Search Hotels with Pool in Brewster

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Brewster Hotels with Pool

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Brewster hotels with a pool

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

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (809)
"The inn is absolutely charming! Great staff, clean room and the breakfast buffet was great. We will be returning next year! "
United States
SUSAN
The price is ฿3,582
฿3,882 total
includes taxes & fees
28 Dec - 29 Dec
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, (1001)
"Very lovely hotel "
United States
Nancy M
The price is ฿3,287
฿4,317 total
includes taxes & fees
28 Dec - 29 Dec
Heritage Hotel, Golf, Spa & Conference Center
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, (1002)
"Very nice stay."
United States
Peter
The price is ฿2,797
฿3,164 total
includes taxes & fees
24 Jan - 25 Jan 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
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, (1001)
"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 ฿3,698
฿4,184 total
includes taxes & fees
1 Jan - 2 Jan 2026
Overlook Lodge at Bear Mountain
Seasonal outdoor pool
Ethan Allen Hotel

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
7.8 out of 10, Good, (1092)
"One of my favorite hotel to stay in "
United States
Stephen
Ethan Allen Hotel
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, (1002)
"Yes stay was pleasant "
United States
henry
The price is ฿2,906
฿3,287 total
includes taxes & fees
1 Jan - 2 Jan 2026
Comfort Suites Fishkill near Interstate 84
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, (1003)
"It was a great place to stay "
United States
Amanda
The price is ฿2,848
฿3,221 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hilton Garden Inn Fishkill
Indoor pool
Hampton Inn Fishkill

Hampton Inn Fishkill

Hampton Inn Fishkill
2.5 star property
Fishkill
8.6 out of 10, Excellent, (1000)
"Excellent stay, personnel and breakfast!! "
United States
Wilma L
The price is ฿2,676
฿3,027 total
includes taxes & fees
20 Jan - 21 Jan 2026
Hampton Inn 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, (964)
"Place was amazing "
United States
Neydi
The price is ฿3,291
฿3,723 total
includes taxes & fees
9 Jan - 10 Jan 2026
Best Western Fishkill Inn & Suites
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, (405)
"High marks to this property!! Staff, cleanliness, room layout all excellent!!"
United States
Ron
The price is ฿4,251
฿4,809 total
includes taxes & fees
24 Jan - 25 Jan 2026
Residence Inn by Marriott Fishkill
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

Top Brewster Hotel Reviews

Frequently asked questions

What are some accommodation options 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 high-speed (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 has an outdoor pool if you plan to visit Brewster in the warmest months of July, August or June, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 0°C.
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 venture out into the surrounding area, hop aboard a train at Brewster Train Station or Southeast Station. Brewster might not have many public transport options to choose from, so consider renting a car to explore more.