The Best Hotels with an Indoor Pool in Chester, NY from AED 352 in 2026

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Our top choices for Chester hotels with an indoor pool

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

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

AED 439 total

includes taxes & fees

15 Nov - 16 Nov

A lobby with a fireplace, seating area, and a reception desk.

2. Hampton Inn Harriman Woodbury

Central Valley

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

AED 534 total

includes taxes & fees

15 Nov - 16 Nov

3. 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.

AED 490 total

includes taxes & fees

6 Dec - 7 Dec

A hotel with a modern facade, multiple floors, and a covered entrance area.

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

Middletown

Make a splash in this hotel's tranquil indoor pool, steps away from LEGOLAND® New York.

AED 417 total

includes taxes & fees

6 Dec - 7 Dec

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

5. Sleep Inn & Suites Middletown - Goshen

Middletown

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

AED 456 total

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

6. Residence Inn by Marriott Middletown Goshen

Middletown

Take a dip in the modern indoor pool at this Goshen hotel, offering year-round swimming in a spotlessly clean aquatic retreat.

AED 777 total

includes taxes & fees

29 Nov - 30 Nov

A landscaped outdoor area with a fire feature, seating, and a pathway.

7. Courtyard by Marriott Middletown Goshen

Middletown

Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.

AED 457 total

includes taxes & fees

19 Nov - 20 Nov

An outdoor patio area with seating, a fire feature, and a view of the surrounding buildings.

8. Home2 Suites by Hilton Middletown

Middletown

Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.

AED 673 total

includes taxes & fees

16 Nov - 17 Nov

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

9. Homewood Suites Stewart Airport

New Windsor

Dive into blissful relaxation at this hotel's indoor pool oasis with bubbling hot tub escape.

AED 686 total

includes taxes & fees

4 Dec - 5 Dec

A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

10. Candlewood Suites Middletown Goshen by IHG

Middletown

AED 512 total

includes taxes & fees

7 Dec - 8 Dec

View all properties

Top Chester Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

10/10 Excellent

Edward J

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

10/10 Excellent

Jordan

Residence Inn by Marriott Middletown Goshen

Middletown

10/10 Excellent

Everything was beautiful, it looks like a new property. My only complaint was after shutting off the air conditioner/heater it still remained on and was very noisy keeping my wife and I up most of the night. Even switching the circuit breaker off didn’t solve the problem. I’m not one to complain though and didn’t bother the staff at the late hour. I still wouldn’t hesitate to stay at a residence inn property in the future.

Joseph

Holiday Inn Express & Suites Middletown - Goshen by IHG

Middletown

10/10 Excellent

Kathleen

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.

Anonymous traveler

Sleep Inn & Suites Middletown - Goshen

Middletown

10/10 Excellent

Damion

Candlewood Suites Middletown Goshen by IHG

Middletown

10/10 Excellent

Moraivic

Home2 Suites by Hilton Middletown

Middletown

10/10 Excellent

Anonymous traveler

Courtyard by Marriott Middletown Goshen

Middletown

10/10 Excellent

Kathleen

An outdoor patio area with a stone fire pit, seating, and a Marriott sign in the background.

SpringHill Suites by Marriott Fishkill

Fishkill

10/10 Excellent

MICHELLE

A buffet with various food items, including omelets and baked goods, served in metal containers.

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

Peekskill

10/10 Excellent

David Allen

A modern kitchen with dark cabinets, a stainless steel microwave, and a white countertop.

HYATT house Fishkill/Poughkeepsie

Fishkill

10/10 Excellent

Monica

A buffet with various food items, including omelets and other dishes, arranged in metal serving trays.

Holiday Inn Express Haskell - Wayne Area by IHG

Wanaque

10/10 Excellent

Christine

A Red Roof Inn & Suites building with a two-story structure, a balcony, and an American flag.

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

New Windsor

10/10 Excellent

Belinda

Frequently Asked Questions

What are some of the best hotels in Chester with indoor pools?

Holiday Inn Express Hotel & Suites Chester by IHG is a short walk from Castle Fun Center and features an indoor pool, as well as on-the-go, complimentary wired internet access, free self parking, and flat-screen televisions.

On top of hotels with indoor pools, what does Chester have to offer?

Enjoy the shopping and excursions in Chester accompanied by accommodation with an indoor pool for some easy access R&R. Don't miss the restaurants in Chester—prepare to be entertained from sunrise to sunset.

What is there to do in Chester?

After several relaxing laps in the pool, head out and visit some of the top attractions in and around Chester. Consider a trip to Castle Fun Center, Museum Village, and The Rock Sports Complex. A few other contenders are Goosepond Mountain State Park and Sugar Loaf Performing Arts Center.

Why should I choose a hotel with an indoor pool for my stay in Chester?

An accommodation with an indoor pool is ideal for a weekend in Chester in all seasons, as it provides a lovely way to spend the time should the weather turn. An indoor pool is perfect for staying active when adjusting to the time difference if you're coming from far away.

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Find Hotels with an Indoor Pool in Chester, NY

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester hotels with an indoor pool

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. Hampton Inn Harriman Woodbury

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

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

5. Sleep Inn & Suites Middletown - Goshen

6. Residence Inn by Marriott Middletown Goshen

7. Courtyard by Marriott Middletown Goshen

8. Home2 Suites by Hilton Middletown

9. Homewood Suites Stewart Airport

10. Candlewood Suites Middletown Goshen by IHG

Top Chester Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

Frequently Asked Questions

What are some of the best hotels in Chester with indoor pools?

On top of hotels with indoor pools, what does Chester have to offer?

What is there to do in Chester?

Why should I choose a hotel with an indoor pool for my stay in Chester?

Explore a world of travel with Expedia