Brewster Vacation Rentals

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Our top choices for Brewster vacation rentals

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (8 reviews)
"Nice, clean, comfortable place to stay. Beautiful, convenient setting. Will look to come back again some day for sure. "
United States
Kenneth M.
The price is CA $214
CA $433 total
includes taxes & fees
May 25 - May 26
The Hideaway

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is CA $110
CA $184 total
includes taxes & fees
May 25 - May 26
Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is CA $110
CA $184 total
includes taxes & fees
May 25 - May 26
Glamping, family fun, pet friendly

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (28 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is CA $130
CA $177 total
includes taxes & fees
May 25 - May 26
Cozy One Bedroom Apartment Centrally Located in Southbury

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
The price is CA $124
CA $140 total
includes taxes & fees
Jun 3 - Jun 4
1 King Bed | Non-Smoking, Kitchen, Shower

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is CA $152
CA $285 total
includes taxes & fees
May 25 - May 26
Hoppy Hill Farm House

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
10.0 out of 10, Exceptional, (7 reviews)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
The price is CA $138
CA $317 total
includes taxes & fees
May 25 - May 26
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
Updated Home w/ Patio Half Mile to West Point

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean, overall terrific!"
United States
Daniel M.
The price is CA $159
CA $342 total
includes taxes & fees
Jun 23 - Jun 24
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen
Fishkill
10.0 out of 10, Exceptional, (15 reviews)
"Good so far"
United States
Anonymous traveller
The price is CA $124
CA $140 total
includes taxes & fees
Jun 3 - Jun 4
1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is CA $186
CA $382 total
includes taxes & fees
May 24 - May 25
Charming 1-bedroom apartment in Carmel with WiFi, AC

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is CA $682
CA $980 total
includes taxes & fees
May 25 - May 26
Chestnut on Willow Lake

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay. Cozy, warm, and clean! The host was also a good communicator and everything went smoothly."
United States
Samantha Esmé W.
The price is CA $158
CA $333 total
includes taxes & fees
May 31 - Jun 1
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is CA $1,201
CA $2,026 total
includes taxes & fees
May 28 - May 29
Summer Pool Oasis Custom Bar Arcade Pool Table

Studio 6 Fishkill|King bed|Hearing Access|Kitchen

Studio 6 Fishkill|King bed|Hearing Access|Kitchen
Fishkill
10.0 out of 10, Exceptional, (18 reviews)
"great place to stay"
United States
Anonymous traveller
The price is CA $142
CA $164 total
includes taxes & fees
Jun 1 - Jun 2
Studio 6 Fishkill|King bed|Hearing Access|Kitchen

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is CA $279
CA $739 total
includes taxes & fees
May 26 - May 27
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (138 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is CA $273
CA $459 total
includes taxes & fees
May 25 - May 26
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is CA $158
CA $428 total
includes taxes & fees
May 27 - May 28
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is CA $310
CA $587 total
includes taxes & fees
May 25 - May 26
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (6 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is CA $297
CA $572 total
includes taxes & fees
May 27 - May 28
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
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

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.

Frequently asked questions

Can I find a vacation rental in Brewster?

Yes, we offer vacation rentals close to popular local attractions in Brewster, or you can choose a secluded option if you're looking for a relaxing stay. Brewster is known for its shopping and restaurants. Make sure you have time to check out the entertainment choices and live music during your trip.

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

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This vacation home rental outside of Brewster is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Brewster?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Brewster stay.

What’s there to see and do in Brewster?

Explore the area and cultural attractions such as Ives Concert Park, or visit a family-friendly sight such as SplashDown Beach. Other places in town to visit include Brewster Public Library and Wells Park.

What’s a vacation rental in Brewster like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Brewster. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.