From£78
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Hampton Inn Middletown Ny : 20 Crystal Run Crossing
+1-888-734-9421
20 Crystal Run Crossing, Middletown, NY 10941 Website +1-888-734-9421 ~8.19 miles northwest of Chester
  • Low priced Suburban property
  • 4 floors in property
From£44
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen : 20 Med Parc Rd.
+1-888-841-5292
20 Med Parc Rd., Middletown, NY 10940 +1-888-841-5292 ~8.39 miles northwest of Chester
  • Affordable Downtown hotel
  • Free breakfast available
From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Days Inn by Wyndham Middletown : 4939 Route 17 M
+1-888-455-5160
4939 Route 17 M, New Hampton, NY 10958 +1-888-455-5160 ~8.44 miles west of Chester
  • Two-star Suburban hotel
  • Check-in time: 1pm
TRU by Hilton Middletown
+1-888-965-8297
41 Dunning Rd., Middletown, NY 10940 +1-888-965-8297 ~8.76 miles northwest of Chester
  • 2-star hotel
  • Check-in: 15:00
From£77
Average 3.0 /5 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Middletown
+1-888-906-6358
600 Route 211 East, Middletown, NY 10941 +1-888-906-6358 ~9.18 miles northwest of Chester
  • Midscale Suburban hotel
  • 5 floors in hotel
From£81
Very good 4.0 /5 Review Score Call BookMore Details
Super 8 by Wyndham Middletown
+1-888-749-6785
563 Route 211 East, Middletown, NY 10940 +1-888-749-6785 ~9.34 miles northwest of Chester
  • Low-priced Highway hotel
  • 2 floors in property
From£44
Average 3.0 /5 Recent Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Middletown : 551 Route 211 East
+1-888-878-9982
551 Route 211 East, Middletown, NY 10941 +1-888-878-9982 ~9.36 miles northwest of Chester
  • 2-star Suburban property
  • Hotel has 85 rooms
From£35
Very good 4.0 /5 Guest Reviews Call BookMore Details
Residence Inn Middletown Goshen
+1-888-389-4485
57 Tower Dr., Middletown, NY 10941 +1-888-389-4485 ~9.45 miles northwest of Chester
  • 3-star Suburban hotel
  • 4 floors in hotel
From£59
Average 3.0 /5 Hotel Reviews Call BookMore Details
Sleep Inn & Suites Middletown Goshen - Middletown
+1-888-389-4121
3491 Route 6, Middletown, NY 10940 +1-888-389-4121 ~9.61 miles west of Chester
  • Economy Highway property
  • 4 floors in hotel
From£66
Very good 4.5 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Montgomery Maybrook : 207 Montgomery Rd.
+1-888-675-2083
207 Montgomery Rd., Montgomery, NY 12549 +1-888-675-2083 ~10.78 miles north of Chester
  • 2-star Airport property
  • Check-in time: 3:00pm
From£44
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery, an IHG Hotel
+1-800-716-8490
2105 Ny 208, Montgomery, NY 12549 +1-800-716-8490 ~11.42 miles north of Chester
  • 3-star property
From£59
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery by IHG - Montgomery
+1-800-805-5223
2105 State Route 208, Montgomery, NY 12549 +1-800-805-5223 ~11.43 miles north of Chester
  • 3-star Highway hotel
  • 29 suites in property
From£71
Very good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Newburgh Stewart Airport
+1-888-965-1860
180 Breunig Rd., New Windsor, NY 12553 Website +1-888-965-1860 ~12.67 miles northeast of Chester
  • 4 star Rural property
  • Complimentary breakfast is offered
From£59
Average 3.0 /5 Latest Reviews Call BookMore Details
Econo Lodge Near Stewart Inter
+1-888-788-5576
310 Windsor Highway, New Windsor, NY 12553 +1-888-788-5576 ~13.42 miles northeast of Chester
  • Cheap Rural hotel
  • Free complimentary breakfast
From£44
Poor 2.0 /5 Review Score Call BookMore Details
Econo Lodge Near Stewart Inter - New Windsor
+1-888-897-9207
310 Windsor Highway Sr 32, New Windsor, NY 12550 +1-888-897-9207 ~13.44 miles northeast of Chester
  • Low Cost property
  • Free comp. breakfast
From£44
Poor 2.0 /5 Read Reviews Call BookMore Details
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point : 915 Union Ave. I 84
+1-888-311-4278
915 Union Ave. I 84, New Windsor, NY 12553 +1-888-311-4278 ~13.61 miles northeast of Chester
  • 2-star Airport hotel
  • 2 floors in hotel
From£74
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport : 4 Governor Dr.
+1-888-469-4795
4 Governor Dr., Newburgh, NY 12550 +1-888-469-4795 ~13.85 miles northeast of Chester
  • 3-star Rural hotel
  • Airport shuttle available
From£85
Average 3.0 /5 Hotel Reviews Call BookMore Details
The Crossroads Hotel, Newburgh
+1-888-734-9421
5 Lakeside Rd., Newburgh, NY 12550 +1-888-734-9421 ~14.07 miles northeast of Chester
  • 3-star Airport hotel
  • 3 suites in hotel
From£81
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport - Newburgh
+1-888-841-5292
1 Crossroads Court, Newburgh, NY 12550 +1-888-841-5292 ~14.20 miles northeast of Chester
  • Three Star Suburban property
  • 4 meeting rooms in hotel
From£103
Very good 4.0 /5 Guest Reviews Call BookMore Details
Overlook Lodge at Bear Mountain - Bear Mountain
+1-888-455-5160
55 Hessian Dr., Bear Mountain, NY 10911 +1-888-455-5160 ~14.27 miles east of Chester
  • 3 star Mountain property
  • Check-in: 1:00 PM
From£29
Average 3.5 /5 Hotel Reviews Call BookMore Details
Hudson Valley Hotel and Conference Center by Fairbridge
+1-888-965-8297
90 Rt. 17k, Newburgh, NY 12550 +1-888-965-8297 ~14.35 miles northeast of Chester
  • Economical Highway hotel
  • 2 floors in hotel
Howard Johnson by Wyndham Newburgh / West Point
+1-888-906-6358
95 State Route 17k, Newburgh, NY 12550 +1-888-906-6358 ~14.38 miles northeast of Chester
  • Two-star Highway hotel
  • Free comp. breakfast
From£44
Poor 2.5 /5 Reviews Call BookMore Details
Bear Mountain Inn in Bear Mountain
+1-888-749-6785
3020 Seven Lakes Dr., Bear Mountain, NY 10911 +1-888-749-6785 ~14.46 miles east of Chester
  • Three Star Mountain property
  • Hotel has 63 rooms
From£111
Very good 4.0 /5 Latest Reviews Call BookMore Details
Ramada by Wyndham Newburgh / West Point
+1-888-878-9982
1289 Route 300, Newburgh, NY 12550 +1-888-878-9982 ~14.57 miles northeast of Chester
  • Inexpensive Airport hotel
  • 35 suites in hotel
From£59
Poor 2.0 /5 Reviews Call BookMore Details
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
+1-888-389-4485
1287 Route 300, Newburgh, NY 12550 +1-888-389-4485 ~14.57 miles northeast of Chester
  • Low Cost Airport property
  • Airport shuttle available
Windsor Motel in New Windsor
+1-888-389-4121
2976 Us Route 9w, New Windsor, NY 12553 +1-888-389-4121 ~14.90 miles northeast of Chester
  • Cheap property
From£44
Poor 2.5 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites West Point Fort Montgomery An Ihg
+1-888-675-2083
1106 Rte 9w, Fort Montgomery, NY 10922 +1-888-675-2083 ~14.98 miles east of Chester
  • Midscale property
  • Check-in: 3:00 PM
From£127
Very good 4.0 /5 Review Score Call BookMore Details
FairBridge Inn & Suites at West Point in Highland Falls
+1-800-716-8490
17 Main St., Highland Falls, NY 10928 +1-800-716-8490 ~15.20 miles east of Chester
  • Economy Suburban hotel
  • 2 floors in hotel
From£38
Average 3.0 /5 Read Reviews Call BookMore Details
The Thayer Hotel
+1-800-805-5223
674 Thayer Rd., West Point, NY 10996 +1-800-805-5223 ~16.18 miles east of Chester
  • Mid-scale Suburban property
  • 4 meeting rooms in hotel
From£80
Very good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill : 2 John Walsh Blvd.
+1-888-965-1860
2 John Walsh Blvd., Peekskill, NY 10566 +1-888-965-1860 ~17.78 miles east of Chester
  • 3-star Riverfront property
  • Free comp. breakfast
From£72
Average 3.0 /5 Latest Reviews Call BookMore Details
Inn on the Hudson in Peekskill
+1-888-788-5576
634 Main St., Peekskill, NY 10566 +1-888-788-5576 ~18.05 miles east of Chester
  • Economical Riverfront hotel
  • Complimentary breakfast is offered
From£81
Average 3.0 /5 Latest Reviews Call BookMore Details
The Abbey Inn & Spa - Peekskill
+1-888-897-9207
900 Fort Hill Rd., Peekskill, NY 10566 +1-888-897-9207 ~18.06 miles east of Chester
  • High-end Riverfront hotel
  • Check-in: 3:00 PM
From£373
Average 3.0 /5 Read Reviews Call BookMore Details
Crowne Plaza Suffern - Mahwah by IHG
+1-888-311-4278
3 Executive Blvd., Suffern, NY 10901 +1-888-311-4278 ~18.12 miles southeast of Chester
  • Three Star Suburban property
  • Check in: 3:00pm
From£111
Very good 4.0 /5 Read Reviews Call BookMore Details
Sheraton Mahwah - Mahwah
+1-888-469-4795
1 International Blvd., Mahwah, NJ 07495 +1-888-469-4795 ~18.13 miles south of Chester
  • Four star Suburban hotel
  • Hotel has 225 rooms
From£96
Average 3.5 /5 Hotel Reviews Call BookMore Details
Howard Johnson by Wyndham Suffern
+1-888-734-9421
17 North Airmont Rd., Suffern, NY 10901 +1-888-734-9421 ~18.39 miles southeast of Chester
  • Low Cost Highway property
  • Fitness center on property
From£44
Average 3.5 /5 Reviews Call BookMore Details
Courtyard by Marriott Mahwah : 140 Nj 17
+1-888-841-5292
140 Nj 17, Mahwah, NJ 07430 +1-888-841-5292 ~18.45 miles south of Chester
  • Midscale Suburban property
  • 146 sleeping rooms in hotel
From£59
Average 3.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites Mahwah - Mahwah
+1-888-455-5160
225 Ramapo Valley Rd., Mahwah, NJ 07430 +1-888-455-5160 ~18.64 miles south of Chester
  • 3 star Suburban hotel
  • Hotel has 86 rooms
From£66
Average 3.0 /5 Latest Reviews Call BookMore Details
Super 8 Mahwah
+1-888-965-8297
160 State Rt 17 South, Mahwah, NJ 07430 +1-888-965-8297 ~18.64 miles south of Chester
  • 2-star Highway hotel
  • 78 sleeping rooms in hotel
From£35
Average 3.5 /5 Latest Reviews Call BookMore Details
Super 8 by Wyndham Mahwah
+1-888-906-6358
160 Nj 17 South, Mahwah, NJ 07430 +1-888-906-6358 ~18.65 miles south of Chester
  • Two star Highway hotel
  • Check in time: 3pm
From£48
Average 3.0 /5 Reviews Call BookMore Details
The Roundhouse in Beacon
+1-888-749-6785
2 East Main St., Beacon, NY 12508 +1-888-749-6785 ~18.68 miles northeast of Chester
  • Affordable property
  • 41 rooms in property
From£67
Very good 4.0 /5 Read Reviews Call BookMore Details
Doubletree by Hilton Mahwah
+1-888-878-9982
180 Route 17 South, Mahwah, NJ 07430 +1-888-878-9982 ~18.69 miles south of Chester
  • Three Star Suburban hotel
  • 12 suites in hotel
From£78
Average 3.0 /5 Recent 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.

"SLPAC and WOODBURY COMMONS"
Score 4.0 / 5

SLPAC and WOODBURY COMMONS

Joann H., from 29-Mar-2025
""
Score 5.0 / 5

I loved the scenery in the area. Its nice to go somewhere there are still many trees and ponds. A lovely place. I would like to live somewhere like that. It was only a half hour away from my destination which was the Jehovah's Witness Headquarters Office Tour.

Deanna M., from 07-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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