Brewster Holiday Rentals

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Holiday Rentals in Brewster

Updated, cozy single family in Fairfield County

9.2 out of 10, Wonderful, (10)
"House was great, hosts were attentive. Enjoyed our stay"
The price is NZ$923
includes taxes & fees
9 July - 10 July
Updated, cozy single family in Fairfield County

Cozy cute Relaxing home

8.8 out of 10, Excellent, (3)
"nice quiet area"
The price is NZ$516
includes taxes & fees
13 July - 14 July
Cozy cute Relaxing home

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

The price is NZ$4,024
includes taxes & fees
9 July - 10 July
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

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 NZ$693
includes taxes & fees
29 July - 30 July
The West Lane Inn - Queen Room

Beautiful New Milford home(1/4mile to Candlewood Lake & Marina+big private pool)

10.0 out of 10, Exceptional, (4)
"We stayed 10 days and the house was perfect for all of us. We were a group of 6 Adults one teen and a 3 year old everything was as listed in the description."
Beautiful New Milford home(1/4mile to Candlewood Lake & Marina+big private pool)

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

10.0 out of 10, Exceptional, (10)
"The house worked very well for our family holiday. Very clean, had everything we needed "
The price is NZ$1,109
includes taxes & fees
9 July - 10 July
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Awesome Lake Home with tons of fun!

2.0 star property
The price is NZ$1,280
includes taxes & fees
13 July - 14 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 NZ$507
includes taxes & fees
9 July - 10 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 NZ$699
includes taxes & fees
16 July - 17 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 NZ$1,429
includes taxes & fees
10 July - 11 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 NZ$1,955
includes taxes & fees
9 July - 10 July
Summer Castle: Pool, Game Room, BBQ - Pet Friendly

3-bedroom and 2 bath cottage across Waterfall

The price is NZ$592
includes taxes & fees
9 July - 10 July
3-bedroom and 2 bath cottage across Waterfall

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 NZ$420
includes taxes & fees
15 July - 16 July
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (23)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is NZ$702
includes taxes & fees
9 July - 10 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 NZ$690
includes taxes & fees
17 July - 18 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 NZ$956
includes taxes & fees
21 July - 22 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 NZ$1,019
includes taxes & fees
9 July - 10 July
Hickory on Willow Lake

Red Cottage - Lakeside Property!

The price is NZ$975
includes taxes & fees
9 July - 10 July
Red Cottage - Lakeside Property!

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

The price is NZ$381
includes taxes & fees
16 July - 17 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, (22)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is NZ$546
includes taxes & fees
20 July - 21 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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 kitchenware, 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.