Title: Brewster Vacation Rentals from CA $164: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Brewster](https://expedia.ca/Brewster-Hotels.d183644.Travel-Guide-Hotels)[Flights to Brewster](https://expedia.ca/Cheap-Flights-To-Brewster.d183644.Travel-Guide-Flights)[Things to do in Brewster](https://expedia.ca/Things-To-Do-In-Brewster.d183644.Travel-Guide-Activities)[Brewster Car Rentals](https://expedia.ca/Car-Rentals-In-Brewster.d183644.Car-Rental-Guide)[Brewster Vacation Packages](https://expedia.ca/Brewster.d183644.Destination-Travel-Guides)

![East Branch Reservoir in Brewster New York](https://images.trvl-media.com/place/183644/6f27c7a3-5688-4530-9f7d-55c36bf42038.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/183644/6f27c7a3-5688-4530-9f7d-55c36bf42038.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=183644&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Brewster vacation rentals

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6e503ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/w3000h1944x0y0-bf620bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/11e211e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW 45 Wolden Rd Ossining NY 10562

[](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information)

Ossining

CA $563

CA $1,271 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.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=2026-02-18&endDate=2026-02-19&regionId=183644&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APART_HOTEL)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Brewster%2C+New+York%2C+United+States+of+America&regionId=183644&latLong=41.397316%2C-73.617073&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CHALET)

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## Top Brewster Hotel Reviews

![The Watershed](https://images.trvl-media.com/lodging/7000000/6030000/6020100/6020007/c1a1bbc5_y.jpg)

### The Watershed

10/10 Excellent

"Beautiful hotel. Rooms are spacious and updated. The staff are absolutely wonderful. I highly recommend. The bed was comfy and the bathroom was updated and spotless. "

[](https://expedia.ca/Stamford-Hotels-Hotel-Zero-Degrees-Norwalk.h6020007.Hotel-Information)

![Hampton Inn Danbury](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/5476c121_y.jpg)

### Hampton Inn Danbury

10/10 Excellent

"The staff was very efficient and friendly. The room was clean and comfortable. Breakfast was a bonus!"

[](https://expedia.ca/Danbury-Hotels-Hampton-Inn-Danbury.h1445733.Hotel-Information)

![Hilton Garden Inn Fishkill](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350_y.jpg)

### Hilton Garden Inn Fishkill

10/10 Excellent

"Room was beautifully spotless. Enjoyed everything during my stay."

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

![The Thayer Hotel at West Point](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/c0c1b35f_y.jpg)

### The Thayer Hotel at West Point

10/10 Excellent

"Everything about the Thayer is amazing. From the food to the people to the room to the views. Love love love!!"

[](https://expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information)

![Heidi's Inn](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/0ce6450f_y.jpg)

### Heidi's Inn

10/10 Excellent

"all was good"

[](https://expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information)

![Extended Stay America Suites Norwalk Stamford](https://images.trvl-media.com/lodging/1000000/290000/280600/280539/3f2892d7_y.jpg)

### Extended Stay America Suites Norwalk Stamford

10/10 Excellent

"The room was quite nice and comfortable. Sasha was very helpful in regards to a situation. I loved how their was an option to have the added on essentials of dish wear and such. I was not very fond of the grab and go style of breakfast. Overall it was a great stay for two nights. "

[](https://expedia.ca/Stamford-Hotels-Extended-Stay-America-Suites-Norwalk-Stamford.h280539.Hotel-Information)

![HYATT house Fishkill/Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/4a7fc30b_y.jpg)

### HYATT house Fishkill/Poughkeepsie

10/10 Excellent

"Chris and Jennifer went above and beyond working with us the rooms are fantastic the pool was clean a tub was great kitchen was great"

[](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information)

![Hotel Hi-Ho - Contactless Check-In](https://images.trvl-media.com/lodging/13000000/12360000/12354500/12354480/c5fc9bff_y.jpg)

### Hotel Hi-Ho - Contactless Check-In

10/10 Excellent

"Extremely clean room, quiet and comfortable, great heating/ac unit and a liquor store literally right next door! Couldn’t ask for a better, more affordable hotel. Loved it. "

[](https://expedia.ca/New-Haven-Hotels-Hi-Ho-A-Hi-Tech-Hotel.h12354480.Hotel-Information)

![EVEN Hotel Norwalk by IHG](https://images.trvl-media.com/lodging/1000000/10000/2600/2584/4cb7d7eb_y.jpg)

### EVEN Hotel Norwalk by IHG

10/10 Excellent

"Super clean, friendly "

[](https://expedia.ca/Stamford-Hotels-EVEN-Hotel-Norwalk.h2584.Hotel-Information)

## Find out more about Brewster

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Brewster. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Brewster ](https://expedia.ca/Brewster-Private-Vacation-Homes.d183644-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Brewster ](https://expedia.ca/Brewster-Cottages.d183644-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Brewster ](https://expedia.ca/Brewster-Apartments.d183644-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Brewster ](https://expedia.ca/Brewster-Cabins.d183644-aaCabins.Travel-Guide-Accommodation)
- [Motels in Brewster ](https://expedia.ca/Brewster-Motels.d183644-aaMotels.Travel-Guide-Accommodation)
- [Aparthotels in Brewster ](https://expedia.ca/Brewster-Apart-Hotels.d183644-aaApartHotels.Travel-Guide-Accommodation)
- [B&B in Brewster ](https://expedia.ca/Brewster-Bed-And-Breakfast.d183644-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Brewster ](https://expedia.ca/Brewster-Guest-Houses.d183644-aaGuestHouses.Travel-Guide-Accommodation)
- [Farmstay in Brewster ](https://expedia.ca/Brewster-Agritourism.d183644-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Brewster ](https://expedia.ca/Brewster-Villas.d183644-aaVillas.Travel-Guide-Accommodation)
- [RV Parks in Brewster ](https://expedia.ca/Brewster-RV-Parks.d183644-aaRVParks.Travel-Guide-Accommodation)
- [Inns in Brewster ](https://expedia.ca/Brewster-Inns.d183644-aaInns.Travel-Guide-Accommodation)
- [Condo Rentals in Brewster ](https://expedia.ca/Brewster-Condos.d183644-aaCondos.Travel-Guide-Accommodation)
- [Chalets in Brewster ](https://expedia.ca/Brewster-Chalets.d183644-aaChalets.Travel-Guide-Accommodation)
- [Hostels in Brewster ](https://expedia.ca/Brewster-Hostels.d183644-aaHostels.Travel-Guide-Accommodation)
- [Lodges in Brewster ](https://expedia.ca/Brewster-Lodges.d183644-aaLodges.Travel-Guide-Accommodation)
- [Castles in Brewster ](https://expedia.ca/Brewster-Castles.d183644-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Brewster?

### What's the top vacation rental that Brewster has to offer?

### How many vacation rentals are there in Brewster?

### What’s there to see and do in Brewster?

### What’s a vacation rental in Brewster like?

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