Title: Book the Best Hotels with POOL in New Windsor in 2026 | Expedia.ca

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Photo by Wanderlustfemale

# Find Hotels with a Pool in New Windsor, NY from CA $133

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## Check availability on New Windsor Hotels with a Pool

Tonight

[Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for New Windsor hotels with a pool

![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds, Non Smoking, Lake View](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/ae84ea2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/cabaefdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/6b6d035b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information)

New Windsor

8.4/10

Very good

(1009)

"Love it, everytime we come this is the place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

CA $125

CA $142 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/e9b6c0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d51e63c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d07e2b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/0e18f638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Homewood Suites Stewart Airport

[](https://www.expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information)

New Windsor

9.2/10

Wonderful

(1001)

"Excellent room extremely clean and amazing and helpful staff"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Philip

CA $175

CA $198 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/a79c4292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/618cd435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/80e497ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/3dad591c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Poughkeepsie

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information)

Crown Heights

8.8/10

Excellent

(1007)

"Great stay with many breakfast options! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sara

CA $126

CA $146 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information)

![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/64788546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/308be1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/1a5890e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Chester by IHG

[](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information)

Chester

8.6/10

Excellent

(1008)

"The breakfast was a hit, the place is clean and I would stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

elizabeth

CA $113

CA $133 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e02a568f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/3b6f022d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2831de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Fishkill

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information)

Fishkill

8.6/10

Excellent

(1007)

"Brayden was great"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Will

CA $126

CA $143 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/17000000/16220000/16211000/16210933/56c94c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/17000000/16220000/16211000/16210933/76b6e8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/17000000/16220000/16211000/16210933/0de7128d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/17000000/16220000/16211000/16210933/6fba2a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence Inn by Marriott Fishkill

[](https://www.expedia.ca/Poughkeepsie-Hotels-Residence-Inn-By-Marriott-Fishkill.h16210933.Hotel-Information)

Fishkill

9.4/10

Exceptional

(403)

"Excellent stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Margaret

CA $188

CA $213 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Poughkeepsie-Hotels-Residence-Inn-By-Marriott-Fishkill.h16210933.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/8626bd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Overlook Lodge at Bear Mountain

[](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information)

Bear Mountain

8.4/10

Very good

(1001)

"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan

CA $145

CA $165 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/73a2acb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ninjago Premium Themed](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/aaa826cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/ded4c5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/67107f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LEGOLAND Hotel NEW York

[](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.Hotel-Information)

Goshen

8.8/10

Excellent

(33)

"We are having a great time at the hotel!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ziwei

CA $262

CA $477 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/e4abb59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/28ad5864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/1712b26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Poughkeepsie / Hudson Valley

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information)

Crown Heights

9.0/10

Wonderful

(1009)

"very clean and would stay again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alvin

CA $139

CA $161 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/a9b4d40a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/7df797b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn by Hilton New Paltz

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information)

New Paltz

9.4/10

Exceptional

(1004)

"The hotel is quiet and clean and had a very comfortable bed."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carolyn

CA $153

CA $172 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-30&endDate=2025-12-31&regionId=10021&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top New Windsor Hotel Reviews

![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg)

### Hampton Inn Harriman Woodbury

10/10 Excellent

"Great location, friendly staff. Highly recommend "

[](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information)

![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg)

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

10/10 Excellent

"Love it, everytime we come this is the place to stay"

[](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information)

![Homewood Suites Stewart Airport](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg)

### Homewood Suites Stewart Airport

10/10 Excellent

"Excellent room extremely clean and amazing and helpful staff"

[](https://expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information)

![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg)

### Courtyard by Marriott Poughkeepsie

10/10 Excellent

"For more than thirty years, every single time I have stayed at a Marriott Hotel, I have been massively impressed with the phenomenal level of customer service, cleanliness and comfortable rooms. Also, I LOVE seeing a lamp next to seating, so I can read a book and lounge, at the same time. Finally, I did not see any of donald trump's gestapo, which was a very good thing."

[](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information)

![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg)

### Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

"Room is perfect for what it is. Clean, quiet very comfortable. "

[](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information)

![Howard Johnson by Wyndham Newburgh/West Point](https://images.trvl-media.com/lodging/1000000/10000/7700/7652/8a35f36a_y.jpg)

### Howard Johnson by Wyndham Newburgh/West Point

10/10 Excellent

"nice bed"

[](https://expedia.ca/Newburgh-Hotels-Howard-Johnson-By-Wyndham-NewburghWest-Point.h7652.Hotel-Information)

![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg)

### Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"😍"

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information)

![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg)

### Hampton Inn by Hilton New Paltz

10/10 Excellent

"The room and bathroom were large, clean, and so much better than I expected for the price! Staff were amazing, very friendly, welcoming and helpful! And the pool was fantastic!! I’d highly recommend Hampton Inn to anyone!"

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information)

![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg)

### Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"Clean, friendly "

[](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information)

## Frequently asked questions

### What are some accommodations with pools in New Windsor?

### What is there to see and do in New Windsor?

### When is the best time to book a hotel with a pool in New Windsor?

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