Brewster Holiday Rentals

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Our top choices for Brewster holiday rentals

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (6 reviews)
"I will definitely stay there when I come up north again. The accommodations were very comfortable and well supplied. As an added bonus with a wonderful cats that came around for loving"
United States
Cindy S.
The price is AU$469
includes taxes & fees
17 Jan - 18 Jan
The Hideaway

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1.0 star property
New Milford
8.0 out of 10, Very good, (1 review)
"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 AU$290
includes taxes & fees
17 Jan - 18 Jan
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (21 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$191
includes taxes & fees
18 Jan - 19 Jan
Cozy One Bedroom Apartment Centrally Located in Southbury

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, (15 reviews)
"Great Unit."
United States
Rudy R.
The price is AU$387
includes taxes & fees
19 Jan - 20 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is AU$284
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroom retreat minutes from West Point!

The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
2.0 star property
Southbury
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$310
includes taxes & fees
19 Jan - 20 Jan
The Perch in the Purchase -- Cozy, unique, and private

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$513
includes taxes & fees
22 Jan - 23 Jan
House on the Babbling Brook- Quiet 2BR + King Bed!

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is AU$581
includes taxes & fees
20 Jan - 21 Jan
Sleek Escape: Modern 3 BR- 4 Min from West Point !

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is AU$353
includes taxes & fees
20 Jan - 21 Jan
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is AU$547
includes taxes & fees
20 Jan - 21 Jan
Local Artist Inspired | Walk to WestPoint + King Bed

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90 reviews)
"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 AU$432
includes taxes & fees
20 Jan - 21 Jan
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (10 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is AU$376
includes taxes & fees
27 Jan - 28 Jan
Mid Century Modern Studio w/ Full Kitchen - Newly Built

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 AU$413
includes taxes & fees
17 Jan - 18 Jan
Charming 1-bedroom apartment in Carmel with WiFi, AC

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.0 out of 10, Wonderful, (10 reviews)
"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 AU$385
includes taxes & fees
24 Jan - 25 Jan
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is AU$461
includes taxes & fees
18 Jan - 19 Jan
Lovely 3BR Home with parking-Walk to WP Gate!

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, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is AU$366
includes taxes & fees
19 Jan - 20 Jan
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

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, (12 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is AU$527
includes taxes & fees
21 Jan - 22 Jan
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Creekside Retreat Tent

Creekside Retreat Tent
New Milford
10.0 out of 10, Exceptional, (4 reviews)
"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 AU$290
includes taxes & fees
18 Jan - 19 Jan
Creekside Retreat Tent

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
7.6 out of 10, Good, (5 reviews)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
The price is AU$647
includes taxes & fees
22 Jan - 23 Jan
3BR West Point Retreat-3min to Back Gate+ King Bed

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AU$847
includes taxes & fees
26 Jan - 27 Jan
"Country outside the city " 3 bedrooms 2 full bathrooms
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

Everything you need to know about Brewster holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Brewster holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brewster holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Brewster holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brewster. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Brewster holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Brewster holiday rentals we have selected for you start as low as AU$191 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Brewster rentals

At Expedia, we put the best Brewster holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Brewster rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brewster holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brewster. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Brewster?

Yes, there are holiday rentals close to the most popular sights in Brewster, or you can select a more 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 are some of the best holiday rentals that Brewster has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday 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 an electric kettle, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Brewster?

With 3 Expedia holiday rentals, you're guaranteed 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 one of the family-friendly sights such as Grand Prix New York / Spins Bowl. Brewster Public Library and Matrix Conference and Banquet Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Brewster like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brewster. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.