Chester Hotels with Pools - Outdoor/Indoor Pools in Chester NY

Chester hotels and motels with swimming pools that are perfect for a family are listed below. Search for cheap and discount hotel rates at hotels with a pool in or near Chester, NY for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Chester New York hotel and motel rooms for children. Review the list of Chester hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.
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Chester Hotels with Outdoor or Indoor Pools

Holiday Inn Express Hotel & Suites Chester by IHG 2 Bryle Pl, Chester, NY 10918
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  • Pool details: 9:00 AM to 11:00 PM, it is an indoor heated pool
  • Three Star Rural property
More Photos Pool image of Holiday Inn Express Hotel & Suites Chester by IHG
From$130 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
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Fairfield Inn & Suites by Marriott Goshen Middletown 20 Hatfield Lane, Goshen, NY 10924
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~4.69 miles northwest of Chester
  • Includes a pool: Outdoor seasonal pool open from Memorial day to Labor day from 9:00 AM to 9:00 PM.
  • Affordable Suburban property
More Photos Pool image of Fairfield Inn & Suites by Marriott Goshen Middletown
From$90 total
Very Good 4.0 /5 Review Score Call BookMore Details
Comfort Suites 100 Estrada Rd., Woodbury, NY 10917
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~8.10 miles east of Chester
  • Pool in hotel: Indoor heated pool
  • 3 star Suburban property
More Photos hotel room
From$174 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Courtyard by Marriott in Middletown 24 Crystal Run Crossing, Middletown, NY 10941
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~8.15 miles northwest of Chester
  • Pool in hotel: Indoor Pool open until 11:00pm
  • 3-star Suburban hotel
More Photos Swimming pool at Courtyard by Marriott
From$126 total
Very Good 4.5 /5 Reviews Call BookMore Details
Hampton Inn Middletown Ny 20 Crystal Run Crossing, Middletown, NY 10941
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~8.18 miles northwest of Chester
  • Pool in hotel: Seasonal; Memorial Day - Labor Day
  • Cheap Suburban hotel
More Photos Photo of Hampton Inn Middletown Ny Pool
From$72 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen in Middletown 20 Med Parc Rd., Middletown, NY 10940
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~8.38 miles northwest of Chester
  • Pool in hotel: Indoor heated pool open from 5:00am-11:00pm.
  • Mid-scale Downtown property
More Photos Swimming pool at Holiday Inn Express & Suites Middletown Goshen
From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Home2 Suites by Hilton Middletown : 600 Route 211 East 600 Route 211 East, Middletown, NY 10941
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~9.17 miles northwest of Chester
  • Includes a pool: Indoor Saline Pool open all year round. 5:30am-10pm
  • Mid-scale Suburban hotel
More Photos Swimming pool at Home2 Suites by Hilton Middletown
From$130 total
Very Good 4.0 /5 Reviews Call BookMore Details
Sleep Inn & Suites Middletown Goshen 3491 Route 6, Middletown, NY 10940
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~9.60 miles west of Chester
  • Includes a pool: Our heated salt water pool was chosen due to its many health benefits. The salt water pool is located indoors, and operates from 7:00 am to 10:00 pm. The depth is 4 foot 11 inches.
  • Cheap Highway property
More Photos Pool image of Sleep Inn & Suites Middletown Goshen
From$106 total
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Homewood Suites Stewart Airport 180 Breunig Rd., New Windsor, NY 12553
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~12.66 miles northeast of Chester
  • Has swimming pool: Open daily 8:00am-10:00pm, Hotel guests can enjoy our indoor, heated pool and hot tub.
  • Four-star Rural property
More Photos Swimming pool at Homewood Suites Stewart Airport
From$94 total
Average 3.0 /5 Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport in Newburgh 4 Governor Dr., Newburgh, NY 12550
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~13.84 miles northeast of Chester
  • We have a pool
  • Three Star Rural property
More Photos Swimming pool at Courtyard by Marriott Newburgh Stewart Airport
From$136 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport : 1 Crossroads Court 1 Crossroads Court, Newburgh, NY 12550
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~14.18 miles northeast of Chester
  • Pool in hotel: Indoors from 6am to 10pm
  • Midscale Suburban property
More Photos Swimming pool at Hampton Inn & Suites Newburgh Stewart Airport
From$166 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Overlook Lodge at Bear Mountain 55 Hessian Dr., Bear Mountain, NY 10911
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~14.25 miles east of Chester
  • Includes a pool: outdoor pool only open Memorial day to Labor day and open to the public
  • Midscale Mountain property
More Photos Photo of Overlook Lodge at Bear Mountain Pool
From$48 total
Average 3.5 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill in Peekskill 2 John Walsh Blvd., Peekskill, NY 10566
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~17.74 miles east of Chester
  • Pool available: heated indoor pool open from 8am-10pm daily, no lifeguard on duty
  • Three Star Riverfront hotel
More Photos Photo of Holiday Inn Express & Suites Peekskill Pool
From$116 total
Average 3.0 /5 Guest Reviews Call BookMore Details
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Inn on the Hudson 634 Main St., Peekskill, NY 10566
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~18.02 miles east of Chester
  • Pool in hotel: Pool is permanently closes
  • 2-star Riverfront hotel
More Photos Pool image of Inn on the Hudson
From$130 total
Average 3.0 /5 Reviews Call BookMore Details
Courtyard by Marriorr 140 Nj 17, Mahwah, NJ 07430
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~18.42 miles south of Chester
  • Pool in hotel: Indoor Heated Pool with outdoor terrace
  • Mid-scale Suburban property
More Photos Pool image of Courtyard by Marriorr
From$142 total
Average 3.0 /5 Guest Reviews Call BookMore Details
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Fairfield Inn & Suites Mahwah - Mahwah 225 Ramapo Valley Rd., Mahwah, NJ 07430
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~18.61 miles south of Chester
  • Has swimming pool: Indoor Pool is open 6AM-11PM Daily.
  • Midscale Suburban property
More Photos Photo of Fairfield Inn & Suites Mahwah Pool
From$106 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Doubletree by Hilton Mahwah - Mahwah 180 Route 17 South, Mahwah, NJ 07430
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~18.66 miles south of Chester
  • Pool available: Your friends and family would be ecstatic at the ability to utilize our heated indoor pool, which is open for use for all of our hotel guests.
  • 3 star Suburban hotel
More Photos Pool image of Doubletree by Hilton Mahwah
From$126 total
Average 3.0 /5 Reviews Call BookMore Details
The Roundhouse in Beacon 2 East Main St., Beacon, NY 12508
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~18.67 miles northeast of Chester
  • Our hotel comes with a pool
  • Three Star hotel
More Photos Pool image of The Roundhouse
From$108 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Doubletree : 180 Nj 17 180 Nj 17, Mahwah, NJ 07430
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~18.68 miles south of Chester
  • Includes a pool: Currently being renovated
  • Economical hotel
More Photos Photo of Doubletree Pool
From$72 total
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn Mahwah Newly Renovated 290 Route 17 Corporate Dr., Mahwah, NJ 07430
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~19.24 miles south of Chester
  • Pool details: Indoor Pool : 8am - 10pm
  • Low Cost Suburban hotel
More Photos Swimming pool at Hampton Inn Mahwah Newly Renovated
From$118 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Mahwah - Mahwah 375 Corporate Dr., Mahwah, NJ 07430
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~19.35 miles south of Chester
  • Has swimming pool
  • Midscale hotel
More Photos Pool image of Homewood Suites by Hilton Mahwah
From$121 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Grand Cascades Lodge 1 Wild Turkey Way, Hamburg, NJ 07419
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~20.00 miles southwest of Chester
  • Pool details: The Resort has 3 pool complexes, 2 of which are indoor/outdoor and are open year round.
  • High-end Mountain property
More Photos Pool image of Grand Cascades Lodge
From$238 total
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Nanuet in Nanuet 270 West Rte 59, Nanuet, NY 10954
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~20.32 miles southeast of Chester
  • Pool details: Indoor Heated Pool & Whirlpool open daily from 5am-10pm
  • Mid-scale Suburban property
More Photos Photo of Hilton Garden Inn Nanuet Pool
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Nanuet 260 Ny 59, Nanuet, NY 10954
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~20.32 miles southeast of Chester
  • Has swimming pool: Indoor Pool - 6 AM – 10 PM
  • Mid-scale Highway hotel
More Photos Swimming pool at Hampton Inn Nanuet
From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Fishkill - Fishkill 500 a Westage Business Center Dr., Fishkill, NY 12524
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~22.43 miles northeast of Chester
  • Has swimming pool: Large indoor pool opened daily from 6am-11pm
  • Mid-scale Downtown hotel
More Photos Pool image of Residence Inn by Marriott Fishkill
From$202 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Springhill Suites by Marriott Fishkill - Fishkill 500 B Westage Business Center Dr., Fishkill, NY 12524
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~22.43 miles northeast of Chester
  • Pool details: Large indoor pool opened daily from 6am-11pm
  • Midscale Downtown hotel
More Photos Swimming pool at Springhill Suites by Marriott Fishkill
From$118 total
Excellent 5.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Fishkill - Fishkill 25 Westage Dr., Fishkill, NY 12524
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~22.51 miles northeast of Chester
  • Pool in hotel: Our 24' x 15' indoor pool is open from 9:00 AM - 10:00 PM and also includes a luxurious hot tub. The pool and hot tub are located directly next to our fitness center which is available to our guests 24 x 7 .
  • 3 star Highway hotel
More Photos Swimming pool at Hilton Garden Inn Fishkill
From$118 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hyatt House Fishkill / Poughkeepsie 100 Westage Business Center Dr., Fishkill, NY 12524
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~22.54 miles northeast of Chester
  • Has swimming pool: The HYATT house has an indoor pool, whirlpool and fitness center and is open to guests between 8:00am and 10:00pm
  • 3-star Suburban property
More Photos Pool image of Hyatt House Fishkill / Poughkeepsie
From$126 total
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn 544 Route 9, Fishkill, NY 12524
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~22.65 miles northeast of Chester
  • Pool in hotel: Pool is open from 6am-10pm. Recently renovated!
  • Affordable Suburban property
More Photos Pool image of Hampton Inn
From$94 total
Very Good 4.5 /5 Read Reviews Call BookMore Details
Best Western Fishkill Inn & Suites 14 Schuyler Blvd., Fishkill, NY 12524
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~22.68 miles northeast of Chester
  • Pool available: Seasonal Outdoor Pool, located in Patio Area. Open Memorial day Through Labor day.
  • Three Star Suburban hotel
More Photos Pool image of Best Western Fishkill Inn & Suites
From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG - Fishkill 21 Schuyler Blvd., Fishkill, NY 12524
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~22.76 miles northeast of Chester
  • Pool available: Our indoor pool and spa, which is under a solarium to let natural sunlight in, is open everyday from 10:00 AM to 11:00 PM.
  • Affordable Suburban hotel
More Photos Pool image of Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
From$76 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Doubletree by Hilton Hotel Nanuet : 425 East Route 59 425 East Route 59, Nanuet, NY 10954
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~22.96 miles southeast of Chester
  • Pool available: Indoor Heated pool with whirlpool. 9am-9pm
  • Mid-scale Suburban hotel
More Photos Photo of Doubletree by Hilton Hotel Nanuet Pool
From$130 total
Very Good 4.0 /5 Review Score Call BookMore Details
Courtyard by Marriott Montvale in Montvale 100 Chestnut Ridge Rd., Montvale, NJ 07645
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~23.10 miles southeast of Chester
  • Has swimming pool: We have an large Outdoor Pool along side our beautiful patio.
  • Affordable Suburban property
More Photos Swimming pool at Courtyard by Marriott Montvale
From$130 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Residence Inn by Marriott Saddle River in Saddle River 7 Boroline Rd., Saddle River, NJ 07458
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~23.34 miles south of Chester
  • Includes a pool: Seasonal Outdoor Pool /open Memorial Day - Labor Day from 9AM - 9PM. (Weather restrictions may apply)
  • Mid-scale Suburban property
More Photos Pool image of Residence Inn by Marriott Saddle River
From$154 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Haskell - Wayne Area by IHG 303 Union Ave., Haskell, NJ 07420
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~23.38 miles south of Chester
  • Includes a pool: Indoor Heater pool, Hours of operation: 6am -10:30pm
  • Mid-scale Suburban hotel
More Photos Swimming pool at Holiday Inn Express Haskell - Wayne Area by IHG
From$90 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Hunt's Landing Hotel Matamoras/Milford - Matamoras 120 Routes 6 & 209, Matamoras, PA 18336
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~23.41 miles west of Chester
  • Pool details: This hotel offers an indoor, heated pool; operation hours: 6:00 am-10pm.
  • 2 star Highway hotel
More Photos Pool image of Best Western Hunt's Landing Hotel Matamoras/Milford
From$82 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Marriott Park Ridge : 300 Brae Blvd. 300 Brae Blvd., Park Ridge, NJ 07656
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~24.00 miles southeast of Chester
  • Pool in hotel: Indoor Pool Mon-Sun: 8:00 AM-10:00 PM Outdoor Pool (Seasonal) Mon-Sun: 8:00 AM-10:00 PM Outdoor Towels provided Heated Whirlpool Adjacent to the indoor pool Fitness Center Complimentary Open 7 days a week, 24 hours a day
  • Four-star hotel
More Photos Photo of Marriott Park Ridge Pool
From$130 total
Very Good 4.0 /5 Review Score Call BookMore Details
Hilton Pearl River in Pearl River 500 Veterans Memorial Dr., Pearl River, NY 10965
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~25.25 miles southeast of Chester
  • Pool details: Indoor
  • Midscale Suburban property
More Photos Pool image of Hilton Pearl River
From$190 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hyatt Place Poughkeepsie - Poughkeepsie 2165 South Rd., Poughkeepsie, NY 12601
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~26.34 miles northeast of Chester
  • Pool in hotel: Swim laps in our indoor pool or elect to relax on a lounger poolside from 8AM - 10PM
  • Three Star Highway hotel
More Photos Pool image of Hyatt Place Poughkeepsie
From$142 total
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Poughkeepsie 2361 South Rd., Poughkeepsie, NY 12601
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~26.76 miles northeast of Chester
  • Pool details: Indoor Pool - 8am - 10pm
  • Mid-scale Suburban property
More Photos Photo of Hampton Inn & Suites Poughkeepsie Pool
From$114 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Wayne in Wayne 15 Nevins Rd., Wayne, NJ 07470
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~26.91 miles south of Chester
  • Pool available: Dive into relaxation in our indoor swimming pool. After an intense workout, soothe your sore muscles in the whirlpool. The pool area is open daily 8:00 AM until 11:00 PM. Stay active with our state-of-the-art fitness center, open 24 hours a day. Choose from a variety of different cardio machines, free weights, medicine balls and more.
  • 3 star Suburban property
More Photos Swimming pool at Hilton Garden Inn Wayne
From$123 total
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Days Inn by Wyndham Wayne - Wayne 1850 Nj 23, Wayne, NJ 07470
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~28.14 miles south of Chester
  • Has swimming pool: we have out door pool
  • Two-star Suburban property
More Photos Pool image of Days Inn by Wyndham Wayne
From$72 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Americas Best Value Inn New Paltz : 7 Terwilliger Lane 7 Terwilliger Lane, New Paltz, NY 12561
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~28.54 miles north of Chester
  • Has swimming pool: Outdoor Pool
  • 2-star property
More Photos Swimming pool at Americas Best Value Inn New Paltz
From$60 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Sleepy Hollow Hotel a Dolce by Wyndham - Tarrytown 455 South Broadway, Tarrytown, NY 10591
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~29.13 miles southeast of Chester
  • Has swimming pool: 6am - 11pm 800 sq. ft - 3-5 feet Indoor heated pool
  • Expensive Suburban property
More Photos Photo of Sleepy Hollow Hotel a Dolce by Wyndham Pool
From$142 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hotel Mtk Mount Kisco 1 Holiday Inn Dr., Mount Kisco, NY 10549
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~29.60 miles east of Chester
  • Pool available: Seasonal outdoor pool - open Memorial Day to Labor Day
  • Mid-scale Suburban hotel
More Photos Swimming pool at Hotel Mtk Mount Kisco
From$154 total
Average 3.0 /5 Recent Reviews Call BookMore Details
SpringHill Suites by Marriott Tarrytown Westchester County 480 White Plains Rd., Tarrytown, NY 10591
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~29.76 miles southeast of Chester
  • Pool details: Indoor Pool, Open 6AM to 10PM
  • 3 star Suburban hotel
More Photos Photo of SpringHill Suites by Marriott Tarrytown Westchester County Pool
From$90 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Tarrytown House Estate : 49 East Sunnyside Lane 49 East Sunnyside Lane, Tarrytown, NY 10591
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~29.84 miles southeast of Chester
  • Pool in hotel: Both indoor and outdoor pool, gym, sauna
  • 3-star Suburban hotel
More Photos Swimming pool at Tarrytown House Estate
From$106 total
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn Monticello - Monticello 29 Golden Ridge Rd., Monticello, NY 12701
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~30.03 miles northwest of Chester
  • Has swimming pool: Our indoor heated pool is open from 8 am - 10 pm
  • Three Star Rural hotel
More Photos hotel room
From$96 total
Average 3.0 /5 Review Score Call BookMore Details
Resorts World Catskills Casino 888 a Resorts World Dr., Monticello, NY 12701
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~30.13 miles northwest of Chester
  • Pool available: Dive into the extraordinary. Guests of the hotel enjoy access to our indoor pool for year round relaxation. Recline the day away in the comfortable chaise lounges, daybeds, or cabanas all while soaking the simply gorgeous outside views that surround our outside pool deck. Pool Hours: 7AM- 10PM
  • Expensive property
More Photos Photo of Resorts World Catskills Casino Pool
From$178 total
Average 3.5 /5 Latest Reviews Call BookMore Details
Courtyard by Marriott Paramus 320 North Route 17, Paramus, NJ 07652
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~30.13 miles south of Chester
  • Includes a swimming pool
  • Midscale Suburban property
More Photos Pool image of Courtyard by Marriott Paramus
From$96 total
Very Good 4.0 /5 Review Score Call BookMore Details

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