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Compare 270 Vacation Homes in Brewster with updated reviews, rates, and availability.

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Private kitchen
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (24)
"It was a great couple of days"
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Private kitchen
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (6)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is SAR 1,873
SAR 3,437 total
includes taxes & fees
23 Sep - 24 Sep
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
The price is SAR 1,931
SAR 3,819 total
includes taxes & fees
25 Sep - 26 Sep
Lakeview Estate - Chef's Kitchen - NYC Getaway
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
The front door leads to a porch, patio, and small yard.
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (21)
"Loved it!! "
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (39)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Ossining Vacation Rental Near River, Trails & MTA!
Ossining Vacation Rental | 5BR | 3.5BA | 2,800 Sq Ft | Stairs Required
Ossining Vacation Rental Near River, Trails & MTA!
6.0 out of 10, (2)
"The house was nice & spacious. I do feel like it could use more seating in the living room, considering it can hold up to 11 guests. It would aslo be nice if there were tv's in the guest rooms upstairs. Also, maybe make sure the cleaning crew removes cobweks. "
Ossining Vacation Rental Near River, Trails & MTA!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Bathroom
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (71)
"Hoyse is in a beautiful location and was very clean. The host was responsive and helpful. I would give it 5 stars if it actually had 3 bedrooms."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Majestic RiverView Estate - Breathtaking Views
View of the house (Pool not included)
Majestic RiverView Estate - Breathtaking Views
10.0 out of 10, Exceptional, (2)
"This house was beautiful and perfect for a weekend with friends. There is plenty of space for everyone to spread out and we enjoyed the scenic view from the back deck all weekend. Dan was very responsive from start to finish and we did not encounter any problems throughout our stay. I would highly recommend!"
Majestic RiverView Estate - Breathtaking Views
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (22)
"We had an absolutely fantastic stay at this lakefront property! The outdoor gathering spots are plentiful and perfect for family and friends to enjoy the beautiful surroundings. Whether it was morning coffee on one of the many decks, or simply lounging in the sun, every moment was magical. The kitchen was incredibly well-stocked with everything we needed to prepare meals, which made our stay even more convenient and enjoyable. The entire place was spotless, and it was clear that a lot of care...
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
View of the front and outside of house with driveway and garage.
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
10.0 out of 10, Exceptional, (87)
"Excellent! Loved it! Home was more spacious than we ever thought. The rooms had so much character! Beautiful yard. Perfect setting. We would stay here again."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Garrison Vacation Rental | 2BR | 2.5BA | 1,700 Sq Ft | 1 Step to Enter
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
10.0 out of 10, Exceptional, (20)
"We had a wonderful stay, the property is gorgeous and pristine. Wonderful communication! We'll definitely be back, thank you!"
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
Exterior
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
10.0 out of 10, Exceptional, (7)
"My family wanted a quiet place to stay for a few days. We did some local hiking and sightseeing. The architecture of the house is gorgeous. There were plenty of places to relax both inside and out."
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Front of the house
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
10.0 out of 10, Exceptional, (17)
"Very homey feeling, close to where we needed to go. Easy on and off from highway."
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!
Interior
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!
10.0 out of 10, Exceptional, (3)
"Four night stay with my adult sons and grandson. The owner went above and beyond expectations in making this a great choice. Timely communication, picture and written description accurate, The deck and furnishings are an added bonus along with the hot tub. Three or four types of coffee makers. Coffee, tea and drinks provided. Each bedroom has a large TV that eliminated arguments over which game we would watch. Walking distance to the West Point Museum, Visitor Center and Main...
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!
Modern, Magical Woodsy Escape 1 Hour From NYC
The Lodge in Summer full bloom!
Modern, Magical Woodsy Escape 1 Hour From NYC
10.0 out of 10, Exceptional, (13)
"This day was nothing short of amazing. The tranquility of the home, the land, the amenities, and the township was phenomenal. If you’re on the hustle all the time this is a great place to sit back relax and get in touch with yourself. Everything from the screen porch to the fire pit, The amazing surround sound created such a tranquil environment. If you’re looking to get away from the city life, this is highly recommended not to mention it is not far from the city . Everything is in very close...
Modern, Magical Woodsy Escape 1 Hour From NYC
Historic Connecticut Home w/ Grill & Spacious Yard
Weston Vacation Rental | 3BR | 2.5BA | 2,800 Sq Ft | Stairs Required
Historic Connecticut Home w/ Grill & Spacious Yard
10.0 out of 10, Exceptional, (2)
"House is even cooler than the pictures give it credit for. Beautiful and funky. We really enjoyed our stay!!"
Historic Connecticut Home w/ Grill & Spacious Yard
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
Exterior
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
2.0 star property
10.0 out of 10, Exceptional, (1)
"It is a small property but an excellent location on the lake. Kayaks and paddle boat provided were an added bonus. Owner is very responsive and helpful. Kitchen could be better equipped. Overall a very pleasant and enjoyable stay."
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
Cold Spring Mountain Retreat
Cold Spring Mountain Retreat awaits!
Cold Spring Mountain Retreat
10.0 out of 10, Exceptional, (2)
"My spouse and I really enjoyed our stay. It was spacious, private and the huge windows were incredible. I would not suggest checking in at night. The driveway going up to the house is very dark and uneven terrain, and no lights were on, in or around the house. But once we knew what the road was like, we were a lot more comfortable driving it at night. The house is very very private, which is great. You don't see anyone from the property, and being outside and listening to the trees rustling...
Cold Spring Mountain Retreat
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
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See all available properties in Brewster
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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Other property types in Brewster

The Hideaway
Living area
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 price is SAR 525
SAR 1,032 total
includes taxes & fees
23 Sep - 24 Sep
The Hideaway
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is SAR 653
SAR 957 total
includes taxes & fees
7 Oct - 8 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
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.