Brewster Holiday Rentals

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Our top choices for Brewster holiday rentals

Apartment in Brewster

The Hideaway
10.0 out of 10, Exceptional, (7 reviews)
"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 AU$442
includes taxes & fees
6 Mar - 7 Mar
The Hideaway
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$274
includes taxes & fees
4 Mar - 5 Mar
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Camping in New Milford

Creekside Retreat Tent
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$273
includes taxes & fees
18 Mar - 19 Mar
Creekside Retreat Tent
10.0 out of 10, Exceptional, (23 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$178
includes taxes & fees
8 Mar - 9 Mar
Cozy One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (13 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$497
includes taxes & fees
4 Mar - 5 Mar
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
10.0 out of 10, Exceptional, (47 reviews)
"Great place!"
United States
Sara B.
The price is AU$339
includes taxes & fees
5 Mar - 6 Mar
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is AU$430
includes taxes & fees
30 Mar - 31 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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$389
includes taxes & fees
4 Mar - 5 Mar
Charming 1-bedroom apartment in Carmel with WiFi, AC
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$268
includes taxes & fees
16 Mar - 17 Mar
Cozy 1-bedroom retreat minutes from West Point!

Holiday Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AU$580
includes taxes & fees
5 Mar - 6 Mar
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (18 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is AU$682
includes taxes & fees
8 Mar - 9 Mar
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
9.4 out of 10, Exceptional, (61 reviews)
"Best place ever, various entertainment options from projector to tvs. "
United States
Mahbub Ridhoo M.
The price is AU$458
includes taxes & fees
4 Mar - 5 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$301
includes taxes & fees
4 Mar - 5 Mar
The Perch in the Purchase -- Cozy, unique, and private
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is AU$383
includes taxes & fees
4 Mar - 5 Mar
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is AU$317
includes taxes & fees
16 Mar - 17 Mar
Mid Century Modern Studio w/ Full Kitchen - Newly Built
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$470
includes taxes & fees
4 Mar - 5 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!

Apartment in Highland Falls

Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (21 reviews)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
The price is AU$346
includes taxes & fees
4 Mar - 5 Mar
Walk to WP Gate + Free Parking!
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$850
includes taxes & fees
9 Mar - 10 Mar
"Country outside the city " 3 bedrooms 2 full bathrooms
9.8 out of 10, Exceptional, (45 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is AU$335
includes taxes & fees
8 Mar - 9 Mar
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and great place to stay. "
United States
Charlene D.
The price is AU$372
includes taxes & fees
4 Mar - 5 Mar
Stylish & Pet-Friendly Apartment in Beacon
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$339 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 SplashDown Beach. Other places in town to visit include Brewster Public Library and Wells Park.

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.