Brewster Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Brewster vacation rentals

Property grounds
The Hideaway

Apartment in Brewster

The Hideaway
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is ￥24,268
￥49,208 total
includes taxes & fees
Dec 30 - Dec 31
The Hideaway
Property grounds
Creekside Retreat Tent

Camping in New Milford

Creekside Retreat Tent
10.0 out of 10, Exceptional, (4)
"Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ."
United States
yarelis t.
The price is ￥23,486
￥30,140 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Creekside Retreat Tent
Exterior
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1.0 star property
8.0 out of 10, Very Good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is ￥23,486
￥30,140 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Microwave, oven, stovetop, dishwasher
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Apartment in Southbury

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥13,387
￥18,527 total
includes taxes & fees
Jan 6 - Jan 7, 2026
New One Bedroom Apartment Centrally Located in Southbury
Interior
Contemporary Cozy Cottage

Vacation Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥35,228
￥65,363 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Contemporary Cozy Cottage
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Apartment in Kent

Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.8 out of 10, Exceptional, (10)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥30,531
￥38,555 total
includes taxes & fees
Dec 30 - Dec 31
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Apartment in New Fairfield

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
10.0 out of 10, Exceptional, (34)
"Stunning property!!"
United States
Samantha
The price is ￥38,751
￥69,616 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥26,069
￥55,570 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining
Updated, cozy single family in Fairfield County

Vacation Home in Trumbull

Updated, cozy single family in Fairfield County
9.4 out of 10, Exceptional, (12)
"This location is great close to highway and mall."
United States
Sansia D.
The price is ￥33,608
￥73,486 total
includes taxes & fees
Dec 30 - Dec 31
Updated, cozy single family in Fairfield County
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cottage in Fort Montgomery

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is ￥29,435
￥47,646 total
includes taxes & fees
Dec 30 - Dec 31
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in CROTON HDSN

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is ￥17,595
￥42,869 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Smart TV, fireplace, books
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Vacation Home in New Fairfield

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
10.0 out of 10, Exceptional, (16)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Vacation Home in Hopewell Junction

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is ￥23,814
￥40,403 total
includes taxes & fees
Dec 30 - Dec 31
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
3 bedrooms, iron/ironing board, travel crib, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

Vacation Home in Holmes

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥29,451
￥84,681 total
includes taxes & fees
Jan 6 - Jan 7, 2026
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior
Rustic Cabin in Fishkill!

Cabin in Fishkill

Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥47,362
￥70,774 total
includes taxes & fees
Dec 30 - Dec 31
Rustic Cabin in Fishkill!
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥21,137
￥43,439 total
includes taxes & fees
Dec 30 - Dec 31
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Apartment in Croton-on-Hudson

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is ￥16,275
￥37,955 total
includes taxes & fees
Jan 4 - Jan 5, 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Apartment in Highland Falls

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is ￥25,646
￥43,919 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Fridge, microwave, oven, stovetop
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Apartment in Beacon

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
10.0 out of 10, Exceptional, (46)
"Great location, so clean and comfortable. "
United States
Barbara
The price is ￥18,006
￥38,936 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Spotlessly clean, attractive lobby, welcoming efficient staff for check-in, large , comfortable room, convenient to eateries and shopping and outdoor activities "
kay 1-night trip
Posted 2 days ago
Quality Inn & Suites Fishkill South near I-84

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Brewster offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Kouros Sculpture Center, or visit a family-friendly sight such as SplashDown Beach. Brewster Public Library and Lake Mahopac are a couple of places you'll find in the larger area.

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.