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Compare 288 Vacation Homes in Brewster with updated reviews, rates, and availability.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (63)
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
9.8 out of 10, Exceptional, (20)
"The property is as wonderful as the pictures show. The kitchen was well stocked with everything needed for us to prepare many meals. We ate outside on the deck overlooking the lake. There is plenty of room to spread out. Three full baths were perfect for us and our adult children. Only downside was there is no bathroom on the main living floor- not a problem for us but it could be if you are traveling with someone who has issues with stairs. It was unanimous we will stay here again."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
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Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, (6)
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (59)
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (38)
"My husband and I greatly enjoyed our stay! We mentioned that we were traveling for our honeymoon and upon our arrival, the host had left a bottle of wine and some little decorations on the dining room table to celebrate our marriage! It was so thoughtful and sweet!! The Vrbo itself was cozy and tidy. We enjoyed cooking in the kitchen and listening to the music of Motown on the cd player. Our host was prompt to respond to messages and answered all questions clearly. We loved staying close to so...
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (22)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Private room in a single family house near Peekskill
9.8 out of 10, Exceptional, (13)
"My wife and I enjoyed our stay. Property owner was very responsive to questions. Home was very clean and inviting. We loved the cats!"
The price is AED 231
AED 525 total
includes taxes & fees
27 Jun - 28 Jun
Private room in a single family house near Peekskill
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (4)
"The inside of the house was AMAZING! Nadia was a great host and very easy to get in touch with. Thank you!"
The price is AED 918
AED 1,381 total
includes taxes & fees
24 Jun - 25 Jun
Contemporary Cozy Cottage
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
10.0 out of 10, Exceptional, (23)
"Jon the owner was extremely communicative in making sure our stay was a success! And he succeeded!! The home was immaculate and fully stocked. We were 2 couples staying over for a convention in a neighboring city, and the accommodations was exactly what we needed. Quiet neighborhood and shopping/eateries was conveniently nearby. There's no question we will stay hear again! Thank you Jon for a wonderful vacation rental experience! 5 stars plus!"
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Modern, Magical Woodsy Escape 1 Hour From NYC
10.0 out of 10, Exceptional, (11)
"Everything about this place was perfect and allowed our family to grieve our loss in comfort and zen"
Modern, Magical Woodsy Escape 1 Hour From NYC
Updated Home w/ Patio Half Mile to West Point
10.0 out of 10, Exceptional, (19)
"We were visiting West Point Academy and wanted a place to stay for our family of five. Perfect location and just what we needed for a couple of nights. Would stay again if we are back in the area!"
Updated Home w/ Patio Half Mile to West Point
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is AED 547
AED 1,065 total
includes taxes & fees
26 Jun - 27 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (19)
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is AED 1,998
AED 3,877 total
includes taxes & fees
2 Jul - 3 Jul
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (17)
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
The Long View of Candlewood Lake
9.8 out of 10, Exceptional, (9)
"Our family had wonderful stay at this beautiful, well-equipped house overlooking Candlewood Lake. It is situated on a large grassy lot with a very private feel in a quiet little neighborhood very close to a small beach and dock. We appreciated having three full bathrooms, and we found the master queen bed quite comfortable. There was a well done welcome guide to the property with clear instructions, as well as information about the local area. In addition, the host was very prompt and thorough...
The Long View of Candlewood Lake
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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.

Other property types in Brewster

The Hideaway
10.0 out of 10, Exceptional, (1)
"We enjoyed our short stay with Renee, who was very helpful! Plenty of room for our XL dogs to walk - ( 90lbs and 188lbs). Thank you for your hospitality! We’ll see you again, if we’re in the area!"
The Hideaway
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is AED 742
AED 1,050 total
includes taxes & fees
24 Jun - 25 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (76)
"Perfect weather for a getaway! Great location to get to get around. Cottage was perfect for us. Fire pit was great to hang out at. Went kayaking across the street. Beautiful lake. However, the access to the lake was a wee bit steep but we are in shape to handle it. All in all it was a great time!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
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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