Brewster Holiday Rentals

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Holiday Rentals in Brewster

Cozy cute Relaxing home

8.6 out of 10, Excellent, (4)
"nice quiet area"
Cozy cute Relaxing home

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

The price is AU$3,705
includes taxes & fees
18 July - 19 July
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

Renovated Retreat | Heated Saltwater Pool | BBQ

The price is AU$1,456
includes taxes & fees
3 Aug - 4 Aug
Renovated Retreat | Heated Saltwater Pool | BBQ

The West Lane Inn - Queen Room

9.4 out of 10, Exceptional, (3)
"Vert nice property, very nice and accommodating proprietor and staff."
The price is AU$654
includes taxes & fees
27 July - 28 July
The West Lane Inn - Queen Room

Awesome Lake Home with tons of fun!

2.0 star property
The price is AU$1,203
includes taxes & fees
22 July - 23 July
Awesome Lake Home with tons of fun!

Mid Century Modern Studio w/ Full Kitchen - Newly Built

8.0 out of 10, Very good, (1)
"Super cute, clean, and convenient for our quick trip to The Millbrook School."
The price is AU$386
includes taxes & fees
20 July - 21 July
Mid Century Modern Studio w/ Full Kitchen - Newly Built

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

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
The price is AU$620
includes taxes & fees
22 July - 23 July
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (15)
"We had a great stay and had everything we needed!"
The price is AU$1,234
includes taxes & fees
21 July - 22 July
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Summer Castle: Pool, Game Room, BBQ - Pet Friendly

8.0 out of 10, Very good, (3)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is AU$2,138
includes taxes & fees
28 July - 29 July
Summer Castle: Pool, Game Room, BBQ - Pet Friendly

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (9)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is AU$399
includes taxes & fees
20 July - 21 July
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (24)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is AU$640
includes taxes & fees
27 July - 28 July
Contemporary Cozy Cottage

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is AU$650
includes taxes & fees
21 July - 22 July
Rustic Cabin in Fishkill!

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
The price is AU$907
includes taxes & fees
28 July - 29 July
Chestnut on Willow Lake

Hickory on Willow Lake

9.0 out of 10, Wonderful, (2)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is AU$952
includes taxes & fees
23 July - 24 July
Hickory on Willow Lake

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

6.0 out of 10, (1)
"Property was very clean and nicely decorated. There isn’t really a living room to hang out. Very difficult for 3 adults to all hang out together. When I booked I was more concerned about the sleeping area so I assumed there was a living room. The guest suite is in the basement of home in a nice neighborhood."
The price is AU$385
includes taxes & fees
20 July - 21 July
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (24)
"Plenty of room for my family"
The price is AU$511
includes taxes & fees
20 July - 21 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is AU$1,268
includes taxes & fees
20 July - 21 July
West Point Family Retreat, 5 min walk to Thayer!

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

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is AU$518
includes taxes & fees
5 Aug - 6 Aug
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is AU$523
includes taxes & fees
6 Aug - 7 Aug
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is AU$2,016
includes taxes & fees
14 Aug - 15 Aug
Room for Everyone: Spacious 6BR West Point Retreat
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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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 a coffee maker, 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 4 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. Brewster Public Library and Centennial Golf Club 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.