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 Place, Chester, NY 10918
  • Pool in hotel: Swimming pool, Pool sun loungers.
  • 3-star property
  • Hotel has an eco-friendly policy Read more
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Very Good 8.6 /10 Read Reviews Call BookMore Details
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LEGOLAND Hotel NEW York 1 LEGOLAND BLVD, Goshen, NY 10924 ~2.96 miles northwest of Chester
  • Pool in hotel: Pool umbrellas, Wheelchair-accessible pool, Pool toys, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May 22 to September 07.
  • Affordable property
  • 250 rooms in property
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Very Good 8.0 /10 Read Reviews Call BookMore Details
Glenmere Mansion 634 Pine Hill Road, Chester, NY 10918
  • Our hotel comes with a pool
  • Low Cost property
  • Check-in: 3:00 PM
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Fairfield Inn & Suites by Marriott Goshen Middletown 20 Hatfield Ln, Goshen, NY 10924 ~4.71 miles northwest of Chester
  • Pool available: Swimming pool, Outdoor seasonal pool. The seasonal pool will be open from May to August.
  • Affordable hotel
  • Check in: 3:00 PM - 6:00 AM
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Excellent 9.0 /10 Reviews Call BookMore Details
Hampton Inn Harriman Woodbury 60 Centre Dr, Central Valley, NY 10917 ~7.63 miles east of Chester
  • Pool available: Pool hoist on site. Pool access available from 6:00 AM to midnight.
  • Mid-scale hotel
  • Hotel has 136 rooms
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Excellent 9.1 /10 Hotel Reviews Call BookMore Details
Comfort Suites Central Valley - Woodbury 100 Estrada Road, Central Valley, NY 10917 ~8.10 miles east of Chester
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool.
  • Midscale property
  • Free breakfast available
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Very Good 8.4 /10 Reviews Call BookMore Details
Hampton Inn by Hilton Middletown 20 Crystal Run Crossing, Middletown, NY 10941 ~8.15 miles northwest of Chester
  • Has swimming pool: Outdoor seasonal pool. The seasonal pool will be open from May 30 to September 05. Pool access available from 8:00 AM to 10:00 PM.
  • Midscale property
  • Check-in: 3:00 PM - midnight
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Very Good 8.4 /10 Read Reviews Call BookMore Details
Courtyard by Marriott Middletown Goshen 24 Crystal Run Xing, Middletown, NY 10941 ~8.17 miles northwest of Chester
  • Pool available: Pool hoist on site, Wheelchair-accessible pool.
  • Affordable property
  • 4 floors in property
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Very Good 8.4 /10 Guest Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown - Goshen by IHG 20 MED PARC ROAD, Middletown, NY 10940 ~8.40 miles northwest of Chester
  • Pool details: Pool hoist on site, Wheelchair-accessible pool, Pool sun loungers.
  • Mid-scale property
  • Comp. Breakfast
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Very Good 8.8 /10 Latest Reviews Call BookMore Details
Days Inn by Wyndham Middletown 4939 Route 17 M, New Hampton, NY 10958 ~8.46 miles west of Chester
  • Pool details: Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from June to August. Pool access available from 1 PM to 8 PM.
  • Inexpensive Motel hotel
  • Hotel has 41 rooms
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Average 6.4 /10 Recent Reviews Call BookMore Details
Candlewood Suites Middletown Goshen by IHG 21 Med Parc Road, Middletown, NY 10940 ~8.54 miles northwest of Chester
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 6:00 AM to 10:00 PM.
  • Midscale property
  • Pets are Welcome
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Excellent 9.4 /10 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Middletown 600 Route 211 East, Middletown, NY 10941 ~9.18 miles northwest of Chester
  • Pool available: Wheelchair-accessible pool.
  • Mid-scale hotel
  • Check-in time: 3:00 PM - 12:30 AM
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Excellent 9.0 /10 Guest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Middletown-Goshen 551 Route 211 E, Middletown, NY 10941 ~9.42 miles northwest of Chester
  • Pool in hotel: Pool access ramp on site, Wheelchair-accessible pool. Pool access available from 9:00 AM to 9:00 PM.
  • 3 star hotel
  • Pets/Animals Allowed
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Excellent 9.4 /10 Recent Reviews Call BookMore Details
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Residence Inn by Marriott Middletown Goshen 57 TOWER DRIVE, Middletown, NY 10941 ~9.46 miles northwest of Chester
  • Pool in hotel: Wheelchair-accessible pool. Pool access available from 7:00 AM to 10:00 PM.
  • Midscale hotel
  • Hotel has 125 suites
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Excellent 9.4 /10 Review Score Call BookMore Details
Sleep Inn & Suites Middletown - Goshen 3491 Route 6, Middletown, NY 10940 ~9.62 miles west of Chester
  • Has swimming pool: Pool access available from 7:00 AM to 10:00 PM.
  • Mid-scale hotel
  • Hotel has 108 rooms
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Very Good 8.8 /10 Hotel Reviews Call BookMore Details
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Holiday Inn Express & Suites Montgomery by IHG 2105 Route 208, Montgomery, NY 12549 ~11.43 miles north of Chester
  • Pool in hotel
  • 3-star hotel
  • 81 sleeping rooms in hotel
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Very Good 8.6 /10 Reviews Call BookMore Details
Homewood Suites Stewart Airport 180 Breunig Rd, New Windsor, NY 12553 ~12.56 miles northeast of Chester
  • Pool in hotel
  • 3-star hotel
  • 125 rooms in hotel
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Excellent 9.2 /10 Latest Reviews Call BookMore Details
Red Roof Inn & Suites Newburgh – Stewart Airport / West Point 915 Union Ave, New Windsor, NY 12553 ~13.61 miles northeast of Chester
  • Pool available: Wheelchair-accessible pool. Pool access available from 10:00 AM to 9:00 PM.
  • Cheap hotel
  • Fitness + Health Center
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Very Good 8.4 /10 Recent Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport 4 Governor Dr, Newburgh, NY 12550 ~13.91 miles northeast of Chester
  • Pool details: Pool access ramp on site, Pool hoist on site, Wheelchair-accessible pool, Pool sun loungers. Pool access available from 6 AM to 11 PM.
  • Midscale property
  • Check in time: 3:00 PM - 6:00 AM
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Very Good 8.2 /10 Reviews Call BookMore Details
The Crossroads Hotel Newburgh 5 Lakeside Rd, Newburgh, NY 12550 ~14.07 miles northeast of Chester
  • Pool available: Wheelchair-accessible pool.
  • Midscale property
  • Fitness center on property
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Average 7.2 /10 Reviews Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport 1 Crossroads Ct, Newburgh, NY 12550 ~14.23 miles northeast of Chester
  • Pool in hotel: Wheelchair-accessible pool. Pool access available from 6:00 AM to 10:00 PM.
  • Affordable hotel
  • 5 floors in hotel
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Excellent 9.2 /10 Review Score Call BookMore Details
Overlook Lodge at Bear Mountain 55 Hessian Drive, Bear Mountain, NY 10911 ~14.44 miles east of Chester
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from June to September.
  • Three Star property
  • Free breakfast available
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Very Good 8.4 /10 Hotel Reviews Call BookMore Details
Ramada by Wyndham Newburgh / West Point 1289 Route 300, Newburgh, NY 12550 ~14.63 miles northeast of Chester
  • Has a pool!
  • Cheap property
  • Check in: 3:00 PM - 7:00 AM
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Poor 4.8 /10 Hotel Reviews Call BookMore Details
THE RANCH HUDSON VALLEY 150 SISTER SERVANTS LANE, Sloatsburg, New York 10974 ~14.83 miles south of Chester
  • Pool details: Pool access available from 6:00 AM to 9:00 PM.
  • 3 star property
  • Pets are OK
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Holiday Inn Express West Point by IHG 1106 Route 9 W, Fort Montgomery, NY 10922 ~15.02 miles east of Chester
  • Includes a swimming pool
  • Affordable property
  • 16 suites in hotel
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Excellent 9.2 /10 Guest Reviews Call BookMore Details
Mountain Creek 200 Route 94, Vernon, NJ 07462 ~16.86 miles southwest of Chester
  • Has swimming pool: Pool umbrellas, Billiards or pool table, Pool sun loungers, Fence around pool. Pool access available from 10:00 AM to 10:00 PM.
  • Three Star hotel
  • 4 floors in hotel
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Excellent 9.1 /10 Latest Reviews Call BookMore Details
Harvest Inn 95 Boniface Dr, Pine Bush, NY 12566 ~17.04 miles north of Chester
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from June 01 to September 03.
  • 3 star hotel
  • Check-in: 4:00 PM - anytime
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Excellent 9.4 /10 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG 2 John Walsh Boulevard, Peekskill, NY 10566 ~17.81 miles east of Chester
  • Includes a pool: Wheelchair-accessible pool.
  • Midscale property
  • Free complimentary breakfast
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Excellent 9.2 /10 Hotel Reviews Call BookMore Details
Mirbeau Inn & Spa Beacon 11 Mirbeau Lane, Beacon, NY 12508 ~18.02 miles northeast of Chester
  • Pool in hotel: Pool cabanas (surcharge).
  • Affordable property
  • Hotel has 72 rooms
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Excellent 9.4 /10 Reviews Call BookMore Details
The Abbey Inn & Spa 900 Fort Hill Rd, Peekskill, NY 10566 ~18.03 miles east of Chester
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • 4 star property
  • Access to gym on-site
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Excellent 9.2 /10 Guest Reviews Call BookMore Details
Inn on the Hudson 634 Main Street, Peekskill, NY 10566 ~18.19 miles east of Chester
  • Includes a swimming pool
  • Economy property
  • Check in time: 3:00 PM - midnight
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Courtyard by Marriott Mahwah 140 NJ 17 South, Mahwah, NJ 07430 ~18.42 miles south of Chester
  • Pool details: Wheelchair-accessible pool.
  • 3-star property
  • Hotel has an eco-friendly policy See policy
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Very Good 8.2 /10 Reviews Call BookMore Details
Fairfield Inn & Suites Mahwah 225 Ramapo Valley Road, Mahwah, NJ 07430 ~18.59 miles south of Chester
  • Pool in hotel: Wheelchair-accessible pool.
  • Three Star hotel
  • 3 floors in hotel
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Very Good 8.2 /10 Reviews Call BookMore Details
DoubleTree by Hilton Mahwah 180 Route 17 S, Mahwah, NJ 07430 ~18.65 miles south of Chester
  • Has swimming pool: Wheelchair-accessible pool.
  • High end property
  • Has environment-friendly policy Learn more
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Average 7.8 /10 Read Reviews Call BookMore Details
Days Inn by Wyndham Wurtsboro 21 Perron Dr, Wurtsboro, NY 12790 ~19.02 miles northwest of Chester
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from May to September. Pool access available from 9 AM to 9 PM.
  • Economical Motel property
  • Check-in time: 3:00 PM - anytime
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Average 7.6 /10 Latest Reviews Call BookMore Details
Hampton Inn & Suites Mahwah 290 Rt 17s, Mahwah, NJ 07430 ~19.24 miles south of Chester
  • Pool in hotel: Pool hoist on site, Wheelchair-accessible pool.
  • Mid-scale property
  • Has environment-friendly policy Read more
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Very Good 8.8 /10 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Mahwah 375 Corporate Dr, Mahwah, NJ 07430 ~19.35 miles south of Chester
  • Includes a pool: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Midscale hotel
  • Check-in: 4:00 PM - midnight
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Very Good 8.6 /10 Guest Reviews Call BookMore Details
Quality Inn Spring Valley - Nanuet 100 Spring Valley Marketplace, Spring Valley, NY 10977 ~21.34 miles southeast of Chester
  • With a pool!
  • Midscale hotel
  • Check in: 3:00 PM
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Average 6.2 /10 Review Score Call BookMore Details
Days Inn by Wyndham Nanuet / Spring Valley 367 West Route 59, Nanuet, NY 10954 ~21.43 miles southeast of Chester
  • Includes a pool
  • Economy Motel property
  • 2 floors in hotel
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Average 7.0 /10 Review Score Call BookMore Details
Element by Marriott Spring Valley 90 Spring Valley Market Place, Spring Valley, NY 10977 ~21.44 miles southeast of Chester
  • Has swimming pool: Wheelchair-accessible pool.
  • Affordable property
  • Hotel has 50 suites
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Very Good 8.8 /10 Guest Reviews Call BookMore Details
Comfort Suites Fishkill near Interstate 84 835 Route 52, Fishkill, NY 12524 ~21.48 miles northeast of Chester
  • Pool details: Pool hoist on site, Wheelchair-accessible pool.
  • Three Star property
  • Access to gym on-site
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Excellent 9.2 /10 Review Score Call BookMore Details
Hampton Inn Nanuet 260 West Route 59, Nanuet, NY 10954 ~21.61 miles southeast of Chester
  • Has swimming pool: Swimming pool, Wheelchair-accessible pool. Pool access available from 8:00 AM to 10:00 PM.
  • Three Star property
  • Check in: 3:00 PM - midnight
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Very Good 8.2 /10 Hotel Reviews Call BookMore Details
Hilton Garden Inn Nanuet 270 West Route 59, Nanuet, NY 10954 ~21.66 miles southeast of Chester
  • Pool details: Wheelchair-accessible pool.
  • 3-star hotel
  • Pets Welcome
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Average 7.8 /10 Review Score Call BookMore Details
Residence Inn by Marriott Fishkill 500 Westage Business Center Drive, Fishkill, NY 12524 ~22.35 miles northeast of Chester
  • Pool details: Wheelchair-accessible pool. Pool access available from 6 AM to 11 PM.
  • 3-star hotel
  • 3 floors in hotel
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Excellent 9.4 /10 Read Reviews Call BookMore Details
SpringHill Suites by Marriott Fishkill 500 Westage Business Center Drive, Fishkill, NY 12524 ~22.35 miles northeast of Chester
  • Pool details: Swimming pool, Wheelchair-accessible pool. Pool access available from 6 AM to 11 PM.
  • 3 star hotel
  • Free comp. breakfast
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Excellent 9.6 /10 Reviews Call BookMore Details
HYATT house Fishkill / Poughkeepsie 100 Westage Business Center Dr., Fishkill, NY 12524 ~22.53 miles northeast of Chester
  • Pool details: Pool sun loungers.
  • Mid-scale hotel
  • Check-in: 4:00 PM - anytime
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Very Good 8.8 /10 Review Score Call BookMore Details
Hilton Garden Inn Fishkill 25 Westage Road, Fishkill, NY 12524 ~22.68 miles northeast of Chester
  • Pool in hotel: Pool access available from 9:00 AM to 10:00 PM.
  • 3-star property
  • Pets are OK
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Very Good 8.6 /10 Hotel Reviews Call BookMore Details
Best Western Fishkill Inn & Suites 14 Schuyler Blvd, Fishkill, NY 12524 ~22.74 miles northeast of Chester
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from June to August.
  • Mid-scale hotel
  • 139 suites in hotel
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Very Good 8.8 /10 Reviews Call BookMore Details
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG 21 Schuyler Blvd, Fishkill, NY 12524 ~22.81 miles northeast of Chester
  • Includes a pool: Wheelchair-accessible pool.
  • 3-star property
  • Fitness / Gym is on-site
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Very Good 8.3 /10 Reviews Call BookMore Details
Hampton Inn Fishkill 544 Route 9, Fishkill, NY 12524 ~22.84 miles northeast of Chester
  • Includes a pool
  • Affordable property
  • Complimentary breakfast is offered
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Very Good 8.6 /10 Reviews Call BookMore Details

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