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 - Chester
+1-888-389-4121

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

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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 Latest Reviews Call BookMore Details
Courtyard by Marriott in Middletown
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
24 Crystal Run Crossing, Middletown, NY 10941 +1-800-716-8490 ~8.15 miles northwest of Chester
  • Includes a pool: Indoor Pool open til 11pm
  • 3-star Suburban property
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From$105
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Hampton Inn Middletown Ny
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
20 Crystal Run Crossing, Middletown, NY 10941 +1-800-805-5223 ~8.18 miles northwest of Chester
  • Pool details: Seasonal; Memorial Day - Labor Day
  • Cheap Suburban hotel
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From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Middletown Goshen
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
20 Med Parc Rd., Middletown, NY 10940 +1-888-965-1860 ~8.38 miles northwest of Chester
  • Pool available: Indoor heated pool open from 5:00am-11:00pm.
  • Affordable Downtown hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Days Inn by Wyndham Middletown in New Hampton
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
4939 Route 17 M, New Hampton, NY 10958 +1-888-788-5576 ~8.43 miles west of Chester
  • Includes a pool: Close
  • Low priced Suburban property
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From$60
Poor 2.0 /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
  • Pool details: 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.
  • 2-star Highway hotel
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From$89
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Homewood Suites Stewart Airport - 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
  • Expensive Rural property
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From$79
Average 3.0 /5 Recent Reviews Call BookMore Details
Courtyard by Marriott Newburgh Stewart Airport - Newburgh
+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
  • Includes a swimming pool
  • 3 star Rural property
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From$114
Average 3.0 /5 Latest Reviews Call BookMore Details
Bear Mountain Inn
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
3020 Seven Lakes Dr., Bear Mountain, NY 10911 +1-888-734-9421 ~14.43 miles east of Chester
  • Pool details: outdoor pool only open Memorial day to Labor day and open to the public
  • Affordable Mountain property
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From$149
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Peekskill in Peekskill
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
2 John Walsh Blvd., Peekskill, NY 10566 +1-888-841-5292 ~17.74 miles east of Chester
  • Pool details: heated indoor pool open from 8am-10pm daily, no lifeguard on duty
  • Affordable Riverfront hotel
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From$97
Average 3.0 /5 Review Score Call BookMore Details
Inn on the Hudson : 634 Main St.
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
634 Main St., Peekskill, NY 10566 +1-888-455-5160 ~18.02 miles east of Chester
  • Pool details: Pool is permanently closes
  • Cheap Riverfront hotel
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From$109
Average 3.0 /5 Read Reviews Call BookMore Details
The Abbey Inn & Spa : 900 Fort Hill Rd.
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
900 Fort Hill Rd., Peekskill, NY 10566 +1-888-965-8297 ~18.02 miles east of Chester
  • Has swimming pool: Seasonal Outdoor Pool: Monday - Friday- 11 am to 7 pm Saturday - Sunday- 10 am - 7:30 pm
  • High end Riverfront hotel
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From$500
Average 3.0 /5 Hotel Reviews Call BookMore Details
Sheraton Mahwah
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
1 International Blvd., Mahwah, NJ 07495 +1-888-906-6358 ~18.10 miles south of Chester
  • Pool available: Indoor heated pool
  • Expensive Suburban hotel
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From$129
Average 3.5 /5 Review Score Call BookMore Details
Courtyard by Marriott Mahwah in Mahwah
+1-888-749-6785

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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 Pool.
  • 3 star Suburban hotel
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites Mahwah - Mahwah
+1-888-878-9982

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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 details: Indoor Pool is open 6AM-11PM Daily.
  • Three Star Suburban hotel
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From$89
Average 3.0 /5 Hotel Reviews Call BookMore Details
DoubleTree by Hilton Mahwah - 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
  • Includes a pool: 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.
  • Midscale Suburban property
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From$105
Average 3.0 /5 Recent Reviews Call BookMore Details
Crystal Springs Resort : 3 Wild Turkey Way
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
3 Wild Turkey Way, Hamburg, NJ 07419 +1-888-389-4121 ~20.60 miles southwest of Chester
  • Includes a pool: Indoor / outdoor pool at Minerals Hotel and at Grand Cascades Lodge.
  • High end Golf Course property
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From$159
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Nanuet
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
270 West Route 59, Nanuet, FL 10954 +1-888-675-2083 ~21.52 miles southeast of Chester
  • Pool available: Indoor Heated Pool & Whirlpool open daily from 5am-10pm
  • 3 star Suburban hotel
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From$500
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Nanuet
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
260 West Route 59, Nanuet, NY 10954 +1-800-716-8490 ~21.59 miles southeast of Chester
  • Has a pool!
  • Midscale Highway property
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From$80
Poor 2.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Poughkeepsie / Fishkill in Fishkill
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
25 Westage Dr., Fishkill, NY 12524 +1-800-805-5223 ~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 .
  • Midscale Highway hotel
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From$99
Very Good 4.0 /5 Recent Reviews Call BookMore Details
HYATT house Fishkill/Poughkeepsie : 100 Westage Business Center Dr.
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
100 Westage Business Center Dr., Fishkill, NY 12524 +1-888-965-1860 ~22.54 miles northeast of Chester
  • Pool available: The HYATT house has an indoor pool whirlpool and fitness center and is open to guests between 8:00am and 10:00pm
  • Mid-scale Suburban hotel
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From$105
Very Good 4.0 /5 Read Reviews Call BookMore Details
Best Western Fishkill Inn & Suites in Fishkill
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
14 Schuyler Blvd., Fishkill, NY 12524 +1-888-788-5576 ~22.68 miles northeast of Chester
  • Pool available: Seasonal Outdoor Pool, located in Patio Area. Open Memorial day Through Labor day.
  • 3-star Suburban hotel
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From$80
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express in Fishkill
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
21 Schuyler Blvd., Fishkill, NY 12524 +1-888-897-9207 ~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.
  • Midscale Suburban hotel
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From$64
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Fishkill - Fishkill
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
544 Us 9, Fishkill, NY 12524 +1-888-311-4278 ~22.77 miles northeast of Chester
  • Includes a pool: Pool is open from 6am-10pm. Recently renovated!
  • Affordable Suburban property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Best Western Hunt's Landing Hotel Matamoras/Milford
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
120 Routes 6 & 209, Matamoras, PA 18336 +1-888-469-4795 ~23.41 miles west of Chester
  • Pool details: This hotel offers an indoor, heated pool; operation hours: 6:00 am-10pm.
  • Cheap Highway hotel
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From$69
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hotel Nyack, a JdV by Hyatt Hotel in Nyack
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
400 High Ave., Nyack, NY 10960 +1-888-734-9421 ~24.98 miles southeast of Chester
  • Pool in hotel: Seasonal Outdoor Pool/ Hot Tub/ Deck 8AM-9PM
  • High-end Suburban property
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From$88
Average 3.0 /5 Guest Reviews Call BookMore Details
Hyatt Place Poughkeepsie
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
2165 South Rd., Poughkeepsie, NY 12601 +1-888-841-5292 ~26.34 miles northeast of Chester
  • Pool details: Swim laps in our indoor pool or elect to relax on a lounger poolside from 8AM - 10PM
  • Midscale Highway hotel
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Poughkeepsie : 2361 South Rd.
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
2361 South Rd., Poughkeepsie, NY 12601 +1-888-455-5160 ~26.76 miles northeast of Chester
  • Includes a pool: Indoor Pool - 8am - 10pm
  • 3-star Suburban property
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From$95
Average 3.0 /5 Latest Reviews Call BookMore Details
Days Inn by Wyndham Wayne : 1850 Nj 23
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
1850 Nj 23, Wayne, NJ 07470 +1-888-965-8297 ~28.14 miles south of Chester
  • Includes a pool: we have out door pool
  • Cheap Suburban property
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From$60
Average 3.0 /5 Reviews Call BookMore Details
Mohonk Mountain House
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
1000 Mountain Rest Rd., New Paltz, NY 12561 +1-888-906-6358 ~29.15 miles north of Chester
  • Has swimming pool: Indoor pool, open 6am to 9am
  • High end Resort property
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From$279
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
The Castle Hotel & Spa : 400 Benedict Ave.
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
400 Benedict Ave., Tarrytown, NY 10591 +1-888-749-6785 ~29.34 miles southeast of Chester
  • Pool in hotel: Outdoor Seasonal Pool & Whirlpool. Open from 10:00 am - 6:00 pm
  • 4-star Suburban property
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From$200
Average 3.0 /5 Reviews Call BookMore Details
Hotel Mtk Mount Kisco - Mount Kisco
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
1 Holiday Inn Dr., Mount Kisco, NY 10549 +1-888-878-9982 ~29.51 miles east of Chester
  • Pool details: Seasonal outdoor pool - open Memorial Day to Labor Day
  • 3 star Suburban hotel
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From$129
Very Good 4.0 /5 Reviews Call BookMore Details
Tarrytown Springhill Suites by Marriott : 480 White Plains Rd.
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
480 White Plains Rd., Tarrytown, NY 10591 +1-888-389-4485 ~29.76 miles southeast of Chester
  • Pool in hotel: Indoor Pool, Open 6AM to 10PM
  • 3-star Suburban property
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From$75
Average 3.0 /5 Reviews Call BookMore Details
Tarrytown House Estate on the Hudson - Tarrytown
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
49 East Sunnyside Lane, Tarrytown, NY 10591 +1-888-389-4121 ~29.84 miles southeast of Chester
  • Pool details: Both indoor and outdoor pool, gym, sauna
  • Three Star Suburban property
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From$89
Average 3.0 /5 Review Score Call BookMore Details
Sheraton Tarrytown Hotel
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
600 White Plains Rd., Tarrytown, NY 10591 +1-888-675-2083 ~30.13 miles southeast of Chester
  • Pool details: 6am- 10pm, indoor pool and hot tub
  • Midscale Suburban hotel
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From$75
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Kartrite Resort Indoor Waterpark
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
555 Resorts World Dr., Monticello, NY 12701 +1-800-716-8490 ~30.17 miles northwest of Chester
  • Has swimming pool: 11am-7pm
  • 3 star Mountain hotel
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From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Monticello
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
16 Raceway Rd., Monticello, NY 12701 +1-800-805-5223 ~31.03 miles northwest of Chester
  • Pool in hotel: Indoor- 8:00 AM to 8:00 PM
  • Midscale Downtown hotel
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From$108
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn in Dobbs Ferry
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
201 Ogden Ave., Dobbs Ferry, NY 10522 +1-888-965-1860 ~31.84 miles southeast of Chester
  • Pool in hotel: Spacious Saltwater Heated pool will be open daily.
  • Affordable Suburban hotel
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Doubletree by Hilton Fairfield Hotel & Suites - Fairfield
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
690 Us 46, Fairfield, NJ 07004 +1-888-788-5576 ~32.08 miles south of Chester
  • Pool details: Indoor Swimming pool open from 6:am - 10:pm daily
  • Mid-scale Suburban property
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From$80
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Rockaway - Rockaway
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
14 Green Pond Rd., Rockaway, NJ 07866 +1-888-897-9207 ~33.04 miles southwest of Chester
  • Pool available: Indoor pool
  • Mid-scale Highway hotel
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From$59
Average 3.0 /5 Guest Reviews Call BookMore Details
Best Western Plus Fairfield Executive Inn - Fairfield
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
216 Route 46 East #234, Fairfield, NJ 07004 +1-888-311-4278 ~33.21 miles south of Chester
  • With a pool!
  • Two star property
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From$95
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn - Denville
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
350 Morris Ave., Denville, NJ 07834 +1-888-469-4795 ~33.21 miles south of Chester
  • Includes a pool: Indoor Heated Pool Hours: 6 am to 11 pm, subject to change.
  • Affordable Highway property
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From$92
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Yonkers in Yonkers
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
160 Corporate Blvd., Yonkers, NY 10701 +1-888-734-9421 ~33.33 miles southeast of Chester
  • Has swimming pool: Indoor pool
  • Three Star Suburban hotel
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Cambria Hotel
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
250 Main St., White Plains, NY 10601 +1-888-841-5292 ~34.20 miles southeast of Chester
  • Pool available: Our pool is open everyday from 6am-midnight.
  • Three Star Downtown property
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From$80
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Parsippany / North
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
3737 Us 46, Parsippany-Troy Hills, NJ 07054 +1-888-455-5160 ~34.32 miles south of Chester
  • Pool in hotel: Indoor Pool Open 6am-10pm
  • 3-star Highway property
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Hotel & Suites Parsippany Fairfield An Ihg Hotel : 707 Us Highway 46 East
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
707 Us Highway 46 East, Parsippany, NJ 07054 +1-888-965-8297 ~34.50 miles south of Chester
  • Pool details: Seasonal Pool open from memorial day weekend to labor day weekend every day from 10am to 8pm
  • Three Star Suburban property
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From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Dover Rockaway in Dover
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
2 Commerce Center Dr., Dover, NJ 07801 +1-888-906-6358 ~34.69 miles southwest of Chester
  • Includes a pool: Indoor pool hours are 9am-10pm Pool is heated.
  • Three Star Suburban property
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From$99
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Parsippany Suites by Hilton - Parsippany-Troy Hills
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
61 Interpace Pkwy., Parsippany-Troy Hills, NJ 07054 +1-888-749-6785 ~34.81 miles south of Chester
  • Pool in hotel: 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
Hyatt House Parsippany East : 299 Smith Rd.
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
299 Smith Rd., Parsippany-Troy Hills, NJ 07054 +1-888-878-9982 ~35.13 miles south of Chester
  • Pool available: Our outdoor pool is OPEN every day from May - October. The deepest level is 4 feet and the shallow limit is 3 feet.
  • 3 star Suburban hotel
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From$50
Very Good 4.0 /5 Latest Reviews Call BookMore Details
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