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.
Planning group travel? Get Chester NY Group Hotel Rates

Chester Hotels with Outdoor or Indoor Pools

Holiday Inn Express & Suites
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
2 Bryle Pl, Chester, NY 10918 +1-888-389-4121
  • Pool available: 9:00 AM to 11:00 PM, it is an indoor heated pool
  • 3 star Rural hotel
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From$109
Very good 4.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Goshen Middletown : 20 Hatfield Lane
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
20 Hatfield Lane, Goshen, NY 10924 +1-888-675-2083 ~4.69 miles northwest of Chester
  • Pool available: Outdoor seasonal pool open from Memorial day to Labor day from 9:00 AM to 9:00 PM.
  • 3 star Suburban property
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From$75
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Comfort Suites - Woodbury
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
100 Estrada Rd., Woodbury, NY 10917 +1-800-716-8490 ~8.10 miles east of Chester
  • Pool available: Indoor heated pool
  • 3 star Suburban property
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From$145
Average 3.0 /5 Review Score Call BookMore Details
Courtyard by Marriott in Middletown
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
24 Crystal Run Crossing, Middletown, NY 10941 +1-800-805-5223 ~8.15 miles northwest of Chester
  • Includes a pool: Indoor Pool open til 11pm
  • 3-star Suburban hotel
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From$105
Very good 4.5 /5 Reviews Call BookMore Details
Hampton Inn Middletown Ny - Middletown
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
20 Crystal Run Crossing, Middletown, NY 10941 +1-888-965-1860 ~8.18 miles northwest of Chester
  • Has swimming pool: Seasonal; Memorial Day - Labor Day
  • Low Cost Suburban property
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From$60
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen : 20 Med Parc Rd.
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
20 Med Parc Rd., Middletown, NY 10940 +1-888-788-5576 ~8.38 miles northwest of Chester
  • Pool details: Indoor heated pool open from 5:00am-11:00pm.
  • Three Star Downtown property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Sleep Inn & Suites Middletown Goshen
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
3491 Route 6, Middletown, NY 10940 +1-888-897-9207 ~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.
  • Economy Highway hotel
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From$89
Very good 4.5 /5 Guest Reviews Call BookMore Details
Homewood Suites by Hilton Newburgh Stewart Airport in New Windsor
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
180 Breunig Rd., New Windsor, NY 12553 +1-888-311-4278 ~12.66 miles northeast of Chester
  • Pool in hotel: Open daily 8:00am-10:00pm, Hotel guests can enjoy our indoor, heated pool and hot tub.
  • High end Rural hotel
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From$79
Average 3.0 /5 Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
4 Governor Dr., Newburgh, NY 12550 +1-888-469-4795 ~13.84 miles northeast of Chester
  • Has swimming pool
  • Three Star Rural property
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From$114
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Newburgh Stewart Airport : 1 Crossroads Court
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1 Crossroads Court, Newburgh, NY 12550 +1-888-734-9421 ~14.18 miles northeast of Chester
  • Has swimming pool: Indoors from 6am to 10pm
  • Mid-scale Suburban hotel
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From$139
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Overlook Lodge at Bear Mountain : 55 Hessian Dr.
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
55 Hessian Dr., Bear Mountain, NY 10911 +1-888-841-5292 ~14.25 miles east of Chester
  • Pool available: outdoor pool only open Memorial day to Labor day and open to the public
  • Affordable Mountain property
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From$40
Average 3.5 /5 Reviews Call BookMore Details
Bear Mountain Inn in Bear Mountain
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
3020 Seven Lakes Dr., Bear Mountain, NY 10911 +1-888-455-5160 ~14.43 miles east of Chester
  • Pool available: outdoor pool only open Memorial day to Labor day and open to the public
  • 3-star Mountain hotel
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From$149
Very good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill in Peekskill
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
2 John Walsh Blvd., Peekskill, NY 10566 +1-888-965-8297 ~17.74 miles east of Chester
  • Has swimming pool: heated indoor pool open from 8am-10pm daily, no lifeguard on duty
  • Affordable Riverfront property
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From$97
Average 3.0 /5 Reviews Call BookMore Details
Inn on the Hudson
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
634 Main St., Peekskill, NY 10566 +1-888-906-6358 ~18.02 miles east of Chester
  • Includes a pool: Pool is permanently closes
  • Two star Riverfront property
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From$109
Average 3.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Mahwah in Mahwah
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
140 Nj 17, Mahwah, NJ 07430 +1-888-749-6785 ~18.42 miles south of Chester
  • Pool details: Indoor Heated Pool.
  • Midscale Suburban property
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Fairfield Inn & Suites Mahwah in Mahwah
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
225 Ramapo Valley Rd., Mahwah, NJ 07430 +1-888-878-9982 ~18.61 miles south of Chester
  • Pool in hotel: Indoor Pool is open 6AM-11PM Daily.
  • Three Star Suburban hotel
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From$89
Average 3.0 /5 Latest Reviews Call BookMore Details
Doubletree by Hilton Mahwah
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
180 Route 17 South, Mahwah, NJ 07430 +1-888-389-4485 ~18.66 miles south of Chester
  • Pool in hotel: 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.
  • Three Star Suburban hotel
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From$105
Average 3.0 /5 Latest Reviews Call BookMore Details
Doubletree - Mahwah
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
180 Nj 17, Mahwah, NJ 07430 +1-888-389-4121 ~18.68 miles south of Chester
  • Includes a pool: Currently being renovated
  • Economical hotel
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From$60
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn Mahwah
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
290 Route 17 Corporate Dr., Mahwah, NJ 07430 +1-888-675-2083 ~19.24 miles south of Chester
  • Pool available: Indoor Pool : 8am - 10pm
  • Economy property
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From$99
Average 3.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Nanuet
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
270 West Rte 59, Nanuet, NY 10954 +1-800-716-8490 ~20.32 miles southeast of Chester
  • Pool details: Indoor Heated Pool & Whirlpool open daily from 5am-10pm
  • Mid-scale Suburban hotel
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Nanuet - Nanuet
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
260 West Rte 59, Nanuet, NY 10954 +1-800-805-5223 ~20.32 miles southeast of Chester
  • Pool details: Indoor Pool - 6 AM – 10 PM
  • 3 star Highway hotel
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Days Inn by Wyndham Nanuet / Spring Valley in Nanuet
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
367 West Route 59, Nanuet, NY 10954 +1-888-965-1860 ~21.39 miles southeast of Chester
  • Pool details: The Days Inn of Nanuet offers an outdoor heated pool from the hours of 9AM to 8PM.
  • Inexpensive Highway hotel
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From$70
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Poughkeepsie / Fishkill
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
25 Westage Dr., Fishkill, NY 12524 +1-888-788-5576 ~22.51 miles northeast of Chester
  • Includes a pool: 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 .
  • Three Star Highway hotel
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From$99
Very good 4.0 /5 Reviews Call BookMore Details
HYATT house Fishkill/Poughkeepsie - Fishkill
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
100 Westage Business Center Dr., Fishkill, NY 12524 +1-888-897-9207 ~22.54 miles northeast of Chester
  • Pool details: 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 hotel
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From$105
Very good 4.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Fishkill in Fishkill
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
17 Westage Dr., Fishkill, NY 12524 +1-888-311-4278 ~22.59 miles northeast of Chester
  • Includes a pool: 7am-10pm
  • 3 star Suburban property
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From$80
Average 3.0 /5 Review Score Call BookMore Details
Best Western Fishkill Inn & Suites in Fishkill
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
14 Schuyler Blvd., Fishkill, NY 12524 +1-888-469-4795 ~22.68 miles northeast of Chester
  • Has swimming pool: Seasonal Outdoor Pool, located in Patio Area. Open Memorial day Through Labor day.
  • Three Star Suburban hotel
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express in Fishkill
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
21 Schuyler Blvd., Fishkill, NY 12524 +1-888-734-9421 ~22.76 miles northeast of Chester
  • Pool details: 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
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From$64
Very good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Fishkill
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
544 Us 9, Fishkill, NY 12524 +1-888-841-5292 ~22.77 miles northeast of Chester
  • Pool available: Pool is open from 6am-10pm. Recently renovated!
  • Three Star Suburban hotel
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Hunt's Landing Hotel Matamoras/Milford
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
120 Routes 6 & 209, Matamoras, PA 18336 +1-888-455-5160 ~23.41 miles west of Chester
  • Pool details: This hotel offers an indoor, heated pool; operation hours: 6:00 am-10pm.
  • Inexpensive Highway property
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From$69
Very good 4.0 /5 Reviews Call BookMore Details
Hotel Nyack, a JdV by Hyatt Hotel
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
400 High Ave., Nyack, NY 10960 +1-888-965-8297 ~24.98 miles southeast of Chester
  • Pool in hotel: Seasonal Outdoor Pool/ Hot Tub/ Deck 8AM-9PM
  • Four star Suburban hotel
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From$88
Average 3.0 /5 Read Reviews Call BookMore Details
Hyatt Place Poughkeepsie / Hudson Valley in Poughkeepsie
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
2165 South Rd., Poughkeepsie, NY 12601 +1-888-906-6358 ~26.34 miles northeast of Chester
  • Pool available: Swim laps in our indoor pool or elect to relax on a lounger poolside from 8AM - 10PM
  • Mid-scale Highway property
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From$119
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Poughkeepsie - Poughkeepsie
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
2361 South Rd., Poughkeepsie, NY 12601 +1-888-749-6785 ~26.76 miles northeast of Chester
  • Has swimming pool: Indoor Pool - 8am - 10pm
  • 3 star Suburban property
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From$95
Average 3.0 /5 Recent Reviews Call BookMore Details
Days Inn by Wyndham Wayne
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
1850 Nj 23, Wayne, NJ 07470 +1-888-878-9982 ~28.14 miles south of Chester
  • Includes a pool: we have out door pool
  • Economy Suburban property
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From$60
Average 3.0 /5 Review Score Call BookMore Details
Americas Best Value Inn New Paltz in New Paltz
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
7 Terwilliger Lane, New Paltz, NY 12561 +1-888-389-4485 ~28.54 miles north of Chester
  • Pool available: Outdoor Pool
  • Inexpensive hotel
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From$50
Very good 4.0 /5 Read Reviews Call BookMore Details
Hotel Mtk Mount Kisco
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
1 Pat Reilly Way, Mount Kisco, NY 10549 +1-888-389-4121 ~29.51 miles east of Chester
  • Has swimming pool: Seasonal outdoor pool - open Memorial Day to Labor Day
  • Affordable Suburban hotel
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From$129
Very good 4.0 /5 Reviews Call BookMore Details
Tarrytown Springhill Suites by Marriott
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
480 White Plains Rd., Tarrytown, NY 10591 +1-888-675-2083 ~29.76 miles southeast of Chester
  • Pool in hotel: Indoor Pool, Open 6AM to 10PM
  • Midscale Suburban hotel
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From$75
Average 3.0 /5 Review Score Call BookMore Details
Tarrytown House Estate
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
49 East Sunnyside Lane, Tarrytown, NY 10591 +1-800-716-8490 ~29.84 miles southeast of Chester
  • Pool in hotel: Both indoor and outdoor pool, gym, sauna
  • 3-star Suburban hotel
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From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Sheraton Tarrytown Hotel
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
600 White Plains Rd., Tarrytown, NY 10591 +1-800-805-5223 ~30.13 miles southeast of Chester
  • Pool in hotel: 6am- 10pm, indoor pool and hot tub
  • Three Star Suburban hotel
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From$75
Very good 4.0 /5 Hotel Reviews Call BookMore Details
The Kartrite Resort Indoor Waterpark
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
555 Resorts World Dr., Monticello, NY 12701 +1-888-965-1860 ~30.17 miles northwest of Chester
  • Pool available: 11am-7pm
  • 3 star Mountain property
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From$90
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western Monticello : 16 Raceway Rd.
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
16 Raceway Rd., Monticello, NY 12701 +1-888-788-5576 ~31.03 miles northwest of Chester
  • Includes a pool: Indoor- 8:00 AM to 8:00 PM
  • Midscale Downtown property
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From$108
Average 3.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Westchester Dobbs Ferry
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
201 Ogden Ave., Dobbs Ferry, NY 10522 +1-888-897-9207 ~31.84 miles southeast of Chester
  • Pool available: Spacious Saltwater Heated pool will be open daily.
  • 3 star Suburban hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Doubletree by Hilton Fairfield Hotel & Suites - Fairfield
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
690 Us 46, Fairfield, NJ 07004 +1-888-311-4278 ~32.08 miles south of Chester
  • Pool available: Indoor Swimming pool open from 6:am - 10:pm daily
  • Midscale Suburban hotel
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Rockaway
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
14 Green Pond Rd., Rockaway, NJ 07866 +1-888-469-4795 ~32.98 miles southwest of Chester
  • Includes a pool: Indoor pool
  • Three Star Highway property
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Best Western Plus Fairfield Executive Inn
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
216 Route 46 East #234, Fairfield, NJ 07004 +1-888-734-9421 ~33.21 miles south of Chester
  • Includes a swimming pool
  • 2-star property
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From$95
Very good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Denville / Rockaway / Parsippany : 350 Morris Ave.
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
350 Morris Ave., Denville, NJ 07834 +1-888-841-5292 ~33.21 miles south of Chester
  • Pool details: Indoor Heated Pool Hours: 6 am to 11 pm, subject to change.
  • Mid-scale Highway property
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From$92
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Yonkers - Yonkers
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
160 Corporate Blvd., Yonkers, NY 10701 +1-888-455-5160 ~33.33 miles southeast of Chester
  • Pool details: Indoor pool
  • 3 star Suburban hotel
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Sonesta White Plains Downtown - White Plains
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
66 Hale Ave., White Plains, NY 10601 +1-888-965-8297 ~34.49 miles southeast of Chester
  • Pool in hotel: Whether you're looking for a morning boost or an evening unwind, our indoor heated pool is the go-to place. Pool hours are: Monday - Thursday: 3 pm - 7 pm Friday - Saturday: 8 am - 8 pm Sunday: 8 am - 2 pm
  • High-end Downtown property
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From$125
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Hotel & Suites Parsippany Fairfield An Ihg Hotel : 707 Us Highway 46 East
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
707 Us Highway 46 East, Parsippany, NJ 07054 +1-888-906-6358 ~34.50 miles south of Chester
  • Includes a pool: Seasonal Pool open from memorial day weekend to labor day weekend every day from 10am to 8pm
  • Midscale Suburban hotel
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From$89
Very good 4.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Dover Rockaway
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
2 Commerce Center Dr., Dover, NJ 07801 +1-888-749-6785 ~34.69 miles southwest of Chester
  • Pool available: Indoor pool hours are 9am-10pm Pool is heated.
  • 3 star Suburban property
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From$99
Very good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Parsippany Troy Hills
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
61 Interpace Pkwy., Parsippany-Troy Hills, NJ 07054 +1-888-878-9982 ~34.81 miles south of Chester
  • Pool available: Indoor pool Hours are 8am-10pm
  • 3-star Suburban hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
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