Brewster Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Brewster vacation rentals

Living area

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 ￥24,605
￥49,546 total
includes taxes & fees
May 26 - May 27
The Hideaway
Property grounds

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 ￥12,715
￥21,209 total
includes taxes & fees
May 26 - May 27
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Outdoor dining

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 ￥12,715
￥21,209 total
includes taxes & fees
May 27 - May 28
Glamping, family fun, pet friendly
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (27 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 ￥15,724
￥21,259 total
includes taxes & fees
May 25 - May 26
Cozy One Bedroom Apartment Centrally Located in Southbury
Lobby

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is ￥14,305
￥16,183 total
includes taxes & fees
Jun 14 - Jun 15
1 King Bed | Non-Smoking, Kitchen, Shower
Property grounds

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 ￥17,461
￥32,683 total
includes taxes & fees
May 27 - May 28
Hoppy Hill Farm House
Property grounds

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 ￥18,265
￥38,557 total
includes taxes & fees
May 25 - May 26
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
House (3 Bedrooms) | Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is ￥38,913
￥98,749 total
includes taxes & fees
Jun 2 - Jun 3
Updated Home w/ Patio Half Mile to West Point
Dining

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 ￥17,461
￥38,194 total
includes taxes & fees
Jun 2 - Jun 3
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Lobby

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 traveler
The price is ￥14,281
￥16,154 total
includes taxes & fees
Jun 4 - Jun 5
1 Queen Bed | ADA/RI Shower/Smoking/Kitchen
Private 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 ￥21,430
￥43,696 total
includes taxes & fees
May 24 - May 25
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior

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 ￥78,576
￥112,978 total
includes taxes & fees
May 26 - May 27
Chestnut on Willow Lake
Exterior detail

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 ￥18,265
￥38,583 total
includes taxes & fees
May 26 - May 27
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Villa | 5 bedrooms

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is ￥123,129
￥216,456 total
includes taxes & fees
May 20 - May 21
Westchester Summer Pool Pet Friendly Events Games
Exterior

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 traveler
The price is ￥16,372
￥18,929 total
includes taxes & fees
Jun 1 - Jun 2
Studio 6 Fishkill|King bed|Hearing Access|Kitchen
Exterior detail

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 ￥33,018
￥81,710 total
includes taxes & fees
May 20 - May 21
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Property grounds

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, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ￥31,431
￥50,254 total
includes taxes & fees
May 20 - May 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fridge, oven, stovetop, coffee/tea maker

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 ￥18,255
￥48,712 total
includes taxes & fees
May 27 - May 28
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
TV, fireplace

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 ￥32,145
￥62,534 total
includes taxes & fees
May 21 - May 22
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Smart TV, video games, DVD player, books

'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 ￥35,422
￥66,854 total
includes taxes & fees
May 26 - May 27
'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

Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

2/10 Terrible
"We never ended up.staying there. We arrived at 9 pm. There.was a sign at.thenfront desk staing that the hotel.was sold out and that noone would be back at the desk.until.9.am the next day. Several.long term sta6 guests said the place.was.terribly run. Hotels.com should remove them.from the listnof.choices. DO NOT BOOK THIS PLACE."
Louise 1-night trip
Posted 8 hours ago
Studio 6 Extended Stay Fishkill Westage Center NY

Find out more about Brewster

Search for holiday rentals in Brewster on Expedia! You can easily find your home rentals, villas, holiday apartments in Brewster using one of the methods below:

  • View our selection of featured holiday rentals in Brewster
  • Use the map to find apartments and other holiday homes in the Brewster neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Brewster while they last

Look no further and take a look at our great range of rental properties in Brewster!

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.