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Find Hotels with a Pool in Chester, NY

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Check availability on Chester Hotels with a Pool

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Chester hotels with a pool

Indoor pool, sun loungers
Reception
Front of property
Premium bedding, desk, iron/ironing board, WiFi (free)

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester
  • Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
AED 422
AED 520 total
includes taxes & fees
8 Sep - 9 Sep
Holiday Inn Express Hotel & Suites Chester by IHG
Outdoor pool, sun loungers
Miscellaneous
Exterior
Superior Double Room, Ensuite (Primrose) | Miscellaneous

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
  • Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.
AED 790
AED 893 total
includes taxes & fees
13 Aug - 14 Aug
The Dominion House Bed & Breakfast
Exterior
Full breakfast for a fee on weekends
Exterior
Porch

3. The Abbey Inn & Spa

The Abbey Inn & Spa
Peekskill
  • Swim surrounded by lush gardens and historic charm at this peaceful abbey-turned-hotel retreat.
AED 1,230
AED 1,574 total
includes taxes & fees
30 Aug - 31 Aug
The Abbey Inn & Spa
Indoor pool
Free daily self-serve breakfast
Combined shower/tub, free toiletries, hair dryer, towels
Exterior

4. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Peekskill
  • Luxurious indoor pool sanctuary offers year-round aquatic relaxation while overlooking Hudson Valley's scenic landscapes.
AED 481
AED 550 total
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
Lobby
Bar (on property)
Premium bedding, in-room safe, desk, laptop workspace

5. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
Nanuet
  • Sink into this pristine hotel's sun-lounger lined indoor pool and hot tub oasis, just moments from Rockland Lake State Park.
AED 449
AED 522 total
includes taxes & fees
23 Aug - 24 Aug
DoubleTree by Hilton Hotel Nanuet
Indoor pool
Snack bar
Restaurant
Exterior

6. Hampton Inn Fishkill

Hampton Inn Fishkill
Fishkill
  • Splash into an invigorating getaway at this pet-friendly hotel with a pristine indoor pool.
AED 434
AED 501 total
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn Fishkill
Indoor pool
Terrace/patio
Indoor pool
Buffet

7. Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Fishkill
  • Swim under indoor skylights as the hot tub bubbles nearby at this relaxing poolside escape.
AED 463
AED 535 total
includes taxes & fees
10 Sep - 11 Sep
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Seasonal outdoor pool
Suite, Multiple Beds, Non Smoking, Kitchen (with Sofabed) | Desk, laptop workspace, blackout drapes, iron/ironing board
Property amenity
Lobby

8. Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites
Fishkill
  • Seasonal outdoor pool for summer dips makes this hotel a perfect family-friendly getaway.
AED 511
AED 590 total
includes taxes & fees
16 Aug - 17 Aug
Best Western Fishkill Inn & Suites
Indoor pool
Lobby
Lobby
Lobby

9. Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
Fishkill
  • Indoor pool sanctuary with year-round swimming and 24-hour fitness center enhances this hotel in the business district.
AED 449
AED 519 total
includes taxes & fees
30 Aug - 31 Aug
Hilton Garden Inn Fishkill
Indoor pool
Lobby
BBQ/picnic area
Lobby

10. SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill
Fishkill
  • Soak up relaxation at this family-friendly hotel with a pristine indoor pool for year-round swims.
AED 657
AED 760 total
includes taxes & fees
2 Sep - 3 Sep
SpringHill Suites by Marriott Fishkill
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Choose what matters most at hotels with a pool in Chester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chester Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG: Hotel located near LEGOLAND® New York. Features on-the-go, a pool, and complimentary wired internet access. Crowne Plaza Suffern - Mahwah by IHG: Provides continental, an indoor pool, and complimentary wired internet access. Sleep Inn & Suites Middletown - Goshen: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Overlook Lodge at Bear Mountain: Offers daily, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Middletown-Goshen: Features a snack bar/deli, a pool, and free self parking.
What is there to see and do in Chester?
Explore places like LEGOLAND® New York and Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions like The Rock Sports Complex and Castle Fun Center. The restaurants and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Chester?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Chester in the warmest months of July, August, or June when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 32°F.