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 - Chester
+1-888-389-4121
2 Bryle Pl, Chester, NY 10918 +1-888-389-4121
  • Mid-scale Rural hotel
  • 80 rooms in hotel
From£86
Very good 4.0 /5 Reviews Call BookMore Details
Sleep Inn & Suites Monroe - Woodbury
+1-888-675-2083
1 Sleep Way, Monroe, NY 10950 +1-888-675-2083 ~3.82 miles east of Chester
  • Affordable Suburban property
  • 3 floors in hotel
From£70
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
  • Three Star Suburban hotel
  • 3 meeting rooms in hotel
From£59
Very good 4.0 /5 Hotel 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
  • Two-star Lake property
  • Check-in: 3:00pm
From£297
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Harriman Woodbury - Central Valley
+1-888-965-1860
60 Centre Dr., Central Valley, NY 10917 +1-888-965-1860 ~7.62 miles east of Chester
  • Three Star Mountain property
  • Free breakfast available
From£63
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Americas Best Value Inn Central Valley : 139 Route 32
+1-888-788-5576
139 Route 32, Central Valley, NY 10917 +1-888-788-5576 ~7.64 miles east of Chester
  • Cheap Suburban property
  • 45 sleeping rooms in hotel
From£54
Average 3.0 /5 Hotel Reviews Call BookMore Details
Microtel Inn & Suites by Wyndham Middletown - Middletown
+1-888-897-9207
19 Crystal Run Crossing, Middletown, NY 10941 +1-888-897-9207 ~8.14 miles northwest of Chester
  • 2-star Highway property
  • Check in time: 3:00PM
From£57
Very good 4.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott
+1-888-311-4278
24 Crystal Run Crossing, Middletown, NY 10941 +1-888-311-4278 ~8.15 miles northwest of Chester
  • Three Star Suburban property
  • Hotel has 4 floors
From£83
Very good 4.5 /5 Reviews Call BookMore Details
Hampton Inn Middletown Ny
+1-888-469-4795
20 Crystal Run Crossing, Middletown, NY 10941 Website +1-888-469-4795 ~8.19 miles northwest of Chester
  • Two-star Suburban property
  • Fitness / Gym is on-site
From£47
Very good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen
+1-888-734-9421
20 Med Parc Rd., Middletown, NY 10940 +1-888-734-9421 ~8.39 miles northwest of Chester
  • Affordable Downtown hotel
  • 93 rooms in property
From£63
Average 3.0 /5 Guest Reviews Call BookMore Details
Days Inn by Wyndham Middletown in New Hampton
+1-888-841-5292
4939 Route 17 M, New Hampton, NY 10958 +1-888-841-5292 ~8.44 miles west of Chester
  • 2 star Suburban property
  • 39 rooms in property
TRU by Hilton Middletown
+1-888-455-5160
41 Dunning Rd., Middletown, NY 10940 +1-888-455-5160 ~8.76 miles northwest of Chester
  • Low priced property
  • 4 floors in property
From£82
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 +1-888-965-8297 ~9.18 miles northwest of Chester
  • Affordable Suburban property
  • 95 rooms in property
From£86
Very good 4.0 /5 Latest Reviews Call BookMore Details
Super 8 by Wyndham Middletown - Middletown
+1-888-906-6358
563 Route 211 East, Middletown, NY 10940 +1-888-906-6358 ~9.34 miles northwest of Chester
  • Cheap Highway property
  • 82 sleeping rooms in hotel
From£47
Average 3.0 /5 Hotel Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Middletown in Middletown
+1-888-749-6785
551 Route 211 East, Middletown, NY 10941 +1-888-749-6785 ~9.36 miles northwest of Chester
  • Cheap Suburban hotel
  • 85 rooms in hotel
From£38
Very good 4.0 /5 Guest Reviews Call BookMore Details
Residence Inn Middletown Goshen in Middletown
+1-888-878-9982
57 Tower Dr., Middletown, NY 10941 +1-888-878-9982 ~9.45 miles northwest of Chester
  • Mid-scale Suburban property
  • 125 rooms in property
From£63
Average 3.0 /5 Latest Reviews Call BookMore Details
Sleep Inn & Suites Middletown Goshen - Middletown
+1-888-389-4485
3491 Route 6, Middletown, NY 10940 +1-888-389-4485 ~9.61 miles west of Chester
  • Economical Highway property
  • Comp. Breakfast
From£70
Very good 4.5 /5 Reviews Call BookMore Details
Super 8 by Wyndham Montgomery Maybrook in Montgomery
+1-888-389-4121
207 Montgomery Rd., Montgomery, NY 12549 +1-888-389-4121 ~10.78 miles north of Chester
  • Economical Airport property
  • Complimentary breakfast is offered
From£47
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 +1-888-675-2083 ~11.42 miles north of Chester
  • Mid-scale property
From£63
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Montgomery, an IHG Hotel
+1-800-716-8490
2105 State Route 208, Montgomery, NY 12549 +1-800-716-8490 ~11.43 miles north of Chester
  • Affordable Highway property
  • Check in: 03:00 PM
From£76
Very good 4.0 /5 Read Reviews Call BookMore Details
Homewood Suites Stewart Airport
+1-800-805-5223
180 Breunig Rd., New Windsor, NY 12553 Website +1-800-805-5223 ~12.67 miles northeast of Chester
  • Four-star Rural property
  • Gym / Fitness Center Available
From£62
Average 3.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Newburgh Stewart Airport : Homewood Suites 180
+1-888-965-1860
Homewood Suites 180, New Windsor, NY 12553 +1-888-965-1860 ~12.70 miles northeast of Chester
  • 3-star Rural hotel
  • Free comp. breakfast
From£62
Average 3.0 /5 Hotel Reviews Call BookMore Details
Econo Lodge Near Stewart Inter in New Windsor
+1-888-788-5576
310 Windsor Highway, New Windsor, NY 12553 +1-888-788-5576 ~13.42 miles northeast of Chester
  • 2-star Rural property
  • Free comp. breakfast
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 priced property
  • Check-in: 15:00
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
+1-888-311-4278
915 Union Ave. I 84, New Windsor, NY 12553 +1-888-311-4278 ~13.61 miles northeast of Chester
  • Cheap Airport hotel
  • Airport shuttle provided
From£79
Very good 4.0 /5 Guest Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport - Newburgh
+1-888-469-4795
4 Governor Dr., Newburgh, NY 12550 +1-888-469-4795 ~13.85 miles northeast of Chester
  • Mid-scale Rural property
  • Shuttle to airport available
From£90
Average 3.0 /5 Recent Reviews Call BookMore Details
The Crossroads Hotel - Newburgh, Ascend Hotel Collection : 5 Lakeside Rd.
+1-888-734-9421
5 Lakeside Rd., Newburgh, NY 12550 +1-888-734-9421 ~14.07 miles northeast of Chester
  • Affordable Airport hotel
  • 3 floors in property
From£86
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport : 1 Crossroads Court
+1-888-841-5292
1 Crossroads Court, Newburgh, NY 12550 +1-888-841-5292 ~14.20 miles northeast of Chester
  • Affordable Suburban hotel
  • Free breakfast available
From£110
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hudson Valley Hotel and Conference Center by Fairbridge - Newburgh
+1-888-455-5160
90 Rt. 17k, Newburgh, NY 12550 +1-888-455-5160 ~14.35 miles northeast of Chester
  • Low Cost Highway property
  • Gym is available on property
From£67
Poor 2.0 /5 Review Score Call BookMore Details
Howard Johnson by Wyndham Newburgh / West Point in Newburgh
+1-888-965-8297
95 State Route 17k, Newburgh, NY 12550 +1-888-965-8297 ~14.38 miles northeast of Chester
  • Low priced Highway property
  • Free comp. breakfast
Bear Mountain Inn
+1-888-906-6358
3020 Seven Lakes Dr., Bear Mountain, NY 10911 +1-888-906-6358 ~14.46 miles east of Chester
  • Mid-scale Mountain property
  • Free breakfast available
From£118
Very good 4.0 /5 Guest Reviews Call BookMore Details
Ramada by Wyndham Newburgh/West Point : 1289 Route 300
+1-888-749-6785
1289 Route 300, Newburgh, NY 12550 +1-888-749-6785 ~14.57 miles northeast of Chester
  • 2-star Airport hotel
  • Hotel has a green policy Learn more
From£62
Poor 2.0 /5 Reviews Call BookMore Details
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport in Newburgh
+1-888-878-9982
1287 Route 300, Newburgh, NY 12550 +1-888-878-9982 ~14.57 miles northeast of Chester
  • Cheap Airport property
  • Free breakfast
Windsor Motel - New Windsor
+1-888-389-4485
2976 Us Route 9w, New Windsor, NY 12553 +1-888-389-4485 ~14.90 miles northeast of Chester
  • Cheap property
Holiday Inn Express & Suites West Point Fort Montgomery An Ihg in Fort Montgomery
+1-888-389-4121
1106 Rte 9w, Fort Montgomery, NY 10922 +1-888-389-4121 ~14.98 miles east of Chester
  • Midscale property
  • Check-in time: 3:00 PM
From£135
Very good 4.0 /5 Read Reviews Call BookMore Details
FairBridge Inn & Suites at West Point - Highland Falls
+1-888-675-2083
17 Main St., Highland Falls, NY 10928 +1-888-675-2083 ~15.20 miles east of Chester
  • Inexpensive Suburban hotel
  • Check-in time: 3:00pm
From£41
Average 3.0 /5 Latest Reviews Call BookMore Details
The Thayer Hotel in West Point
+1-800-716-8490
674 Thayer Rd., West Point, NY 10996 +1-800-716-8490 ~16.18 miles east of Chester
  • Midscale Suburban hotel
  • 151 rooms in hotel
From£85
Very good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express & Suites Peekskill - Peekskill
+1-800-805-5223
2 John Walsh Blvd., Peekskill, NY 10566 +1-800-805-5223 ~17.78 miles east of Chester
  • Affordable Riverfront hotel
  • 2 meeting rooms in hotel
From£77
Average 3.0 /5 Guest Reviews Call BookMore Details
Inn on the Hudson
+1-888-965-1860
634 Main St., Peekskill, NY 10566 +1-888-965-1860 ~18.05 miles east of Chester
  • Low Cost Riverfront hotel
  • 53 rooms in property
From£86
Average 3.0 /5 Guest Reviews Call BookMore Details
The Abbey Inn & Spa
+1-888-788-5576
900 Fort Hill Rd., Peekskill, NY 10566 +1-888-788-5576 ~18.06 miles east of Chester
  • 4-star Riverfront property
  • Fitness / Gym is on-site
From£397
Average 3.0 /5 Hotel Reviews Call BookMore Details
Crowne Plaza Suffern - Mahwah, an IHG Hotel - Suffern
+1-888-897-9207
3 Executive Blvd., Suffern, NY 10901 +1-888-897-9207 ~18.12 miles southeast of Chester
  • Affordable Suburban property
  • Fitness center on property
From£118
Very good 4.0 /5 Recent Reviews Call BookMore Details
Sheraton Mahwah : 1 International Blvd.
+1-888-311-4278
1 International Blvd., Mahwah, NJ 07495 +1-888-311-4278 ~18.13 miles south of Chester
  • High end Suburban hotel
  • 17 meeting rooms in property
From£102
Average 3.5 /5 Reviews Call BookMore Details
Howard Johnson by Wyndham Suffern
+1-888-469-4795
17 North Airmont Rd., Suffern, NY 10901 +1-888-469-4795 ~18.39 miles southeast of Chester
  • Low Cost Highway property
  • Hotel has 4 floors
From£47
Average 3.5 /5 Hotel Reviews Call BookMore Details
Courtyard by Marriott Mahwah : 140 Nj 17
+1-888-734-9421
140 Nj 17, Mahwah, NJ 07430 +1-888-734-9421 ~18.45 miles south of Chester
  • Three Star Suburban hotel
  • 146 rooms in hotel
From£63
Average 3.0 /5 Latest Reviews Call BookMore Details
Super 8 Mahwah
+1-888-841-5292
160 State Rt 17 South, Mahwah, NJ 07430 +1-888-841-5292 ~18.64 miles south of Chester
  • 2 star Highway property
  • Hotel has 3 floors
From£37
Average 3.5 /5 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 property
  • Fitness center on property
From£70
Average 3.0 /5 Latest Reviews Call BookMore Details
Super 8 by Wyndham Mahwah
+1-888-965-8297
160 Nj 17 South, Mahwah, NJ 07430 +1-888-965-8297 ~18.65 miles south of Chester
  • Economical Highway property
  • 3 floors in hotel
From£51
Average 3.0 /5 Guest Reviews Call BookMore Details
The Roundhouse
+1-888-906-6358
2 East Main St., Beacon, NY 12508 +1-888-906-6358 ~18.68 miles northeast of Chester
  • Three Star property
  • 3 floors in hotel
From£71
Very good 4.0 /5 Reviews Call BookMore Details
Doubletree by Hilton Mahwah
+1-888-749-6785
180 Route 17 South, Mahwah, NJ 07430 +1-888-749-6785 ~18.69 miles south of Chester
  • Three Star Suburban hotel
  • Hotel has 139 rooms
From£83
Average 3.0 /5 Recent Reviews Call BookMore Details
Doubletree
+1-888-878-9982
180 Nj 17, Mahwah, NJ 07430 +1-888-878-9982 ~18.71 miles south of Chester
  • Low-priced hotel
  • Hotel has 14 suites
From£47
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.

"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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