Find Hotels with a Pool in Brewster, NY

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Check availability on Brewster Hotels with a Pool

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Brewster hotels with a pool

Seasonal outdoor pool, open 8:00 AM to 9:00 PM, free cabanas
Heidi's Inn

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (810)
"The staff was nice and the room was clean."
United States
Mike
The price is ₩179,210
₩194,207 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Heidi's Inn
View from property
Heritage Hotel, Golf, Spa & Conference Center

Heritage Hotel, Golf, Spa & Conference Center

Heritage Hotel, Golf, Spa & Conference Center
3.5 star property
Southbury
8.4 out of 10, Very Good, (1003)
"Very lovely hotel "
United States
Nancy M
The price is ₩157,093
₩205,319 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Heritage Hotel, Golf, Spa & Conference Center
Indoor pool
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (999)
"Yes stay was pleasant "
United States
henry
The price is ₩133,675
₩151,221 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Comfort Suites Fishkill near Interstate 84
Indoor pool
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
2.5 star property
Fishkill
8.4 out of 10, Very Good, (1000)
"Great customer service and breakfast was excellent "
United States
Dennis
The price is ₩129,567
₩146,573 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Sports facility
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1010)
"everything was great "
United States
Christopher
The price is ₩142,010
₩160,649 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hilton Garden Inn Fishkill
Seasonal outdoor pool
Ethan Allen Hotel

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
7.8 out of 10, Good, (1098)
"Great place very accommodating "
United States
Celeste
Ethan Allen Hotel
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1006)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is ₩170,132
₩192,464 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Overlook Lodge at Bear Mountain
Indoor pool
Hampton Inn Fishkill

Hampton Inn Fishkill

Hampton Inn Fishkill
2.5 star property
Fishkill
8.6 out of 10, Excellent, (1002)
"Excellent stay, personnel and breakfast!! "
United States
Wilma L
The price is ₩118,107
₩133,608 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Hampton Inn Fishkill
Indoor pool
Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill
3.0 star property
Fishkill
9.4 out of 10, Exceptional, (408)
"Was clean, staff were friendly, and nice."
United States
Wilson
The price is ₩188,789
₩213,567 total
includes taxes & fees
Jan 31 - Feb 1, 2026
Residence Inn by Marriott Fishkill
Seasonal outdoor pool
Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites
3.5 star property
Fishkill
8.8 out of 10, Excellent, (970)
"Place was amazing "
United States
Neydi
The price is ₩151,417
₩171,291 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Best Western Fishkill Inn & Suites
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.
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Top Brewster Hotel Reviews

The Watershed

The Watershed

10/10 Excellent
"Always an amazing stay, this is my 5th time here and my family and I are never disappointed. The staff are awesome and accommodating and the hotel is always clean and smells great!!"
Malissa 1-night trip
Posted 3 days ago
The Watershed

Frequently asked questions

What are some accommodations with pools in Brewster?
Comfort Inn Brewster: Offers daily, a seasonal outdoor pool, and free self parking. Heidi's Inn: Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. EVEN Hotel Norwalk by IHG: Features a snack bar/deli, a seasonal outdoor pool, and free self parking. Overlook Lodge at Bear Mountain: Offers daily, a seasonal outdoor pool, and free self parking. Windrose On Hudson: Provides complimentary wired internet access, a pool, and free self parking.
What is there to see and do in Brewster?
Take a walk along the waterfront at Mamanasco Beach and Canopus Beach. Discover sights such as Brewster Public Library during your stay.
When is the best time to book a hotel with a pool in Brewster?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Brewster in the warmest months of July, August, or June when the average temp is 69°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.
What's the best way to travel around Brewster?
Knowing the transportation options in Brewster can help you enjoy the area beyond your hotel pool. To see more of the surrounding area, hop aboard a train at Brewster Train Station or Southeast Station. Brewster may not have many public transit options to choose from so consider renting a car to explore more.