Brewster Vacation Rentals

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Vacation Rentals in Brewster

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

9.2 out of 10, Wonderful, (7)
"Property was exactly what we were looking for with a group as large as ours (14 people). Plenty of indoor and outdoor space. Great kitchen as well (cooked all of our meals in the house for the whole group)."
The price is ¥126,497
¥221,120 total
includes taxes & fees
Oct 26 - Oct 27
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is ¥27,978
¥45,793 total
includes taxes & fees
Sep 30 - Oct 1
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (193)
"We loved the house, it was very quiet, the view of the lake was beautiful (even though it was rainy and cloudy). The decoration was really nice and it felt super cozy. The host was also very responsive. "
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

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

9.6 out of 10, Exceptional, (35)
"Great place for a quiet stay"
The price is ¥38,544
¥49,158 total
includes taxes & fees
Oct 12 - Oct 13
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (2)
"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

price will make you book twice , luxury living

10.0 out of 10, Exceptional, (1)
"We had a great stay! Room was very open and clean and our host was friendly and welcoming! "
The price is ¥20,665
¥26,717 total
includes taxes & fees
Oct 13 - Oct 14
price will make you book twice , luxury living

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is ¥40,593
¥61,576 total
includes taxes & fees
Sep 29 - Sep 30
Rustic Cabin in Fishkill!

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

10.0 out of 10, Exceptional, (5)
"This condo is located very close to the Garrison train station. It has been designed so that you are never disturbed by the sound of the trains. Really soundproof! There is a beautiful view of West Point across the Hudson River from the balcony and other windows. The kitchen and 2 1/2 bathrooms are modern and well equipped. Matt, the host, has thought of everything when it comes to making his guests feel comfort and st home. The beds were extra comfy and both bedrooms were quite spacious....
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is ¥59,044
¥85,373 total
includes taxes & fees
Sep 29 - Sep 30
Chestnut on Willow Lake

7BD Mention Celebration Welcomes

10.0 out of 10, Exceptional, (1)
"I had a wonderful stay at this house. It was very clean, comfortable, and beautifully maintained.Everything was exactly as described, and I really appreciated the welcoming atmosphere. Even though I only stayed for one day, it was an amazing experience. I would definitely recommend this place and would love to stay again in the future."
The price is ¥88,566
¥141,337 total
includes taxes & fees
Oct 13 - Oct 14
7BD Mention Celebration Welcomes

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (47)
"We really enjoyed totally this Candlewood lake house. it has a fantastic view and a large, beautiful lawn with a fire pit. The owner was a pleasure to work with and she even allowed us to check in a few hours early.The house is fully stocked with everything we needed. The views are fabulous, but if you bring your own boat, the property is at the tip of the lake and the water can be a little rough from other boats going by. "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Candlewood Lake Retreat; Dock, Game Room & Firepit

10.0 out of 10, Exceptional, (47)
"Everything was great! Thank you!"
The price is ¥112,508
¥212,351 total
includes taxes & fees
Sep 28 - Sep 29
Candlewood Lake Retreat; Dock, Game Room & Firepit

Walk to WP Gate + Free Parking!

9.8 out of 10, Exceptional, (16)
"Great property and the hosts were very communicative."
The price is ¥29,377
¥46,356 total
includes taxes & fees
Oct 1 - Oct 2
Walk to WP Gate + Free Parking!

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
The price is ¥18,451
¥37,593 total
includes taxes & fees
Sep 28 - Sep 29
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

10.0 out of 10, Exceptional, (22)
"Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

8.6 out of 10, Excellent, (4)
"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. "
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

10.0 out of 10, Exceptional, (13)
"Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
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

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:

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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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This vacation home rental outside of Brewster is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Brewster?

With 4 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 Centennial Golf Club 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.