The Best Hotels with a Pool in Chester, NY from ￥17,882 in 2026

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Our top choices for Chester hotels with a pool

Premium bedding, desk, iron/ironing board, WiFi (free)

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.

￥19,127

￥23,549 total

includes taxes & fees

Sep 17 - Sep 18

Superior Double Room, Ensuite (Primrose) | Miscellaneous

2. The Dominion House Bed & Breakfast

Chester

Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.

￥33,164

￥37,517 total

includes taxes & fees

Sep 28 - Sep 29

3. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

Chester

￥383,466

￥604,501 total

includes taxes & fees

Sep 30 - Oct 1

4. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.

￥21,563

￥26,551 total

includes taxes & fees

Sep 27 - Sep 28

One King Bed Studio | Living area | 55-inch LCD TV with cable channels, TV, pay movies

5. Hampton Inn Harriman Woodbury

Central Valley

Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.

￥17,697

￥21,790 total

includes taxes & fees

Sep 22 - Sep 23

Premium bedding, pillowtop beds, desk, laptop workspace

Rainfall showerhead, free toiletries, hair dryer, towels

6. La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

Immerse in a serene aquatic escape at this family-friendly hotel featuring a pristine indoor pool and relaxation hot tub.

￥20,685

￥24,435 total

includes taxes & fees

Sep 21 - Sep 22

7. Candlewood Suites Middletown Goshen by IHG

Middletown

￥18,202

￥21,501 total

includes taxes & fees

Oct 4 - Oct 5

Efficiency, Suite, 1 King Bed, Non Smoking | Premium bedding, desk, soundproofing, iron/ironing board

8. Sleep Inn & Suites Middletown - Goshen

Middletown

Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.

￥16,914

￥19,980 total

includes taxes & fees

Oct 13 - Oct 14

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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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

8/10 Good

"Everything was nice and clean ..good service and staff uncomfortable pillows my only complaint"

Mountain Creek

10/10 Excellent

"Quiet and remote location"

Hampton Inn & Suites Mahwah

10/10 Excellent

"Great friendly staff clean hotel with breakfast downstairs was great"

Hilton Garden Inn Nanuet

10/10 Excellent

"Property is old and could use a redo. But the property is well maintained. Rooms were clean and comfortable."

Ramada by Wyndham Newburgh/West Point

10/10 Excellent

"Non"

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. Overlook Lodge at Bear Mountain: Hotel, 1-minute walk from Bear Mountain State Park. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Sleep Inn & Suites Middletown - Goshen: Provides continental, an indoor pool, and complimentary wired internet access. Crowne Plaza Suffern - Mahwah by IHG: Offers buffet, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Middletown-Goshen: Hotel, 1-minute walk from Mountain Creek Ski Resort. Features a sauna, an outdoor pool, and a snack bar/deli.

What is there to see and do in Chester?

Explore places like 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.

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Check availability on Chester Hotels with a Pool

Our top choices for Chester hotels with a pool

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. The Dominion House Bed & Breakfast

3. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

4. Fairfield Inn & Suites by Marriott Goshen Middletown

5. Hampton Inn Harriman Woodbury

6. La Quinta Inn & Suites by Wyndham Middletown-Goshen

7. Candlewood Suites Middletown Goshen by IHG

8. Sleep Inn & Suites Middletown - Goshen

9. Courtyard by Marriott Middletown Goshen

10. Holiday Inn Express & Suites Middletown - Goshen by IHG

Choose what matters most at hotels with a pool in Chester

Top Chester Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Mountain Creek

Hampton Inn & Suites Mahwah

Hilton Garden Inn Nanuet

Ramada by Wyndham Newburgh/West Point

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with a Pool in Chester, NY

Change your mind

Treat yourself

Be picky

Check availability on Chester Hotels with a Pool

Our top choices for Chester hotels with a pool

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. The Dominion House Bed & Breakfast

3. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

4. Fairfield Inn & Suites by Marriott Goshen Middletown

5. Hampton Inn Harriman Woodbury

6. La Quinta Inn & Suites by Wyndham Middletown-Goshen

7. Candlewood Suites Middletown Goshen by IHG

8. Sleep Inn & Suites Middletown - Goshen

9. Courtyard by Marriott Middletown Goshen

10. Holiday Inn Express & Suites Middletown - Goshen by IHG

Choose what matters most at hotels with a pool in Chester

Top Chester Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Mountain Creek

Hampton Inn & Suites Mahwah

Hilton Garden Inn Nanuet

Ramada by Wyndham Newburgh/West Point

Frequently asked questions

Explore a world of travel with Expedia